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Chem 341-Online Jasperse Syllabus

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ORGANIC CHEMISTRY I: CHEMISTRY 341 SYLLABUS Online Class - Summer 2017 – 12-week (starts May 16) or 8-week (Jun 13) Sessions

Dr. Craig P. Jasperse web: http://www.ndsu.edu/pubweb/~jasperse/chem341online.htm Office: Ladd 214 e-mail: [email protected] Telephone: (701) 231-5691 (NDSU) (218) 477-2230 (MSUM)

Office Hours: T, W, F 12:00-2:00

Syllabus Contents Page Summary: • Required Text and Materials • Summary of Test Topics • Grading • Quizzes

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Schedule: Detailed Topic Breakdown Which Lectures, Practice-Sets, and Practice Test Videos Go with Each Test

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Testing Options: On-Site at MSUM or Using Proctor 4

How Can I Get off to a Good Start? Go through the Following Steps 5-6

Flexible Course Pacing and Test Scheduling 7

11-Week Schedule (May 16-July 27) 8-Week Schedule (June 13-Aug 4, flexible) 8

6-Week Schedule (May 16-June 22, flexible. Suitable if wanting to also take O2-online) 9

4-Week (May 16-June 15) and 5-Week (May 16-June 19) Schedules (Flexible. Suitable if wanting to also take O2-Face-to-Face section)

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8-Week Schedule (May 16-July 10, flexible) 11

• On-Line Lectures. • Video-playing diagnostic. • How to Download videos as mp4 files, so you don’t need internet connection

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1. Which Videos go with Which Tests? 3. In-Class Notes 2. Why you need to finish the videos well before taking the tests.

4. Practice tests, Answers, and Videos. 5. Practice Problems/Practice Sets.

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Sapling On-Line Homework and How to Register 13, 14 1. Study Strategy 2. “ChemSurvival” Videos 3. Class E-Mail List

15 Book Homework Problems. 15,16 1. Course Help, Office Hours, Communication 2. Classroom Response Plan 3. ACS Accredited 4. Academic Honesty 5. About Online-Organic-Chemistry Website

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Getting Registered for NDSU and the Course, for non-NDSU Students 18 Getting Class Permit To Override Prerequisites (or Take BOTH O1 and O2 Same Summer.) 19 1. Academic and Student Support Services 2. Bison Connection. 3. Technical Skills Expected 4. Technical Support

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1. Accessibility and Disability Services 2. Technology Privacy Policies and Accessibility Statements

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Course Summary 21

1. Overall Course Objectives/Outcomes/Competencies 2. Instructional Materials. 3. Activities/Practice 4. Self-Assessment 5. Graded Assessment (Required Work).

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Individual Test 1, 2, 3, and 4 Expected Skills/Objectives/Outcomes/Competencies 23-26


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ORGANIC CHEMISTRY I: CHEMISTRY 341 SYLLABUS Online Students Summer 2017

12-Week Section: Begins May 16 (Can Start Sooner or Later, Section ID 6300) 8-Week Section: Begins June 13 (Can Start Sooner or Later, Section ID 6701)

Dr. Craig P. Jasperse web: http://www.ndsu.edu/pubweb/~jasperse/chem341online.htm Office: Ladd 214 e-mail: [email protected] Telephone: (218) 477-2230 (MSUM) (701) 231-8469 (NDSU)

Office Hours: T, W, F 12:00-2:00

CHEM 341 . Organic Chemistry I. 3 Credits. Course Description: First semester of a two-semester course in organic chemistry for students in sciences and pre-professional curricula. Prereq: CHEM 122 or 151 (GenChem II). Required Text and Materials: 1) Text: "Organic Chemistry", 8th edition, Carey and Giuliano (Note: an alternative is to buy a cheap version of “Organic Chemistry” by Leroy Wade, 7th edition. See “required text and materials” on website for information. http://web.mnstate.edu/jasperse/Chem341/Required%20Text%20and%20Materials.pdf 2) Solutions Manual: "“Student Solutions Manual to accompany Organic Chemistry” Eighth Edition, by N. T. Allison, R. M. Giuliano, R. C. Atkins, and F. A. Carey.” (The text and solutions manual may be available as a bundle at Varsity Mart. If you use Wade, get solutions manual for them.) 3) On-line “Sapling” homework Problems: You will be required to buy access to an on-line homework system (see later page in syllabus for details.) These problems will be computer-graded, will give you some practice and sometimes tips, and will help to keep you from procrastinating. Test Content Topics and Associated Lectures NDSU Tegrity

Videos

Test 1 Ch 1 Ch 2 Ch 3

Structure Determines Properties Alkanes and Cycloalkanes: Introduction to Hydrocarbons Alkanes and Cycloalkanes: Conformation and cis-trans Stereoisomers

Lectures 1-11 100 pts


Alkyl Halides and An Overview of Chemical Reactions Stereochemistry Reactions of Alkyl Halides; Nucleophilic Substitutions and Eliminations


Test 3 Ch 5 Ch 6

Alkenes: Structure and Preparation: Elimination Reactions Alkenes: Addition Reactions and Other Alkene Reactions



Conjugation in Alkadienes and Allylic Systems Arenes and Aromaticity Reactions of Arenes: Electrophilic Aromatic Substitution


• See later pages for some suggested test schedules, depending on whether you want to complete the course in 4, 5, 6, 8, or 11 weeks. The schedule is flexible.

• See later pages for a longer, more detailed description of course objectives. Grading Summary Tentative grades Tests 1-4 400 points (4 x 100) A 90% Take-Home Paper “Quizzes” 27 points B 80% Online Homework 73 points prorated C 70% D 56% Jasperse website: http://www.ndsu.edu/pubweb/~jasperse/chem341online.htm This will provide links to: Notes for use in class Recorded Lectures Sapling Quizzes Practice Tests Jasperse Schedule Textbook Info Miscellanious Take-Home “Quizzes: http://www.ndsu.edu/pubweb/~jasperse/Chem341/Quizzes/Chem341Quizzes%20Online.html Four “quizzes” will be required, and there are several others that can be used as practice. In the regular class, these will be handed out. For the “online” students, you can print them off of the website. For due dates, lets make them due no later than when you take the test associated with the material being “quizzed”. However, you can also email answers (scanned, in the case of the 3rd and 4th quiz) earlier than that. I may sometimes be able to grade and return them, perhaps with feedback, before the tests.


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Schedule: Which Lecture Videos and Practice-Set Videos Go with Each Test Chemistry 341, Jasperse, Summer 2017 (34 class lectures) Reading

Assignment TEST 1 LECTURES 1. Class Intro; Carbon, Normal Bonding, Lewis Structures 1.1-5 2. Normal Bonding, Lewis Structures, Formal Charge; Resonance; Structural Formulas 1.6-11 3. Structural + Skeletal Formulas; Resonance Structures; Allylic Systems; VSEPR + shape 1.6-11 4. p11, 16-17,12 Shape, Drawing 3D, Mechanisms + Arrow Pushing, Acid-Base 1.12-18 5. p13-15 Acid-Base,Ch 2 p1-2 1.12-18 6. Hybridization, Isomers, Intermolecular Forces, Boiling Points, Solubility 2.1-7, 17,22 7. Functional Groups. 4.1, 4.6 8. Alkanes + Nomenclature. 2.5-14 9. Conformations, Newman Projections, Higher Alkanes, Rings, Cyclohexane Chairs 3.1-6 10. Substituted Cyclohexane Chairs; Alkane Structure Isomers 3.7-13 11. 10 minutes of structural isomers. Then Test 2 material. Catchup Quick skim 2.1-4, Quick skim 3.13-15 Extra Practice Sets+Videos: Acid-Base Practice; 3D-Drawing Practice; Newman Practice;

Cyclohexane Practice; Cyclohexane and Newman Projections Summary

Test 1. Chapters 1-3. TEST 2 LECTURES 11. Introduction to Reactivity Principles. Radical Halogenation of Alkanes. 4.15-19 12. Rates, Activation Energies, Transition States, Multistep Reactions, Stability-Reactivity

Principles 4.15-19

13. Bromination of Alkanes; Radical Stabilities; Mechanism; Practice Problems 4.10,17 14. Practice Bromination Mech; Stability/reactivity: Chirality, Enantiomers, Chiral Centers 7:1-6 15. R and S Classification, Stereochemical Prioritization Rules 7:1-6,8,10 16. Optical Activity; Racemic Mixtures; Symmetry Planes; Diastereomers; Meso Compounds;

Molecules with ≥2 Chiral Centers 7.11-15

17. Alkyl Halides, Introduction/Nomenclature, Properties, Reactivity, and the SN2 Reaction 4.2,4-6 The Sn2 Substitution Reaction. 8.1-5 18. SN2 Reactions 8.1-5 19. More SN2 practice; SN1 Reaction and Mechanism 8.6-12 20. Elimination Reactions 5.14-18 21. Elimination, Practice, how to Distinguish between SN2/SN2/E2/E1 5.14-18 Skip 4.1-14 at this time. Quick skim 7.7,9,16,17 Extra Practice Sets+Videos: Br2/hv Products/Mechanisms Practice; Introductory

Mechanism Practice; Extra Stereochemistry Practice; Extra Test 2 Mechanisms Practice

