Welcome to

CHEM 2OA3

Summer 2014

Organic Chemistry I

Taxol

or

Paclitaxel

1

Avenue to Learn:

Watch Avenue! Contains lecture slides

(incl. this lecture), tutorial problems,

assignments, test info., answers, marks

and much more!

Instructor:

Dr. Paul Harrison

ABB-418 x27290

pharriso@mcmaster.ca

Office hours: before and after class, Tues.

11:30-1, and as announced later

Coordinator:

Greg Bahun

In charge of Laboratories, Tutorials,

Scheduling and Conflict Resolution

bahungj@mcmaster.ca

Office: ABB-301

Office hrs: See Avenue 2

The Course

slide #

• Lectures (2/week) (sl. 4-5)

• Materials &Grades (sl. 6-12)

• Tests: (sl. 13-14)

• One Midterm Test

• Final Exam

• Assignments: (sl. 15-22)

• 2 Written

• Sapling (optional on-line

assignments) & iClicker

• Labs: (sl. 23-33)

• (every week, weeks 2-6)

• Tutorials: (sl. 34)

• (every week, weeks 2-6)

3

Lectures:

Lectures: MDCL 1305; T,R 18:00-21:00;

We will cover Klein, Ch. 1-10, and

spectroscopy (Ch. 15 & 16)

Schedule: (see web site)

For the first approx. 6 weeks, each lecture will

have:

1. Overture: Main thread, Organic structures,

Ch. 1-2-3-4 etc.

2. Intermezzo: Introduction to reactions in Ch.

7-10: head start

3. Sinfonia: Practical aspects, how to purify

organic compounds and determine their

structures (Ch. 15 & 16), presented

through viewing podcasts and iClicker

sessions

After that, return to full-length lectures, Ch. 5

and onwards to 10. 2OB3: continues: 11-25.

Today: intro, Intermez. 1 and Sinfonia Ch.

1 4

5

Podcasts:

• Each 3-hour lecture session will

be available as a podcast

• Intended for review of material,

NOT designed as a substitute for

attending class

• Link will be posted in next day or

so

• May be clickable, if not try cut-

and-paste or another machine

• DON’T send an e-mail when it

doesn’t work first time!

• The podcasts for inverted

classroom are in a SEPARATE

folder on Avenue

Course Materials • Text book: David Klein; Organic

Chemistry 1st ed. (strongly recommended)

• Different packages available through bookstore:

• Binder-ready version (BRV): costs less, but lower (if any) resale value

• Hard cover: costs more, can be re-sold if kept clean

• Both come with access to the study guide as a pdf

• Second ed. is just out: this is OK but cannot support e.g. suggested problems

• Model kit (ONLY the type from the bookstore, must be in plastic for tests)

6

Course Materials (cont.) • iClicker (optional but recommended)

• Lab manual (on sale outside classroom):

• NB cannot use previous version!

• Duplicate Lab book (bookstore)

• Sapling Learning: on-line commercial organic chemistry learning package, recommended for this course. If you opt for Sapling, buy at their website

• Calculators: ONLY CASIO-FX991 will be allowed in tests: needed if you can’t calculate in your head:

3 X 103 X 2 X 10-5

• There are also free on-line learning aids available, such as Reusch’s Virtual Textbook of Organic Chemistry. 7

Course web page:

http://avenue.mcmaster.ca

login: MUGSI userid and password

All relevant course info will be posted

on the Course web page

8

Information on Avenue

• Lecture notes: Lecture notes will be

posted a chapter or two ahead of

where we are in the lectures. ppt and

pdf formats available!

• Lab locations

• Tutorial assignments, locations,

solutions (after tutorials are done)

• Assignments, and solutions

• Exam info, and solutions

• Info on Help Centre and Tutors

• Chat room (No rude comments,

please!)