Test 2. Chapters 4, 7, 8, 5 Test TEST 3 LECTURES 22. Alkenes. Elements of Unsaturation, Hydrogenation, Nomenclature, E/Z 5.1-7; 13.25 23. Synthesis of Alkenes. Use of Bulky Bases. Acid-Catalyzed Dehydration of Alcohols 5.8-13 24. Recognizing Mechanisms. HBr and HOH addn to Alkenes. Markovnikov's Rule 6.1-6,18 25. Antimarkovnikov HBr and HOH Addn. Stereoselective HOH. 6.9-13, p.275 26. Addition of H2, Br2, BrOH, Stereospecificity, Synthetic Design 6.14-17 27. Epoxidation, Dihydroxylation, Ozonolysis 6.19,20 Skim: 5.17, Skim: 6.21 Extra Practice Sets+Videos: Extra Practice; Mechanisms; Alkene Reactions; Synthesis Test 3. Chapters 5, 6 Test TEST 4 LECTURES 28. Conjugation, It's Impact, and Allylic Cations 10.1-7, 11.13,14 29. Allylic Cations, Radicals, Anions, SN2. 1,4/1,2 Addn. Kinetic vs Thermo. Diels-Alder 10.8-17 30. Diels-Alder. Aromatics: Structure, Huckel's Rule, Impact 10.15-17, 11.1-9 31. Aromatic Nomenclature. Electrophilic Aromatic Substitution Reactions. 11.1-9,18-23 32. Electrophilic Aromatic Substitution Reactions. p4-11 12.1-8 33. Advanced Aromatic Substitution Reactions and Synthetic Planning 12.9-16 34. Aromatic Synthesis Design Problems 11.11-12 Skip: 11.10,16,17, 12.17-22 Extra Practice Sets+Videos: HBr Addn to Dienes; NBS Allylic Bromination;

Conjugation-Allylic-Diels-Alder Practice; Aromatic Substitution Mechanisms; Aromatic Substitution Product Prediction/Mechanisms/Synthesis Design

Test 4. Chapters 10, 11, 12 Test


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Testing: Either live at NDSU or Proctored for distance students. Testing will NOT be online. 1. Testing is one aspect of this “online” class that cannot be done online. The nature of organic chemistry

requires drawing/illustrating complex structures for chemicals and electron movement during reaction mechanisms. As such it is not conducive to multiple-choice or short-answer questions that are conveniently viewed and answered online. Further, the flexible scheduling means that some students will take a test before some others; hand-written tests that are proctored and collected upon completion are good for test security.

2. Flexible Test Scheduling: All four tests must be completed by the end of the term (August 4). But there are not fixed tests dates. August 4 is really the only deadline; for completion of everything. To some degree, you can make arrangements to take the tests (within limits) at your own schedule. For example:

o For the May 16 session, you could use all 12 weeks, May 16-Aug 4 o For the June 13 session, you could use all 8 weeks, June 13-Aug 4 o You could complete the course in 6 weeks, May 16-June 24, then use the next 6 weeks (June 25-

Aug 4) to complete Organic II. The 6-week/6-week plan works for finishing both Organic I+II. o You could complete the course in 4 weeks, May 16-June 12, then be ready for the 8-week face-

to-face Organic II course that begins on June 13. (And for the Organic I summer lab.) o You can start as early as you wish, whether for the May 16 or June 13 sections. o You can individualize your schedule. Gone on a missions trip for a week? Gone for a long

weekend for a family vacation or a wedding? You could work ahead as needed to ensure the ability to master all of the material.

o See pages 4-6 in Syllabus for suggested 4, 5, 6, 8, and 11-week schedules. 3. Testing options

a. Testing at NDSU: Any Monday or Thursday, at 12 noon, Ladd 114. • With the flexible test scheduling, different students will be ready for tests at different times.

The next available Monday or Thursday will always be an opportunity. b. Proctored Testing, local to you: Arrange to have your tests proctored, typically at a local college,

library, church or high school. 1) Most colleges have proctoring services. 2) Many public libraries are willing to provide proctoring services 3) For taking proctored tests, YOU will need to find/arrange the proctor; arrange scheduling

with that proctor; email me the name, job, email, and phone number for your proctor; and email me a website for the organization that the proctor is a part of. (For example, if your church pastor is going to proctor your exam, I’d like to look him up to make sure he and the church really exist, before calling him to confirm! J)

4) For proctored tests, I will normally email a copy of the test to the proctor who will print the test. After the test is done the proctor will scan and email me the answers and destroy the printed copy.

5) Because it takes some time to communicate with the proctor, to load and send copies of tests, and for the proctor to print them, it helps to have some advance notice. (Maybe if you email me on Friday night that you’ve got a proctored test set up for Saturday afternoon I’ll get it sent and it will be printed and ready for you; but don’t totally count on it! J)

c. Special Arrangement Testing at NDSU at times other than Monday/Thursday noon. Depending on my schedule and availability, feel free to at least ask if you could take a test at a time that works better for you. I might say yes!

4. Testing time is 90 minutes.

1) Tests are structured so that a well-prepared student should be able to complete a test in 50 minutes or less. But by allowing 90 minutes, that gives extra time to work on problems that you might get stuck on; it provides time to check your work; it provides more space for students who don’t work fast; and it provides enough cushion so that you can just focus on your test without being distracted by worrying about the clock.

2) If you do take proctored tests, you will want to arrange for a 90-minute time block. Proctored Tests will not be returned. Given the flexible asynchronous test-scheduling, I will not be able to send you copies of your graded tests. Local students can see graded test in my office.


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How can I get off to a good start? Go through the following steps.

1. Explore the website(s): http://www.ndsu.edu/pubweb/~jasperse/chem341online.htm • Find the links for each of the following, and in each case open and browse a little bit:

a. Lecture Videos: b. Practice Tests: c. Syllabus: d. Textbook and Materials: e. Class Notes: f. Quizzes: g. Online Homework (“Sapling”): h. Test 1 (and 2 and 3 and 4) materials: i. General Information about how this online organic chemistry course will work

• Links for all of the above, and more, are available on the main website

2. Before the class begins, you’ll want to have done the following: a. Register for the class

• https://www.ndsu.edu/pubweb/~jasperse/Online/Registration.pdf • Jasperse video explaining: http://ndsu.tegrity.com/#/recording/5a3e9083-7d45-42f5-88cc-b02615b1c749?playbackToken=1RZA3KWKYEWZH

b. Order books (used textbook and solutions manual). • Amazon links: http://www.ndsu.edu/pubweb/~jasperse/Chem341/Required%20Text%20and%20Materials.pdf

c. Sign up for Sapling Online Homework: http://www2.saplinglearning.com • Process: https://www.ndsu.edu/pubweb/~jasperse/Chem341/Sapling%20OnLine%20Homework%20Initial%20Instructions.pdf

d. Print Syllabus: https://www.ndsu.edu/pubweb/~jasperse/Chem341/Syllabus-Chem341-online.pdf e. Print Class Notes (double-side print, but best to do full-size):

https://www.ndsu.edu/pubweb/~jasperse/Chem341/Classbook%20Chem%20341/Classbook%20Chem341%20(all-online).pdf • Buy a big 3-ring binder, and 3-hole punch notes so you can keep them all organized.

f. Bookmark the following websites: o Lecture Videos + Homework: https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm o Main website: https://www.ndsu.edu/pubweb/~jasperse/chem341online.htm

g. View the video in which I talk through the syllabus and the course. o Access from Lecture Video site: https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm o Maybe set the play speed at x1.25 or x1.5 or x2 for much of it, and/or fast forward through parts that are

redundant due to having already reviewed the syllabus and other aspects of the course! h. View Jasperse personal introduction video (with face showing! J): https://tegr.it/y/1j6jx

3. Preparing for Test 1

a. Print To-Do Checklist for Test 1: https://www.ndsu.edu/pubweb/~jasperse/Online/Checklist-341Test1.pdf b. Review Skills/Competencies for Test 1: https://www.ndsu.edu/pubweb/~jasperse/Online/Objectives341-Test1.pdf c. Go through the lectures with the printed notes

• https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm • After each lecture, review the material

d. Do lots of Practice/Homework Problems • Many sample practice problems integrated into the lectures • Required Sapling online homework • Do All of the Online Practice sets. (Both main website and lectures website link to same sets.) • Recommended book homework problems as time permits

e. Do All of the Online Practice sets. (Both main website and lectures website link to same sets.) f. Do the required quizzes (there are two for Test 1) g. Do ALL the practice tests h. Arrange proctored testing unless you can test at NDSU.


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4. Basics of how the course will work: • The course will help you master the content through the use of recorded video lectures and detailed

notes; through lots of different practice problems in varying formats; and through multiple practice tests that are similar to the real tests.

• You will have scheduling flexibility in how fast you move and when you schedule your tests. • Tests can be taken via a proctor or at NDSU. • The grade will be 80-85% based on test performance, the rest on required homework and quizzes.


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Dates, Flexible Schedules: Go-At-Your-Own-Pace “Asynchronous”. 1. FLEXIBILITY. You can schedule your own test dates (so long as you finish all by Aug 4, 2017)

2. The “Official” semester start date is either May 16 or June 13, 2017

• You can start earlier, much earlier, if you want, or in between those dates. 3. Semester Completion date: Aug. 4, 2017.

a. You can finish early, and you can start early (or late), but you MUST FINISH BY AUG. 4 4. YOU CAN START EARLY, AND/OR FINISH EARLY. (But must finish by Aug. 4 deadline.)

• I will try to have all course materials ready/online at least a month (usually many months) early • Since lectures and learning materials are online, you don’t need to wait for the official university

semester start dates to actually start. You could start sooner. 5. “GO AT YOUR OWN PACE”/ASYNCHRONOUS. Self-schedule your tests.

• As long as you complete all of the tests by the end of the semester (Aug. 4), test dates are otherwise unfixed/undefined. Some suggested planning schedules are shown on the following pages.

• Online Homework assignments likewise have no fixed due dates, other than end-of-semester • For distance students testing with proctor, you can pretty much set up testing times with your proctor

for whatever time fits your mutual schedules. • For those testing on-campus, I will offer on-campus testing at 12 noon on every Monday and

Thursday. Testing on campus at other times may perhaps be available, by arrangement. • You can adjust on the fly, to some degree. For example, suppose you were planning to take Test 1 on

Thursday May 25, but you realized that if you could study more and take it on the following Monday, you could do much better. That would be OK. (Of course, it’s all too easy to keep “moving tests back” only to run out of time, so be disciplined…)

6. For each individual test, plan to finish the regular lectures a week (or most of a week) prior to when you

actually intend to test, so you have time to practice. Practice makes perfect! • Organic has LOTS of information. Tests will require that you know how to USE the info. • So, doing a lot of practice problems, practice sets, and practice tests is crucial for test preparation.

7. “IT’S EASY TO PROCRASTINATE AND FALL BEHIND. TRY TO SET UP AN AGGRESSIVE

SCHEDULE FOR YOURSELF SO THAT YOU GET DONE EARLY. THAT WAY IF YOU DO HAVE SOME SETBACKS, YOU’LL HAVE SOME CUSHION TIME. • If you schedule to take the full 12 weeks or 8 weeks, that will leave you no cushion in case job or

other issues create a scheduling crisis and leave you unable to prepare adequately. • If you schedule to finish early, that provides some “extra” weeks in case you need them. Or, if you

finish Organic early, wouldn’t it be nice to have some extra summer to enjoy? J

8. PROCTORED TESTS WILL NOT BE RETURNED. Given the flexible test-scheduling, I will not be able to send you copies of your graded tests. Sorry. L

9. The following pages have some info to help with scheduling.


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Suggested 11-week Schedule: For students in the May 16 Section • Geared to be non-rushed, but to get everything done by end of July, and give at least a little August free! • Note: It’s really easy to have a plan but then to fall behind. It is wise to plan complete work a week early.

That provides a little bit of cushion, for cases when you realize you’ll need to spend some extra time on a test. (Especially for the last test, which is typically the hardest.)

Assuming Use of 60-minute NDSU Tegrity Videos

https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm

In Case you Elect to use 50-minute MSUM Panopto Videos http://web.mnstate.edu/jasperse/Online/Lectures350online.html

Test 1 Monday June 5

• Lectures 1-11 • Finish lectures/Sapling by/before Tues, May 30 • Digest/Practice/Integrate rest of week/weekend

Lectures 1-10

Test 2 Thursday June 22

• Lectures 11-21 • Finish lectures/Sapling by/before Fri, June, June 18 • Digest/Practice/Integrate weekend/week

Lectures 11-22a

Test 3 Monday July 10

• Lectures 22-27 • Finish lectures/Sapling by Wed, July 5 • Digest/Practice/Integrate week/weekend

Lectures 22-29b

Test 4 Thursday July 27

• Lectures 28-34 • Finish viewing lectures by Friday, July 21 • Digest/Practice/Integrate rest of week

Lectures 30-38

Notes on the 11-week schedule: • On this schedule you might routinely be going through one lecture video (hour-long) per day, plus reviewing them

and doing Sapling homework. Complete those far-enough in advance of test days so as to give yourself time to put everything together in advance of a test.

• The lecture videos will be available by Feb 14. So you could start early if you wished. • The actual official end-of-semester drop-dead completion deadline is Friday Aug 4, 2017. So, if you registered and got started on the course a week late, for example, you could still finish on time. Suggested 8-week Schedule: For students in the June 13 Section

• Geared towards students who are taking just CHEM341-online, starting June 13 • Note: It’s really easy to have a plan but then to fall behind. • I estimate an average of 20 hours-per-week is an appropriate time allocation for a student whose chemistry

aptitude is good. Assuming Use of 60-minute NDSU Tegrity Videos




• Lectures 1-11 • Finish lectures/Sapling by/before Thursday, June 22 • Digest/Practice/Integrate Friday+Weekend

Lectures 1-10


• Lectures 11-21 • Finish lectures/Sapling by/before Thursday, July 6 • Digest/Practice/Integrate Friday+Weekend

Lectures 11-22a

Test 3 Thursday July 20

• Lectures 22-27 • Finish lectures/Sapling by Sunday, July 16 • Digest/Practice/Integrate Mon-Wed

Lectures 22-29b

Test 4 Friday Aug 4

• Lectures 28-34 • Finish viewing lectures by Monday, July 31 • Digest/Practice/Integrate Mon-Thurs

Lectures 30-38

Notes on the 8-week schedule: • On this schedule you might routinely be going through 6-7 lecture videos (hour-long) per week, plus reviewing

them and doing Sapling homework. Then you’d have several days to study for tests. On a couple of days perhaps you may need to process two lectures, in order to get ahead and give yourself time to put everything together in advance of a test.

• The lecture videos will be available by Feb 14. So you could start early if you wished.


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Suggested 6-week Schedule: For students in May 16 Section • Geared towards students who are taking BOTH CHEM341-online AND CHEM342-online

during the same summer. (6 weeks for 341, then 6 weeks for 342). • Can also be used in conjunction with CHEM342-Face-to-Face-Section (although some of the

Chem 342-Face-to-Face-Section lectures will begin well before you’d finished this 6-week schedule).

• This schedule assumes use of 6 weeks to complete CHEM342-online, beginning on June 25, and finishing on August 4.

• It assumes using the six weeks from May 16-June 23 to complete CHEM341-online. • If you drag beyond 6 weeks for Organic I, it will only leave you less time for Organic II! J • Note: Completing both courses in 12 weeks requires a very serious commitment and a lot of time.

o I estimate an average of 27 hours-per-week is an appropriate time allocation for a student whose chemistry aptitude is good.

o In other words, completing both Organic I and Organic II while also working fulltime at a job is not going to work! J




Test 1 Thursday May 25

• Lectures 1-11 • Finish lectures/Sapling by/before Monday, May

22 (Memorial Day) • Digest/Practice/Integrate Tues+Wed

Lectures 1-10


• Lectures 11-21 • Finish lectures/Sapling by Thursday, June 1 • Digest/Practice/Integrate Fri+Sat+Sun

Lectures 11-22a



Lectures 22-29b


• Lectures 28-34 • Finish viewing lectures by Monday, June 19 • Digest/Practice/Integrate Tues+Wed

Lectures 30-38

Notes on the 6-week schedule: • On this schedule you might routinely be going through two lecture videos (hour-long) per day, plus

reviewing them and doing Sapling homework. On a couple of days perhaps you may need to complete three lectures. You will also need to be using some weekend time, perhaps including Memorial Day weekend.

• The lecture videos will be available by Feb 14. So you could start early if you wished. • Test 3 has fewer lectures to cover, but this schedule has only one week from Test 2 to Test 3. If you

could accelerate earlier on Test 2, for example taking that on Thursday June 1, you’d give yourself more time to prepare for Test 3.

• If you intend to following up this course with Chem 342, the Face-to-Face rather than online section, Tests 1 and 2 in 342 (Face-to-Face) are on Wednesday June 28 and Tuesday July 11.

o So, basically this 6-week schedule has Test 4 taking place 6 days before the first test of Chem 342 Face. (My “live” Chem 342 Face-to-Face class starts on Tuesday, June 13, and the first test is Wednesday June 28). If you went a little faster, and completed Organic I-online a little faster, for example on Monday June 19, you’d then have a good solid week to be fully prepared for the Organic II (Face-to-Face Section) Test 1.

• For some alternative 5-week and 4-week schedules, which might complete Organic I more quickly and give more time for Organic II and/or Organic I lab (on campus), see following page.


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Suggested 4-week Schedule: • Geared towards students who are taking both CHEM341-online and CHEM342-face-to-face during the

same summer. 4 weeks fast for 341, then full 8 weeks for 342 (and lab?). Assuming Use of 60-minute NDSU Tegrity Videos

https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm In Case you Elect to use 50-minute MSUM Panopto Videos http://web.mnstate.edu/jasperse/Online/Lectures350online.html

Test 1 Monday May 22 or Thursday May 26

• Lectures 1-11 • Finish lectures/Sapling by Friday, May 19 • Digest/Practice/Integrate Sat + Sun • Note: Doing special arrangement for Tuesday test

might be helpful, give more time for Test 2, including Memorial Day break?

Lectures 1-10


• Lectures 11-21 • Finish lectures/Sapling by Monday, May 29 • Digest/Practice/Integrate Tues+Wed

Lectures 11-22a


• Lectures 22-27 • Finish lectures/Sapling by Monday, June 5 • Digest/Practice/Integrate Tues+Wed

Lectures 22-29b


• Lectures 28-34 • Finish viewing lectures by Monday, June 12 • Digest/Practice/Integrate Tues+Wed

Lectures 30-38

Notes on the 4-week schedule: • On this schedule you might routinely be going through three lecture videos (hour-long) per day, plus reviewing

them and doing Sapling homework. • You may well need to be using weekend time, including perhaps Memorial Day weekend time. • This schedule has Test 4 taking place during the week that Chem 342 is starting. • You could start using this schedule, but could slow it down if you found yourself falling behind. For example,

move Test 3 back to Monday June 12; and Test 4 to Monday June 19 or Thursday June 22? • I estimate a full-time commitment with an average of 40 hours-per-week is an appropriate/necessary time

allocation for a student whose chemistry aptitude is good. High commitment needed! Suggested 5-week Schedule: Assuming Use of 60-minute NDSU Tegrity Videos

https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm In Case you Elect to use 50-minute MSUM Panopto Videos http://web.mnstate.edu/jasperse/Online/Lectures350online.html

Test 1 Thursday May 25

• Lectures 1-11 • Finish lectures/Sapling by/before Monday, May 22 • Digest/Practice/Integrate Tues+Wed

Lectures 1-10



Lectures 11-22a



Lectures 22-29b


• Lectures 28-34 • Finish viewing lectures by Thursday, June 15 • Digest/Practice/Integrate Fri+Sat+Sun

Lectures 30-38

Notes on the 5-week schedule: • This schedule has Test 4 taking place about a week after my “live” Chem 342-Face-to-Face section starts on

Tuesday, June 13. The first test there isn’t till June 28, so this would allow completion of Organic I with time to then prepare for the first test in Organic II, after which you’d then be right on pace with Organic II.

• On this schedule you might routinely be going through three lecture videos (hour-long) per day, plus reviewing them and doing Sapling homework. You may also need to be using some weekend time, perhaps including Memorial Day weekend time.

• The lecture videos will be available as of Feb 14. So you could start early if you wished. • You could start using this schedule, but if necessary you could slow it down if you found yourself falling behind.