• Access to podcasts

• Any important announcements

9

Evaluation Chem 2OA3

Assignments (+Click & Sap): 15%

Midterm Test (1): 20%

Laboratories (5): 15%

Final Exam: 50%

Practice Assignments

(Sapling): 0%

In order to pass the course:

• All laboratory work must be

completed with a passing grade

• An overall course mark of 50%

must be obtained 10

Checking Grades

• Marks will be posted on Avenue shortly after assignments, tests or labs have been returned to everyone

• It is YOUR responsibility to check the web site for accuracy

• Applications for mark changes will NOT be accepted beyond one month after the date of posting

11

Grade Corrections

Any changes to term marks must be requested in writing PRIOR to writing the final exam

Submit ALL requests to ABB 301, during Greg Bahun’s office hours. Include the original lab or assignment, a clear indication of the problem, and your student number and email address

Note: Marks for work done in pencil will not be changed

We reserve the right to re-mark any or all parts of the work!

12

Tests Midterm:

Tuesday, May 27th, 6-8 pm

Rooms: TBA, watch web site!

Contains:

multiple choice (~40%)

and written parts (~60%).

Final exam has same format.

Thurs. June 19th, 6-9 pm

Sample test from a previous year are in lab manual, but beware: style of material and questions may vary; also may have arrived at different point.

13

• You get the BEST mark of the weighted average of:

a) Midterm (20%) + Final (50%), or

b) Final Exam (70%) • There is no deferred midterm.

So, if you miss the midterm test, your final grade will automatically be re-calculated to compensate (Final Exam 70%).

• Deferred final is in December • Absolutely no writing at any other

time!

Marks

14

Written Assignments

• There are 2 written Take-Home assignments. (See schedule)

• No late assignments will be accepted, as solutions will be posted within hours of deadline (5:00 pm).

• Written assignments MUST be handed-in in the drop boxes in ABB (around the corner from the CHEM office - ABB-156 - look for signs), in the correct slot, by the deadline.

• Slots are labelled by lab section (L01, L02, etc). There is also one for those exempt from the labs.

15

On-Line Assignments • There are 4 on-line assignments offered

through Sapling Learning.

1) allow most questions that can be done on

paper to be performed on a computer;

2) enable one to draw structures, just as will be

done on an exam;

3) grades instantly and provides feedback via

tutor-like hints, allowing one to keep working

with a question to arrive at the right answer;

4) include detailed answer explanations.

NOTE: use of Sapling is voluntary. If you choose to use

this system, you are REQUIRED to enter your student

number, and this and grade information will be held by (a)

third party(ies) outside McMaster University. By selecting

Sapling, you agree that you are entirely responsible for

any consequences.

Neither the instructor nor Greg Bahun are able to help

with problems related to Sapling. You must contact

Sapling directly.

16

Go to http://saplinglearning.CA

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.

Find your course in the list (listed by school, course,

and instructor) and click the link.

Click the button that says "Send payment via Paypal

or Credit Card" and follow the remaining instructions.

Once you have registered and enrolled, you can log in

at any time.

During sign up - and throughout the term - if you have

any technical problems or grading issues, send an

email to casupport@saplinglearning.com explaining

the issue. The Sapling support team is almost always

more able (and faster) to resolve issues than your

instructor and TAs. 17

18

Sapling evaluation: • Marks will be based on full

participation in each assignment;

failure to fully participate will result

in default up to 0%. This means

attempting AT LEAST 20 questions

per chapter with a reasonable

degree of success (but doesn’t

have to be perfect)

• Sapling marks are based on

Chapters 1-8

• We will also post these as practice

assignments on Sapling Learning

after closure date

• Problems from remaining chapters

will be available but will not used

for marks.

Written Assignment

Dates Summer 2014 Assignment Out

2:30pm

Due

5:00pm

Written Take-Home

Assignment 1

May 14 May 22

Written Take-Home Assignment 2

June 3 June 12

19

On-line Assignment

Dates 2014

Assignment Out

Due

On-line (Sapling) Assignment Ch. 1&2

May 12 May 19

On-line (Sapling) Assignment Ch. 3&4

May 19 June 2

On-line (Sapling) Assignment Ch. 5&6

June 2 June 9

On-line (Sapling) Assignment Ch. 7&8

June 9 June 16

20

21

Participation marks and iClicker: • Spectroscopy is a key practical method to determine

organic structures

• For the first 6 weeks we will cover spectroscopy

twice per week; this will allow you to learn

techniques that you will use in the lab, and to have

lots of time to practice solving spectral problems.