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Suggested 8-week Schedule: For students in May 16 Section • Geared towards students who are taking just CHEM341-online, not also Organic II • Note: It’s really easy to have a plan but then to fall behind. • Note: The course doesn’t actually need to be completed until August 4th.

o This schedule would keep you moving, and hopefully complete with a lot of summer left in which you are free from organic chemistry study obligations!

o Under this schedule, if you fell behind a little bit, or found it took more time than you expected to prepare for a particule challenging test, you’d have some cushion on the back end. If you finish on July 17 instead of August 4, you’re still well ahead of the deadline, for example.

• I estimate an average of 20 hours-per-week is an appropriate time allocation for a student whose chemistry aptitude is good.




Test 1 Tuesday May 30

• Lectures 1-11 • Finish lectures/Sapling by/before Thursday, May 25 • Digest/Practice/Integrate Friday+Weekend

Lectures 1-10


• Lectures 11-21 • Finish lectures/Sapling by/before Thursday, June 8 • Digest/Practice/Integrate Friday+Weekend

Lectures 11-22a



Lectures 22-29b


• Lectures 28-34 • Finish viewing lectures by Thursday, July 6 • Digest/Practice/Integrate Fri+Sat+Sun

Lectures 30-38

Notes on the 8-week schedule: • On this schedule you might routinely be going through 6-7 lecture videos (hour-long) per week, plus reviewing

them and doing Sapling homework. Then you’d have several days to study for tests. So on a couple of days perhaps you may need to process two lectures, in order to get ahead and give yourself time to put everything together in advance of a test.

• The lecture videos will be available by Feb 14. So you could start early if you wished.


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On-Line Lectures: https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm 1. These are normally recorded “Tegrity” lectures from last year’s face-to-face class. 2. Analogous 50-minute “Panopto” lectures. (Content coverage is the same. But these “Panopto”

videos recorded during my fall Organic Chem I class often load faster and more consistently for streaming view, and the podcasts download really easily for offline viewing.) Some students may find these to be more consistent and reliable for viewing.

o http://web.mnstate.edu/jasperse/Online/Lectures350online.html 3. Because the video lectures were actually recorded previously, they often mention Sapling due dates,

test days, or days of the week that won’t make any sense to you. Beware of those! 4. While there are additional study materials and videos, the main lecture videos are normally 60-

minutes in length, which is the duration of the face-to-face class. 5. There are 34 such lectures. 6. “Watching” videos is one thing; understanding everything enough to do everything is quite another!

Getting a good grade in organic chemistry is definitely not a spectator sport! 7. Normally you’ll have wanted to work through all the lectures at least a couple of days before

taking a test, so that you’ve got time to practice, review, integrate, and synthesize all the information, and so that you’ve got time to work through the practice tests, etc..

Do you have the Technical Capacity to play the online videos effectively? And Downloading so you don’t need to have streaming internet. • Note: Most videos were created using either “Tegrity” or “Panopto”. You will want your computer able

to play videos of both types. 1. Tegrity Diagnostic: https://supportu.tegrity.com/#/diagnostic 2. Panopto Test (this doesn’t give you a “diagnostics” page, but should load and play if everything is fine):

• Podcast Panopto: http://coursecast.mnstate.edu/Panopto/Content/Sessions/bad2da5d-3bab-45b9-8ed0-4bfa6a83afdf/4c75611e-583d-4186-8ee2-b0d2ee7613a0-3c28dc83-5922-4d1b-baca-b4c1f16d9b02.mp4

• Streaming Panopto: http://coursecast.mnstate.edu/Panopto/Pages/Viewer.aspx?id=ee9b1109-7b18-4caa-8065-38ab25c74561

• Note: if your internet speed was fine for Tegrity, it will also be fine for Panopto 3. Panopto podcasts can be easily downloaded to your computer so that you can view

without streaming. Tegrity videos can also be downloaded onto your computer, although the download process is a little slower. • If you don’t have consistent fast internet, you may wish to download a whole bunch of videos while

you do have access to fast internet. Then if you’re on an airplane, or at the lake, or visiting grandparents, you’ll still be able to view the videos! J

• Usually if you right-click on the link to a Panopto podcast, you’ll get a menu that includes a chance to save/download the video.

• For Tegrity videos, load the streaming version, and there is a download arrow icon in the lower right corner. (Make sure you aren’t in full-screen mode.)

4. For Pantopo videos, I always list both the streaming version and the podcast. So basically I’ve already converted them into mp4 version for you, which streamlines the download a little bit.

5. If Tegrity videos are having trouble loading or downloading, for whatever reason on a given day, I have Panopto lectures covering equivalent material on my website for Organic II this spring at MSUM. I used essentially the same notes. (Although 50-minute videos were used instead of 60-minute lectures). • http://web.mnstate.edu/jasperse/Chem350/chem350lectures-2014.htm • http://web.mnstate.edu/jasperse/Chem350/Chem350.html

6. For additional syllabus information regarding technical capacity expectations and technical support, see Technical Skills and Technical Support sections later in syllabus. (Page 16?)


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Which Videos go with Which Tests? And why you need to finish the Videos Well before taking the test: • You need to get through all the lectures but then also have time to put everything together.

o If you’re doing the last two lectures the night before taking a test, you’ll not succeed on tests! o You need time to put it all together: review and study everything; practice everything; finish your

required Sapling homework; do more book practice; and do the practice tests! • You’ll want to have finished going through all the lectures at least a couple of days before taking a test

so you’ve got time to actually master everything and become test-success ready. • Assuming Use of 60-minute NDSU Tegrity Videos



Test 1 Lectures 1-10 Lectures 1-10 Test 2 Lectures 10-16 Lectures 11-22a Test 3 Lectures 17-26 Lectures 22-29b Test 4 Lectures 27-34 Lectures 30-38

In-Class Notes: http://www.ndsu.edu/pubweb/~jasperse/Chem341/Classbook%20Chem%20341/Classbook%20Chem341%20(all).pdf I have a very thorough set of notes that can be used in class. Included will be numerous examples and practice problems that I/we will work in lecture together. You should print the notes (NDSU’s printers can print them on both sides of a page), 3-hold punch them, and keep them organized in a 3-ring binder. Many students actually print two copies, one to work through with me during lecture, the other set for working out on their own after lecture. Extra Practice Problems and Practice Sets: http://www.ndsu.edu/pubweb/~jasperse/chem341online.htm Between Sapling homework, assigned/recommended book problems, and practice tests, there are usually a good variety and volume of problems to assess your understanding and to practice and sharpen your skills.

1. However, for each test I have also created a series of additional practice sets to address important learning skills. These are topics where I know students tend to struggle, and where the book and Sapling problems do not provide adequate preparation, and where the Sapling/book problems aren’t perhaps as representative of test problems as I’d like.

2. Students who get A’s and B’s do ALL of these practice problem sets! Absolutely do those. 3. For each of these extra practice sets, you can print them from the website; there are answers provided;

and in each case I have a video created to talk through each problem. 4. Having the video explanation/discussion is helpful for many students in trying to understand the process

for solving problems. Obviously the book problems and Sapling problems don’t have the same kind of commentary available.

Practice tests, Answers, and Videos: http://www.ndsu.edu/pubweb/~jasperse/Chem341/Practice%20Tests/Chem341PracticeTests.html

1. There are three practice tests available for each test which can be printed from the website. 2. These are normally exact copies or slightly edited versions of actual past tests. As such they are

invaluable for getting an idea of what my tests look like, for evaluating whether you are or aren’t well prepared, and for recognizing study areas that need additional attention.

3. For each test, there is also an answer key, and a video in which I discuss each problem. 4. For each test, there is also a “test preview” in which I discuss the format, length, and distribution. 5. Students who get A’s and B’s do ALL of the practice tests! Absolutely do those (without looking at the

answer key or explanatory videos until after you’ve seriously tried on your own. Sapling On-Line Homework: http://saplinglearning.com More details on a later page (the next page). Sapling's modules enable one to interact with 3D models and draw chemical structures. You get instant grading, sometimes response-specific coaching, and detailed answer explanations. The Sapling homework also provides an effort-driven opportunity to earn some points! (Sapling averages are typically much higher than test averages.)


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Sapling OnLine Homework, version 2017 Enrolling at the beginning To get started at Sapling Learning, you need to do two things:

1. Creating accounts. 2. Registering for courses.

The following website should walk you through the process: http://www2.saplinglearning.com/help/higher-education-us/accounts-and-registration Alternatively, many/most students just go straight to the main sapling website, and follow the directions from there: 1. Go to http://saplinglearning.com 2. a. If you already have a Sapling Learning account, log in, click "View Available Courses", then skip to

step 3. b. If you have a Facebook account, you can use it to quickly create a SaplingLearning account. Click "create account" located under the username box, then click "Login with Facebook". The form will auto-fill with information from your Facebook account (you may need to log into Facebook in the popup window first). Choose a password and timezone, accept the site policy agreement, and click "Create my new account". You can then skip to step 3. c. Otherwise, click "create account" located under the username box. Supply the requested information and click "Create my new account". Check your email (and spam filter) for a message from Sapling Learning and click on the link provided in that email.

3. Find your course in the list (listed by school, course, and instructor) and click the link. 4. Select your payment options and follow the remaining instructions. NOTE: Sapling Learning costs $40.00

for a single semester or $60.00 for two semesters. You will be prompted before payment and asked if you would like to purchase two semesters for a discount. You will need to purchase two semesters in advanced to receive the multi-course discount. There is a 14 day grace period to access your courses before payment, and there is a 60 day refund policy. For more information on refunds, visit: http://www.saplinglearning.com/help/?topic=9

******************************************************** Getting on when you’ve already enrolled: 1. Website: http://www.saplinglearning.com/ 2. Login 3. Click on your class 4. If you click on “Activites and Due Dates” in the upper left corner, that will list assignments. ******************************************************** Miscellaneous:

• For online classes, I’m just setting the deadline for midnight CENTRAL TIME, Aug 4. • Take some time with the introduction materials, including the “training assignment” and the

“drawing tips and shortcuts” practice problems. • Once you have registered and enrolled, you can log in at any time to complete or review your

homework assignments. There is no time limit, or a “must finish all problems in one sitting” need. • You can try a problem as many times as you like. The scoring will cost you only 5% of the points

available (per problem) for each incorrect attempt. • On the video lectures website, after each lecture there is a list of which Sapling problems are

appropriate/relevant to that particular lecture. o https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm

• In total, Sapling will count for 73 out of 500 points in the course (15%). (400 course points, 80%, will come from the 4 tests.)

o So, if your overall semester Sapling percentage is 100%, you’ll get 73/73 points. If Sapling % is 93%, you’ll get 68/73; if Sapling % is 68%, you’ll get 50/73, etc.


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Study Strategy: Putting off the extensive information in organic chemistry will only make it harder on you. After each lecture, try to study the day’s notes and work all of the assigned book problems. Some practical study thoughts: 1. General university policy is that an average student in an average class should study for at least two

hours out of class for one hour in class to get an average grade. • Fact: Organic chemistry isn’t really an average class! And do you want an average grade?

2. I suggest reviewing the class notes and in-lecture practice problems ASAP after a lecture, and going through the material at least twice.

3. Many students print an extra copy of class notes, and redo all the in-lecture problems on their own. 4. I suggest working Sapling/book problems associated with the sections covered in class right after that.

These are listed on the lectures website. 5. Do all of the extra practice sets that I provide on the website. 6. Do all of the practice Tests 7. Reading the book: the textbook is a support resource. If you didn’t understand some of the material in

class, the book will frequently have a more complete and detailed discussion that will help you understand things.

8. If you decide you’re not going to take the time to study the class notes, to do Sapling and book problems, and to read the book, which one should you sacrifice first? Possibly some book reading? If you read but run out of time before you get to practice and understand the problems, it’s not a recipe for success.

9. The practice tests are excellent rehearsal for the real tests. • http://www.ndsu.edu/pubweb/~jasperse/Chem341/Practice%20Tests/Chem341PracticeTests.html

10. Some recorded lectures from the summer class may be rushed or not super clear. Alternative lectures covering analogous notes are available from my MSUM online course: • http://web.mnstate.edu/jasperse/Online/Lectures350online.html

“ChemSurvival” Videos by Professor Ron Davis: lots of nice videos!

• Full ChemSurvial site: https://www.youtube.com/user/ChemSurvival/videos?flow=grid&view=0 • Jasperse page that has many of the most relevant ChemSurvival videos linked:

http://www.ndsu.edu/pubweb/~jasperse/chem341online.htm • Professor Davis’s ChemSurvival videos are frequently of very high quality, with excellent molecular-model

displays. In many cases where I’d be displaying molecular models while teaching a face-to-face class, the ChemSurvival videos will do a comparable (or usually better) job of enabling visualization.

• Professor Davis is an excellent teacher and communicator, so there may be times when perhaps things just make better sense with some of his videos and explanation than they do in the regular lecture! If so, please take advantage of whatever enables you to learn and master the material!

Class E-Mail List An email list will be sent to all registered students before the class officially begins. The list probably uses your NDSU e-mail address. If you’d like me to send class-related emails to your normal email rather than your ndsu.edu address, please sent me an email to notify me. [You can also have NDSU emails automatically forwarded to a different address, see https://www.ndsu.edu/its/] Book Homework Problems: See List on Page 13.

• Most of the assigned/recommended book problems represent what I consider to be reasonable test-level problems. I have gone through each problem in the book and selected out those I think are the most representative and practical.

• There may be a few that are trickier than I’d put on a real test, but the majority are ones you ought to be able to do.

• All have worked-out answers in the Solutions Manual. The homework is a great way to practice problem solving, assess your progress, and prepare for tests. Since solutions are available, I will not collect the book homework.

• The few “quiz” assignment problems that I require and grade are no substitute for doing book homework problems! Likewise the on-line Sapling homework will not be sufficient.


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• CHEMISTRY 341 PROBLEMS

• SUMMER 2017 • Dr. Craig P. Jasperse

• These assume you are using Carey and Giuliano version 8. (I have lists that are appropriate if you instead have the 6th or 7th version of Wade. Contact me if that’s your situation, or see: http://www.ndsu.edu/pubweb/~jasperse/Chem341/Other%20Books-Problems%20and%20Readings/Other%20Books-Problems%20and%20Readings.htm

• •

Chapter Recommended Book Problems

Test 1 1

1, 3-8, 10, 12-19, 22, 24-26, 29, 30, 31a, 33, 37, 41, 42, 44, 46, 47, 48, 50-52, 54-57, 60, 65, 69-71, 75-78

2

3-5, 8, 10, 11a,b, 18, 19, 21, 22a,b, 23, 24a,b, 25, 26, 29, 30a,b, 43, 44

3

1-4, 7, 8, 11, 12, 17, 19-24, 27, 28, 32a-e

4 Functional Groups: 35a,b,e,g, 36, 37, 38 Test 2 4

Radicals and Radical Halogenation: 16, 18 (prop. only), 19, 20, 22

7 Stereo: 1, 2, 3c,d, 4, 5, 9, 10, 13, 15, 22, 23, 24, 26, 27, 32-34, 38a,c-f,h-k 8 Substitution: 1-3, 5, 7, 9-11, 15b, 16, 18, 20, 22a-g, 23, 24, 25a-f, 30, 31, 32a,b,d-h, 33a,

34, 40, 47, 49-51

5 Elimination: 22-24, 36, 37a,b,e, 40c,d,g,h,i,j Test 3 5

1, 2, 4, 11-17, 19, 22-24, 28a-h, 30, 33a-d (rank), 34a,b, 36, 37, 40

6 1-5, 8, 9, 15, 19, 21, 26a-h, 27, 28, 32, 34, 36a-f,I,k, 37b-d, 42, 58-61, 63, 65-69 Ch 15:5

Test 4

10 1, 2, 4, 7, 8, 9, 10, 13, 14, 16, 17, 18, 19, 25a, 28a-f, 29, 30, 32, 33, 35, 36a-c, 37, 41, 42, 47, 48, 49, 50

11 1, 2, 3a,c, 13, 15, 18, 21, 24, 25, 26, 33f,I, 34, 36a, 39a-d, h, i, 43a, b, e, f, 44, 45, 46, 47, 50, 51, 59, 60, 61, 63

12 2, 3, 4, 6, 10, 12, 15, 17, 18, 19, 21, 22, 23, 24, 34a-k, 35a-f, 36a,c,d,f, 37, 38, 39a-l,n, 44, 45a-d,g,I,l,m, 46a,c-e, 47a,b,d, 50, 52 Ch 11: 10, 11

•


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Getting Help, Office Hours, Course Communications: 1. Live Face-to-face office hours:

• “Scheduled” Times: T, W, F 12-2:00 (these are days when I’m not giving tests and not grading): • NDSU office: Ladd 214. Phone 701.231.5691 • “Unscheduled” times: Most summer afternoons, I will be in office well beyond 2pm. • When giving tests on Mondays and Thursday 12-1:30pm, I’ll often be available during 12-2pm times at Ladd

114. (To step out and answer a few questions at the table outside the door is acceptable.) • During May and early June, or late afternoons during summer, I may sometimes have office-hours availability

mid-late afternoon at my Minnesota State University Moorhead office (Hagen Hall 407J, 600 11th St South, Moorhead. Phone 218.477.2230), rather than at NDSU. Call or email to check or arrange a visit.

2. Online Virtual Help Options

a. Phone! Often works very well. b. Email: I check often, including nights and Saturdays

o Many students use screen shots, whether for a Sapling homework question, or something in the notes or a practice test or something. This makes it easy to show what you’re having trouble with, and makes it easy for me to focus my answer.

c. Sapling: I can actually look at wrong answers that you’ve submitted, and sometimes screen-shot and email-explain why they’re wrong and what you should have done instead

d. Explain Everything/YouTube video answers (possibility, not a promise! J: o I may explore creating draw-and-talk video recording response to some student questions, and then

sending you the YouTube link to view that explanation. Not sure how effective this will be, or how time-consuming each will be for me to record. So no promises here! J

e. Blackboard Collaborate: o There is some capacity for virtual office visits in which I can share my computer screen.

Classroom Response Plan 1. Quizzes or tests will normally be graded with scores posted by end of the next Monday or Thursday. 2. Emails will *normally* be answered within 48 hours on M-F ("work days"). I will try and will often respond

variably faster than 24 hours. 3. Emails coming in after 10pm will rarely be answered until the following day. 4. I often process class emails on Saturdays as well as M-F, but not on Sundays. 5. If you include a screen shot of the problem or question you have in mind, response will be faster! :) 6. Information about proposed proctor should be sent to me at least 3 workdays prior to the first test with that proctor

to ensure that the test(s) can be sent in time. American Chemical Society approved: North Dakota State University’s chemistry department is approved by the American Chemical Society

• Maybehelpfulinformationfornationalstudentsfromnon-NDSUschools. • If your advisoror recordsofficewonders ifOrganicChemistry atNDSU is legit, theymight ask if it’s

ACS-approved. Academic Honesty The academic community is operated on the basis of honesty, integrity, and fair play. NDSU Policy 335: Code of Academic Responsibility and Conduct (https://www.ndsu.edu/fileadmin/policy/335.pdf) applies to cases in which cheating, plagiarism, or other academic misconduct have occurred in an instructional context. Students found guilt of academic misconduct are subject to penalties, up to and possibly including suspension and/or expulsion. Student academic misconduct records are maintained by the Office of Registration and Records. Informational resources about academic honesty for students and instruction staff members can be found at www.ndsu.edu/academichonesty. For Some Other Questions or Issues About how this Online Organic Chemistry Course will Work, see the following Website:

• http://www.ndsu.edu/pubweb/~jasperse/OnlineOrganicGeneral.htm • The website addresses some common questions students have asked me about the course. • I usually provide some notes, and video in which I talk through some thoughts about each topic.