• You will view an on-line lecture PRIOR to coming to

each of the classes (Available on Avenue).

• The last part of the classroom sessions will review

the material you have viewed, and test your

knowledge of spectroscopy through iClicker

questions.

• NOTE: there are LOTS of marks for spectroscopy

during CHEM 2OA3 AND continuing into 2OB3.

Spend serious time on this component!

• Marks available for iClicker:

% correct answers Mark out of 3

80-100 3

65-79 2.5

50-64 2

40-49 1.5

30-39 1

< 30 0

22

Overall Assignment Evaluation:

Assignments Sapling Clicker Total Final

Exam

2 X 6 = 12 3 3 15 * 50

2 X 6 = 12 3 0 15 50

2 X 6 = 12 0 3 15 50

2 X 6 = 12 0 0 12 53

1 X 6 = 6 (MSAF) 3 3 12 53

1 X 6 = 6 (MSAF) 3 or 0 0 or 3 9 56

1 X 6 = 6 (MSAF) 0 0 6 59

And so on; 2 MSAFs

gives you 0-6% out of possible 15%

and hence Final exam is worth 59-65%

* Best 15 out of 18 marks used

Laboratory Check-in

Be prepared to show up to the labs

starting Tuesday May 13th

• Lab Room: ABB-302/306

(ignore your timetable)

• Come to the lab on your scheduled

day, WITH the manual!!!

Failure to complete check-in on time:

see Greg Bahun. This may result in

lost lab time and hence LOST MARKS!

Lab manuals are on sale before the

first two lectures. You MUST have the

current manual. Labs altered. NEW!!!

Contains previous exams! $15.00

23

Labs

Check-in:

Meet your TA

Safety

Check-in

Labs start on:

Tuesday May 13th

5 Labs total

Every Week

24

Exp. 1 May 13-15

Separation of Solids,

Recrystallization & Melting Point

Determination

Exp. 2 May 20-22

Thin Layer Chromatography

(TLC) of Analgesic Drugs &

Column Chromatography.

Exp. 3 May 27-29

Separation and Identification of

Organic Liquids.

Exp. 4 June 3-5

Nucleophilic Substitution Reaction.

Exp. 5 June 10-12

Preparation of meso-Stilbene

Dibromide and its Conversion to

Diphenylacetylene

Experiment Dates

Make-up labs: contact Greg Bahun asap. Ideally done in the same week, otherwise June 17.

25

Lab/Tutorial Scheduling • You MUST visit avenue to obtain

(and check) your:

- LAB section and day

- Tutorial day

- Tutorial room #

N.B. These may be different from

your timetable!!!!!

During lab check-in, your lab station

will be posted in the hall outside of

ABB-302, and later on Avenue

• Ignore what is on your timetable -

the web is what counts!!!

26

Lab Attendance • Students must attend correct

lab period

• You must get a MSAF if you miss a

lab and contact Greg Bahun to

arrange an alternate lab day

• If you act early, make up labs can

be done while the expt. running. If

not, must be done in last week!

• If you have a lab or tutorial conflict,

try to resolve the issue on Solar.

See Greg Bahun if you cannot

resolve the issue with Solar

27

Lab Exemptions

Must have:

•Taken CHEM 2OA3 @ MAC

•Completed ALL labs

•Have 75% or better lab mark

If you satisfy ALL of these criteria

then contact Greg Bahun by

Thursday this week

28

Lab Work

• Some general information and techniques are currently posted on Avenue, make sure to read this information!

• Lab manual: copies for sale, outside classroom

• YOU are responsible for reading and bringing a printed copy of the manual to each lab

• EACH lab has a pre-lab to be completed before entering the lab, some take quite a bit of work, so

don’ t leave them to the last minute!

– Any questions? See Greg during his office hours!

29

Lab Notebooks

• Duplicate Format only!!!

Available in the bookstore

• Finish all results in the lab

period

• TA signs both copies!

• TA keeps the duplicate

• Duplicate returned next lab

period only! (No access to TA

outside regular lab period).

30

Chemistry Lab Safety

• Essential: NO contacts, no shoes

that show ANY part of your foot (ie

sandals, crocs, flats), SOCKS/tights

do not make them any better!

• YOU WILL NOT be permitted to do

the lab

• Recommended: Sneakers

31

Chemistry Lab Safety

• Essential: GOGGLES must be worn at all times! Not just safety glasses

• AGAIN: NO CONTACTS even with goggles!

• No gum

• No shorts/skirts above knee height!

• Long hair ALWAYS tied back!

• You will NOT be permitted to do the lab without the appropriate attire – We work with some nasty stuff!

• ALWAYS wear GLOVES!!!! For your own safety!

• NEVER touch door handles with GLOVES! For everyone’s safety! MARKS WILL BE LOST!

• Recommended: Full length pants, long sleeve shirts and/or lab coat

32

Lab Breakdown

For most labs: Prelab (2 marks)

-Summary of experimental procedure (1/2-full page, 0.5 marks)

include equations, chemicals (amounts), how you will carry out the lab

-Prelab questions (1.5 marks)

Lab Performance (2 marks)

- How prepared you are, follow safety procedures, know what you are doing

Results (6)

- Different for each exp, calculations, graphs, observations, melting points/IR’s etc

33

Tutorials • Every week (weeks 2-6)

Tutorials start:

• Tues. May 13th

• TAs will go through the assigned tutorial questions

• Questions other than the official tutorial questions may be asked at the end of the tutorial, during Q&A.

• We encourage discussion!

34

Help Centre

Hours: TBD (before test and/or exam)

Location: ABB-307 (same hallway as

labs)

The Help Centre TA is there to help with

concepts, not to provide answers for

assignments.

35

Academic Integrity /

Academic Dishonesty

• Academic Integrity is the standard

• Academic dishonesty consists of misrepresentation by deception or by other fraudulent means and can result in serious consequences.

• e.g. the grade of zero on an assignment, loss of credit with a notation on the transcript (notation reads: "Grade of F assigned for academic dishonesty"), and/or suspension or expulsion from the university.

• It is your responsibility to understand what constitutes academic integrity and academic dishonesty – see the course website for a full description.

36

Examples of academic

dishonesty

The following illustrates only four

forms of academic dishonesty:

•Plagiarism, e.g. the submission of

work that is not one's own or for

which other credit has been obtained

•Improper collaboration in group

work, e.g. copying verbatim of other

students' assignments

•Improper use of Sapling and iClicker

•Copying or using unauthorized aids

in tests and examinations

•Ignoring time limits during a test or

exam

37

Academic Dishonesty

• All cases of suspected academic dishonesty will be followed up with the academic integrity officer

• All findings of academic dishonesty will result in a penalty of at least an F (i.e. a zero) for the work in question

• Please refer to McMaster’s policy regarding academic integrity (particularly appendix 3)

• See also the academic integrity statement on the 2OA3 web site

http://www.mcmaster.ca/univsec/policy/AcademicIntegrity.pdf

38

Important!! • It is the student’s responsibility to

ensure that MSAFs are filed on-line and that subsequent medical slips (and other related documents) are filed with your (Associate) Dean’s Office

• For labs, contact Greg Bahun

• For assignments, once filed, assume it’s done, you will not get a response

• You are also responsible for all information in this lecture (see website), even if you are not in class. Failure to follow procedures will result in lost marks!

39

Course Outline

• Available on-line

• Describes the course content

and the tentative schedule for

the lectures

Course Schedule: See web site

40

Pdf and ppt files of lecture notes will

be posted about one week before we

cover that chapter.

If you do not have Adobe Acrobat,

Pdf-Xchange Viewer by Tracker

Software is a good, free pdf viewing

and annotation software.

We will follow Klein’s Organic

Chemistry chapters 1 through 10, +

15 and 16.

41

42

Ch 15: IR

Ch. 16: nmr Ch 9: addition

Ch 1: Bonds

Ch 6: reactivity

Ch 2: groups

Ch 3: acid/base

Ch 4: rings Ch 5: stereo

Ch 8: elimination

Ch 7: subst.

Taxol: what will we learn?