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Getting Registered for NDSU and for the Course, for non-NDSU Students: Summary: Apply (send official transcripts) > Request Permit > Register AND PAY

• HELP: BisonConnection: https://www.ndsu.edu/bisonconnection/contact/ • Phone: (701) 231-6200, or 1-866-924-8469 (toll free)

1. NDSU application: Apply to NDSU as a “Non-degree seeking student” student before you can register.

a. Create an NDSU account, needed to apply: https://ndusndsu.askadmissions.net/emtinterestpage.aspx?ip=application b. Apply: https://app.applyyourself.com/AYApplicantLogin/fl_ApplicantConnectLogin.asp?id=NDUSNDSU

• There is an application fee. ~$35, as of 2017 c. YOU WILL NEED TO HAVE OFFICIAL TRANSCRIPTS SENT FROM RECENT SCHOOL(S) (2 years)

• For most schools, use: http://www.getmytranscript.com d. NDSU approval usually takes about 2-3 weeks, AFTER all official transcripts have been received. e. Email notification will include a 7-digit NDSU Student ID number. Save/record 7-digit ID! f. Do “New Student Setup”: https://www.ndsu.edu/its/help_desk/account_hub/new_students_activate_your_ndsu_it_services/

• This will set up your login/password for “campus connection”, the site used to register for class, pay, etc. g. Approve “Financial Obligation Agreement”: https://www.ndsu.edu/onestop/accounts/foa/

• Campus Connection login page: https://studentadmin.connectnd.us/psp/NDCSPRD/EMPLOYEE/HRMS/h/?tab=GUEST

• Until you check off on the Financial Obligation Agreement, you won’t be allowed to register for any classes. h. For Jasperse convenience to access: NDSU admission information page with links: http://www.ndsu.edu/admission/admission_information/non_degree_students/

2. Timing, Dates, and Time Deadlines:

a. One section of organic I formally starts on May 16 (2017). Organic II and a second section of Organic I starts June 13. Both early or late starts are feasible for any of these courses. All must complete by August 4 (2017).

b. Class registration for “non-NDSU” students probably opens on Monday, April 24 (2017) c. In practice: Application materials AND OFFICIAL TRANSCIPTS should all have been sent to NDSU by April 25

to safely enable NDSU admission for the May 16 course. (For the June 13 sections, May 23 should suffice.) d. For Jasperse to remember: The drop-dead NDSU admission deadline is normally the Friday prior to the 8-week session. For 2017, that’s Friday

June 9th. If application materials and official transcripts aren’t all in and processed by that day, it’s too late. 3. Class Permit Request: Not having been an NDSU student, you won’t have taken NDSU’s prerequisite courses, and

thus will need a “permit” to actually register for either course. To request the permit(s), email the following information to both: [email protected] and [email protected] a. Your Name b. Your NDSU ID# (you won’t have this until after your NDSU application has been completed (see 1a-d) c. What state (or country) you live in and what school (if any) you attend. d. The class you Want to Take (specify CHEM341 online, or CHEM342 online, or both..).

• Be sure to specify if you want to take BOTH courses or just one. e. Where/how you satisfied the prerequisite(s). Example: “GenChem II at Iowa State, Fall 2016”

4. Register AND Pay: Actually register for the course(s). (2017, probably opens April 18)

a. http://www.ndsu.edu/registrar/registration/ a. Organic I-Online: CHEM341 Class ID: 6300 (for 2017) (May 16-start section) b. Organic I-Online: CHEM341 Class ID: 6701 (for 2017) (June 13-start section) c. Organic II-Online: CHEM342 Class ID: 6301 (for 2017) (June 13-start section)

b. The registration website will direct you through a number of steps. (It will take some time.) c. Until you complete PAYMENT, you’ll never be able to get your grade released. Can pay inside the following: • Campus Connection: https://studentadmin.connectnd.us/psp/NDCSPRD/EMPLOYEE/HRMS/h/?tab=GUEST

5. Tuition+Fees: Unofficially ≤$1100 (As of 2017. May change for later years….) Same for Everybody.

• https://www.ndsu.edu/bisonconnection/accounts/tuition/undergraduate_tuition_part_time/ (See “DCE” rate) • Unofficial flat fee: ($304.69 tuition/credit + $48.92 student fees/credit) x 3 credits = $1060.83 for 2017 • No higher cost for online versus “face-to-face” courses during summer • No higher cost for out-of-state students or international students compared to in-state students • No higher cost for non-NDSU students compared to regular NDSU students.


19

Getting Class Permit (“Override”) to override NDSU Prerequisites. Needed if you are either not a regular NDSU student who took NDSU’s Organic I course, or if you are taking both Organic I and Organic II during this same summer

• Special class permits will often be required in order to register for some of the summer Chem 341/342 courses, whether online or not. This document will first detail what to do, then summarize some of the common situations where a class permit will be needed.

What to do if a class permit is required to register: 1. Email the following information (see #2) to the following two email addresses. (Emailing to me usually

not necessary, but sometimes I’ll need to authorize permission for the chemistry office staff to actually enter that permission into the computer system): • [email protected] • [email protected]

2. Information to include in the email: Include the following information in the emails you send:

a. Your Name b. Your NDSU ID# (you won’t have this until after your NDSU application has been completed (see 1a-d) c. What state (or country) you live in and what school (if any) you attend. d. The class you Want to Take (specify CHEM341 online, or CHEM342 online, or both..).

o Be sure to specify if you want to take BOTH courses or just one. e. Where/how you satisfied the prerequisite(s). Example: “GenChem II at Iowa State, Fall 2016”

• Prereq for Organic I is General Chemistry II • Prereq for Organic II is Organic I

Some situations which might require a special permit. (There may be others). 3. You want to take both CHEM341 and CHEM342.

• A class permit for CHEM342 will be needed. o Doesn’t matter whether CHEM342 is online or face-to-face. o Why: The registration computer blocks Organic II because it doesn’t think you have

completed Organic I yet. § Since you’re registering during the spring, the computer figures you won’t have

completed CHEM341 when the spring semester ends. It’s not programmed to understand that you may be able to do so during the early summer.

4. Prerequisite courses taken at a different school.

a. This will also apply to any non-NDSU student trying to register for CHEM341 • NDSU’s CHEM122, General Chemistry II, is a prerequisite for Organic I. If you took your

general chemistry at a different school, you’ll need a class permit to register for Organic I. • This may also apply to students who transferred to NDSU, perhaps some time ago, but after

taking general chemistry at a different school. b. This will apply to students trying to register for CHEM342 after taking Organic Chemistry I at a

different school. • NDSU’s CHEM341, Organic Chemistry I, is a prerequisite for CHEM342. If you took your

organic chemistry I at a different school, you’ll need a class permit to register.


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Academic and Student Support Services: The Student Support Services Center has resources to assist you with support and encouragement, academic guidance, mentoring, group and individual tutoring services, math and science instruction, reading and writing instruction, accessible tutoring room, and academic success workshops. Visit their website for a list of Services or call 701-231-8028.

• https://www.ndsu.edu/fileadmin/trio/SSS/SSS_flyer_active_flyer.pdf • https://www.ndsu.edu/trio/studentsupportservices/

701-231-8028 NDSU One Stop: https://www.ndsu.edu/onestop/

• NDSU One Stop is an always-open service center (web, phone, email, in-person) that provides information about your student ID card, financial aid, tuition, bill payments, registration, and student records, and has the ability to refer you to other campus resources in the case of questions they can’t answer. Phone: 701-231-6200 (local), 866-924-8969 (toll free). Office 176 Memorial Union.

• Email: mailto:[email protected] Technical Skills: Certain minimum technical skills are expected. I expect you to be able to: 1. Navigate the main course websites and links within:

• Course homepage: https://www.ndsu.edu/pubweb/~jasperse/chem341online.htm • Lectures and Activities Page: https://www.ndsu.edu/pubweb/~jasperse/Online/onlinelectures-341.htm • Practice Tests Page: http://web.mnstate.edu/jasperse/Chem350/Practice%20Tests/Chem350PracticeTests.html • Quizzes Page: https://www.ndsu.edu/pubweb/~jasperse/Chem341/Quizzes/Chem341Quizzes%20Online.html

2. Access and navigate NDSU’s Blackboard course management system • https://bb.ndsu.nodak.edu • In order to enter Blackboard, you’ll need to know your username and password • This where you will access grades • I may add a discussion page, but it does not exist yet.

3. Use and check e-mail regularly. J • The default email address will be your mnstate.edu address. • If you want to use your different, normal address, email me and for class-related emails I can send to your

regular address. But, any university-sourced emails will still go your mnstate.edu address. 4. The ability to take screen shots on your device(s) and attach them to emails

• Often getting good feedback is easiest if you can take a picture of a problem, or something in the notes or in a lecture that you didn’t understand, or an online-homework answer that seems wrong or confusing.

• So the ability to take screen-shot pictures of something on your computer screen and then to email that to me with whatever your related question is helps a lot.

5. The ability to download mp4 video files. (An example of an mp4 podcast is linked below.) • http://coursecast.mnstate.edu/Panopto/Content/Sessions/4579d928-3d74-4738-ba31-260672f613a5/d322606c-c296-4c4c-854f-0bd90e2c2939-beb791c3-86ed-4b73-80f0-aa378ee07ae6.mp4 • For some students who don’t always have fast streaming internet, downloading the podcasts to your computer

allows viewing without fast internet. Technical Support 1. Sapling: mailto:[email protected] 2. NDSU IT Help Desk. No phone, live chat/webex. https://www.ndsu.edu/its/askit/

• https://www.ndsu.edu/its/ • https://www.ndsu.edu/its/services/ • https://www.ndsu.edu/its/askit/

3. Blackboard: https://www.ndsu.edu/its/instructional_services/blackboard/logging_into_bb/ 4. Other problems: mailto:[email protected]


21

Accessibility and Disability Services Office:: Any students with disabilities or other special needs, who need special accommodations in this course are invited to share these concerns or requests with the instructor and contact the Disability Services Office as soon as possible. NDSU Disability Services works to ensure equal access to educational opportunities for students with disabilities. Visit their website, email, call 701-231-8463, or visit their office (Wallman Wellness Center, 170).

• Email: mailto:[email protected] • https://www.ndsu.edu/disabilityservices/

Technology Privacy Policies and Accessibility Statements Links to the privacy policies and accessibility statements for third party software used in this course are listed here. Heavily Used Technologies: 1. Sapling Online Homework

• Accessibility: http://www.saplinglearning.com/ibiscms/help.php?file=accessibility.html • Privacy: http://www2.saplinglearning.com/privacy-policy

2. Blackboard • Privacy: http://www.blackboard.com/footer/privacy-policy.aspx • Accessibility: http://www.blackboard.com/accessibility.aspx

3. Adobe Acrobat Reader • Accessibility: http://www.adobe.com/accessibility/compliance/acrobat-xi-standard-section-508-vpat.html • http://www.adobe.com/accessibility/products/acrobat.html • Privacy: http://www.adobe.com/privacy.html

4. Tegrity Accessibility: • http://createwp.customer.mheducation.com/wordpress-mu/success-academy-

student/accessibility/#.VucsW1JBJ8U 5. Panopto Accessibility:

• http://support.panopto.com/documentation/viewing/accessibilityfeatures 6. Dreamweaver Accessibility: http://www.adobe.com/accessibility/products/dreamweaver.html

Rarely Used Technologies (but may pop up a couple of times or situations.) 7. YouTube Accessibility:

• screen reader: https://support.google.com/youtube/answer/189278?hl=en • captions: https://support.google.com/youtube/answer/100078?hl=en

8. Java Accessibility: http://www.oracle.com/technetwork/articles/javase/downloads-jsp-138220.html 9. Miscrosoft Word Accessibility: http://www.microsoft.com/enable/microsoft/section508.aspx 10. MS products: https://www.microsoft.com/enable/microsoft/section508.aspx Course Summary NDSU Bulletin Course Description: CHEM 341. Organic Chemistry I. 3 Credits. First semester of a two-semester course in organic chemistry for students in sciences and pre-professional curricula. Prerequisites: CHEM 122 or 151 (GenChem II).

Instructor Description: The course is the first semester of a fairly standard two-semester lecture course in organic chemistry, designed for science majors, including those preparing for health professions. Coverage includes nomenclature, structure, properties, and the synthesis, reactions, and reaction mechanisms of alkanes, alkyl halides, alkenes, aromatics, and conjugated systems. Stereochemistry is covered. Reaction types covered include radical halogenation, SN2 and SN1 substitutions, E2 and E1 eliminations, addition reactions to simple alkenes and conjugated dienes, Diels-Alder reactions, and aromatic substitution reactions. Reaction mechanisms are emphasized. Synthesis design/retrosynthesis is emphasized. Structure, stability, stability-reactivity principles, acid-base chemistry, nomenclature, resonance, conjugation, and aromaticity among many other topics, are addressed. (No online lab.) Required work includes tests, online homework, and some “quizzes”. Multiple self-assessment tools are available (sample problems in lecture; online homework problems; textbook problems; extra practice sets; and practice tests.) While this is an online course, it is similar to a traditional course in that videos of actual face-to-face lectures are used (with the advantage of pause-and-rewind). Answers and video explanation of all problems on the practice sets and practice tests are provided. Tests are NOT taken online; hand-written on-paper tests must be taken either at NDSU or using a proctor. The course is go-at-your-own-pace; there are not fixed test dates, and it can be started early.


22

COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following:

• See Test 1-4 Objectives/Competencies as listed on the following pages and on the main course website for more detailed listing of course objectives.

1. Predict and explain Patterns and Properties. Predict and explain patterns in shape, structure, bonding,

hybridization, formal charge, stability, acidity, basicity, solubility, and reactivity for hydrocarbons, halocarbons, alkenes, dienes, and arenes, by understanding and applying concepts of organic chemical structure and bonding and stability.

2. Predict reaction products. Be able to predict products, including stereochemistry, in the reactions of alkanes, halocarbons, alkenes, dienes, and arenes.

3. Classify, explain, and apply fundamental reactions. Be able to recognize, classify, explain, and apply fundamental organic reactions such as SN2, SN1, E2, E1, alkene addition, electrophilic aromatic substitution, 1,2/1,4-additions, ring-opening, and radical halogenation. Be able to apply concepts associated with these general reaction types to product prediction, synthesis design, and reaction mechanism.

4. Retrosynthetic analysis and Synthesis Design. Use retrosynthetic analysis to design efficient multi-step syntheses involving halocarbons, alkenes, and arenes as intermediates or final products

5. Draw Mechanisms. Draw logical and detailed mechanisms for various fundamental reactions of alkanes, halocarbons, alkenes, dienes, and arenes.

6. Apply Resonance and Conjugation. Predict and explain patterns in stability, shape, hybridization, reactivity, and product formation when resonance or conjugation applies to a reactant, intermediate, or final product.

7. Recognize Stereochemistry. Classify molecules as chiral or achiral, identify chiral carbons as (R) or (S), identify relationships between pairs of molecules as enantiomers, diastereomers, or equivalent, and identify when a solution is racemic versus optically active.

8. Apply Stability-Reactivity Principles. Predict, explain, and rank the relative speeds of different chemical reactions by applying structure-dependent patterns in stability combined with application of mechanism recognition.

9. Recognize Structure Relationships Between Chemicals. Be able to recognize relationships between two chemical structures as the same structures, resonance structures, structural isomers, enantiomers, or diastereomers.

10. Use Nomenclature. Provide correct IUPAC names for alkanes, halocarbons, alkenes, and aromatics, including cyclic molecules and including stereochemistry.

11. Recognize and Apply Functional Groups. Classify organic molecules by their functional groups, and identify fundamental properties associates with those functional groups.

12. Demonstrate Understanding in Scenarios Involving Alkanes, Alkenes, Alkyl Halides, Dienes, and Arenes. Answer questions and explain/predict/apply physical properties, nomenclature, synthesis, reactions, mechanisms, and synthesis design/retrosynthesis to scenarios involving alkanes, alkenes, alkyl halides, dienes, and arenes.

Instructional Materials: Detailed class notes; video lectures; in-lecture practice/application problems; supporting supplemental videos; videos talking/teaching through the process for processing/answering each practice problem in the practice sets; feedback and tutorials within Sapling online homework; videos talking through the process for processing/answering each of the practice test case study problems; textbook readings; textbook problems; solutions manual explaining/teaching the process for processing/answering practice problem in the book homework. Activities/Practice: The course includes an extensive and diverse range of activities (“practice problems”) to enable students to apply what they are learning, to practice the types of skills they will need, and to effectively prepare for the tests. These activities include: 1. Extensive in-lecture in-notes practice problems; 2. Practice sets online (≥4 per test; 3. Practice Tests (≥3 per test); 4. Sapling online homework problems; 5. “Quizzes” (open notes, take-home); and 6. Textbook practice problems. Of these the Sapling online homework and the “quizzes” are required and graded. All of the others have answer keys available. For practice sets and practice tests, online videos are provided walking through each problem. Of these, the Sapling online homework and the quizzes will be required and count towards your grade. Self-Assessment: How do you know if you’re mastering the material, and are eventually going to be prepared to score well on the tests? See whether you are consistently understanding and correctly answering the problems in the: 1. In-lecture problems; 2. Practice sets online; 3. Practice Tests; 4. Sapling online homework problems; and 5. Book practice problems. Graded Assessment (Required Work): 1. Sapling online homework 2. Quizzes. 3. Tests.

• The test scores will make up ~80% of the class points. Sapling and the quizzes will combine for the other ~20%.

Chem 341 Jasperse Syllabus

23

TEST ONE SKILLS/OBJECTIVES / OUTCOMES / COMPETENCIES Ch

TEST ONE

Self-Assessment (Some but not all Graded)

Graded Assessment

1 Structure Determines Properties

1. Identify number of bonds and lone pairs for uncharged 2nd-row atoms 2. Draw and interpret Lewis, condensed, and line-angle structural

formulas, including those involving double or triple bonds. 3. Recognize when covalent versus ionic bonding exists 4. Recognize and calculate formal charges and lone pairs given bond

connectivity 5. Populate lone pairs given formal charges and bond connectivity 6. Identify and draw resonance structures, and use them to predict

stabilities. 7. Use arrow-pushing to display electron movement between resonance

structures 8. Use principles of electronegativity to predict bond polarity,

predominant resonance form, anion stability, anion basicity, and acidity 9. Use arrow-pushing to display electron movement in chemical reactions 10. Identify acids and bases, and predict whether an acid-base equilibrium

will favor products or reactants 11. Predict relative acidities and basicities based on structure, bonding,

charge, electronegativity, and resonance of conjugate acid-base pairs.

1. In-lecture in-notes problems 2. Practice sets online 3. Practice Tests 4. Sapling homework problems 5. Book practice problems

1. Sapling homework 2. Quiz 1 and Quiz 2 3. Test 1 4. Final Exam

2 Alkanes and Cycloalkanes: Introduction to Hydrocarbons

12. Predict the hybridization, electron geometry, and approximate bond angles relative to atoms in a molecule

13. Identify sigma versus pi bonds, and rank bond strengths 14. Draw 3-dimensional representation of given molecules, using the hash-

wedge convention. 15. Identify polar and nonpolar molecules, and predict which ones can

engage in hydrogen-bonding. 16. Predict general trends in the boiling points and solubilities of

compounds, based on their size, polarity, and hydrogen-bonding ability.

17. Identify the classes of compounds, the “functional groups”, including hydrocarbons and organic molecules containing oxygen or nitrogen, and draw structural formulas for examples

18. Identify when pairs of structures are related as structural isomers, stereoisomers, resonance structures, or as the same.

19. Correctly name alkanes and cycloalkane 20. Given the name of an alkane, draw the structure and give the molecular

formula


1. Sapling homework 2. Quiz 2 3. Test 1 4. Final Exam

3 Alkanes and Cycloalkanes: Conformation and cis-trans Stereoisomers

21. Use Newman projections to compare the energies of alkane conformations

22. Draw best and worst Newman projections relative to any individual bond

23. Use torsional and steric strain terminology to explain differences in rotation barriers and in Newman-projection stabilities

24. Identify, name, and draw cis and trans stereoisomers of di-substituted cycloalkanes

25. Compare the energies of cycloalkanes, and explain ring strain 26. Draw accurate cyclohexane chair conformation, including cis- or trans-

di-substituted cases, and including “left-” and “right-handed” chair conformations

27. Illustrate and identify axial versus equatorial substituents on cyclohexane chairs; and predict the most stable conformations of di-substituted cases.

28. Based on chemical formula, identify whether an alkane is cyclic or acyclic

29. Given a chemical formula for an alkane, draw and name structural isomers


1. Sapling homework 2. Test 1 3. Final Exam


24

TEST TWO SKILLS/OBJECTIVES / OUTCOMES / COMPETENCIES Ch TEST TWO Self-Assessment

(Some but not all Graded)

Graded Assessment

4 Alkyl Halides and An Overview of Chemical Reactions

1. Draw the mechanism and explain the energetics of the propagation steps in the free-radical halogenation of alkanes

2. Based on the selectivity of halogenation and the varying stabilities of 1º, 2º, 3º, and allylic radicals, predict the products of halogenation of hydrocarbons

3. Apply principles of bond strength to predict whether overall reactions or individual steps within a multi-step mechanism are exothermic or endothermic, are favorable or unfavorable, and use bond strengths to predict the energetics of reactions.

4. Given a rate law, predict how the rate would vary with changes in solute concentrations or solvent volume.

5. Use energy diagrams to discuss transition states, activation energies, intermediates, and the rate-determining step of a multistep reaction

6. Rank the stabilities of different radical, carbocations, or anions and describe or explain the structural features that stabilize them.

7. Use reactant and product stability-reactivity principles in conjunction with structural factors to compare the relative reactivities of different reactions

8. Predict and explain variations in bond strengths


Sapling homework Quiz 3 Test 2 Final Exam

7 Stereochemistry

9. Classify moleculas as chiral or achiral, and identify mirror planes of symmetry

10. Draw a mirror image for any molecule 11. Identify chiral carbons, and name them using the (R) and (S)

convention 12. Identify relationships between pairs of molecules as enantiomers,

diastereomers, or equivalent 13. Identify and identify meso compounds 14. Draw all stereoisomers for a given structure 15. Identify when a solution is racemic versus optically active 16. Identify when a chemical reaction will give a racemic versus optically

active product Recognize and explain how various physical properties might vary or not vary for enantiomers, or for diastereomers.


Sapling homework Quiz 4 Test 2 Final Exam

8 Reactions of Alkyl Halides; Nucleophilic Substitutions and Eliminations

17. Correctly name alkyl halides, and identify halocarbons as 1º, 2º, 3º, allylic, vinyl, or aryl

18. Predict the products of SN2 reactions, including stereochemistry. 19. Predict the products of SN1 reactions, including stereochemistry. 20. Predict the products of E1 and E2 reactions, including stereochemistry. 21. Use Zaytsev’s Rule to predict which structural isomer will predominate

in E2 or E1 reactions. 22. When a halocarbon reacts, identify when SN2 or E2 reactions occur, or

when SN1 or E1 reactions will occur, and predict the major products. 23. Draw mechanisms for any of SN1, SN2, E1, or E2 reaction 24. Rank the relative rates of substitutions or eliminations reactions, based

on differences in substrate, base/nucleophile, leaving group, or solvent. 25. Predict whether a reaction will be first-order or second-order 26. When possible, predict predominance of substitution or elimination 27. Identify reactants that could product target chemical products 28. Design multi-reaction synthesis design sequences to convert

hydrocarbons to more highly functional derivatives


Sapling homework Test 2 Final Exam


25

TEST THREE SKILLS/OBJECTIVES / OUTCOMES / COMPETENCIES TEST THREE Self-

Assessment (Some but not all Graded)

Graded Assessment

5 Alkenes: Structure and Preparation: Elimination Reactions

1. Calculate “elements of unsaturation” (“EU”) for any formula. 2. Determine the number of alkenes and rings present in any formula, given its

chemical formula and hydrogenation information. 3. Draw possible structural isomers for a chemical, given formula and

hydrogenation information. (“Detective” problems.”) 4. Draw and name all alkenes with a given molecular formula 5. Use the E-Z and cis-trans systems to name stereoisomers 6. Use heats of hydrogenation to compare stabilities of alkenes, or use stability

patterns for alkenes to predict heats of hydrogenation or heats of combustion 7. Predict relative stabilities of alkenes and cycloalkenes, based on structure and

stereochemistry 8. Predict the products of E2-elimination for haloalkanes, reactions (Zaytsev

versus Hofmann elimination), depending on whether the base used is bulky or normal.

9. Predict the distribution between E2-elimination and SN2 substitution for reactions of haloalkanes

10. Predict the major alkene products (Zaytsev elimination) when alcohols undergo acid-catalyzed dehydration.

11. Propose and draw detailed mechanisms for E2-elimination reactions of alkyl halides, and for acid-catalyzed E1 elimination of alcohols.

12. Propose and design effective single-step and multistep syntheses of alkenes. (Synthesis design problems.)

1. In-lecture problems 2. Practice sets online 3. Practice Tests 4. Sapling homework problems 5. Book practice problems


6 Alkenes: Addition Reactions and Other Alkene Reactions

13. Predict the product when an alkene react with a hydrogen halides 14. Predict the products when alkenes react with HBr/peroxides 15. Predict the product when an alkene react with H2O/H+ 16. Predict the product when an alkene undergoes hydroboration/oxidation 17. Predict the products when alkenes undergoes oxymercuration/demercuration 18. Predict the product when an alkene undergoes hydrogenation 19. Predict the product when an alkene reacts with Cl2 or Br2 20. Predict the product when an alkene reacts with Cl2 or Br2 in the present of

water 21. Predict the product when an alkene undergoes expodiation, with or without

water present 22. Predict the product when an alkene undergoes ozonolysis 23. In all of the above reactions, include effective consideration of reaction

orientation (Markovnikov versus anti-Markovnikov orientation), and stereochemistry

24. Predict when a reaction will produce achiral versus chiral products 25. Predict the correct stereoisomers for stereospecific reactions. 26. Draw detailed logical mechanisms for alkene reactions with HBr, H2O/H+,

Br2, or Br2/H2O. 27. Use retrosynthetic analysis to solve multi-step synthesis design problems

involving alkenes as intermediates or final products 28. Use clues provided by products of reactions such as ozonolysis to determine

the structure of an unknown alkene 29. Determine the stereochemistry of a starting alkene, given reactants and the

product stereochemistry.




26

TEST FOUR SKILLS/OBJECTIVES / OUTCOMES / COMPETENCIES TEST FOUR Self-

Assessment (Some but not all Graded)

Graded Assessment

10 Conjugation in Alkadienes and Allylic Systems

1. Recognize when conjugation applies, how it impacts chemical stability, and use it to predict and rank stabilities of various substances

2. For compounds containing nitrogen atoms, determine what the nitrogen atom hybridization and shape is; determine what the lone pair hybridization is; and predict whether the nitrogen basicity is normal or low

3. Predict and rank how various reactions and their reaction rates are impacted by conjugation/resonance, whether in a reactant or an intermediate or a product, for example in SN1 reactions, radical reactions or acid-base reactions

4. Predict the products of hydrogen halide additions to conjugated dienes. 5. Identify 1,2 vs 1,4 addition products in hydrogen halide additions to

conjugated dienes 6. Identify thermodynamic versus kinetic products 7. Predict the products of allylic radical bromination reactions. 8. Draw mechanisms for addition reactons or SN1 reactions proceeding

through allylic cations 9. Draw resonance structures for allylic cations, radicals, or anions 10. Predict the products of Diels-Alder reactions, including

stereochemistry; and when the dienophile is disubstituted. 11. Identify reactants involved in Diels-Alder reactions, allylic bromination

reactions, and hydrogen halide additions to conjugated dienes.



11 Arenes and Aromaticity

12. Name aromatic molecules, and draw structures given names 13. Use the polygon rule to draw the energy diagram for a cyclice system

of p orbitals, and fill in the electrons to show whether a given compound or ion is aromatic or anti-aromatic

14. Use Huckel’s rule to identify whether a given structure is aromatic, anti-aromatic, or non-aromatic, including heterocycles and ions

15. Apply understanding of how aromaticity or anti-aromaticity in a reactant, intermediate, or product impacts reactivity and reaction rates, for example in SN1 reactions or acid-base reactions

16. For compounds containing nitrogen atoms, determine what the nitrogen atom hybridization and shape is; determine what the lone pair hybridization is; and predict whether the nitrogen basicity is normal or low



12 Reactions of Arenes: Electrophilic Aromatic Substitution

17. Predict products for the common electrophilic aromatic substitutions: halogenation, nitration, sulfonation, alkylation, and acylation.

18. Predict the position of substitution involving rings that have more than one substituent.

19. Draw the mechanisms for the electrophilic aromatic substitution reactions.

20. Draw resonance structures for the cationic intermediates involved in electrophilic aromatic substitution reactions on substituted rings.

21. Identify and apply which substituents are electron donors and electron withdrawers; activators versus deactivators; and ortho/para directors versus meta directors for electrophilic aromatic substitution reactions.

22. Predict products and utilize in synthesis design problems the common aromatic support reactions: reduction of nitro groups to amino; reduction of acyl group to 1º alkyl; oxidation of alkyl groups to carboxyl; desulfonation; allylic bromination.

23. Retrosynthesis/Synthesis design: design syntheses towards specific aromatic targets with appropriate ortho, meta, or para subsitution, by using appropriate reactants and appropriate reaction sequencing



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