unit 11: organic chemistry notes & cw · pdf fileunit 11: organic chemistry notes & cw...

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Unit 11: Organic Chemistry Notes & CWThe bold, underlined words are important vocabulary words that you should be able to define and use properly in explanations. This is a study guide for what you will be tested on throughout the year. The objectives are divided into categories of “Knowledge” (what you have to know) and “Application” (what you have to be able to do).

I. ORGANIC CHEMISTRY

Knowledge Application

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o Organic compounds contain carbon atoms which bond to one another in chains, rings, and networks toform a variety of structures.

o Organic compounds are named using specific IUPAC rules and can be represented using molecularformulas, structural formulas, or condensed structural formulas.

2.

o Hydrocarbons are organic compounds that containonly carbon and hydrogen. *The C–H bonds areconsidered to be nonpolar covalent bonds.*

o Saturated hydrocarbons contain only single C–Cbonds.

o Unsaturated hydrocarbons contain at least onedouble or triple carbon-carbon bond.

o Draw structural formulas for alkanes,alkenes, alkynes, given their IUPAC names

o Name a hydrocarbon (IUPAC rules), given itsmolecular formula, structural formula, orcondensed structural formula

o Identify whether a hydrocarbon is saturatedor unsaturated, given its IUPAC name,structural formula, condensed structuralformula, or general formula (see Table Q)

3. o In a multiple covalent bond, more than one pair of

electrons is shared between two atoms. In a structuralformula, each line represents TWO shared electrons

o Determine the TOTAL number of electronsshared in a covalent bond

o Determine the number of electron PAIRS(lines) shared in a covalent bond

4.

o A functional group is a group of atoms attached to anorganic compound that gives distinct physical andchemical properties to organic compounds having thatgroup attached to it.

o Organic acids, alcohols, esters, aldehydes,ketones, ethers, halides, amines, amides, andamino acids are types of organic compounds thatdiffer in the type of functional group they have.

o Compounds that have the same functional group havesimilar physical and chemical propertiesEx: all esters have pleasant odors, all organic acids donate H+

ions in solution, all alcohols have low boiling points, etc.

o Identify different kinds of functional groupso Classify an organic compound based on its

structural formula, condensed structuralformula, or IUPAC name

o Draw a structural formula with the functionalgroup(s) on a straight chain hydrocarbonbackbone, given the correct IUPAC name forthe compound

o Name any of these organic compounds, giventheir structural or condensed structuralformulas (see Table R)

5. o Isomers are organic compounds that have the same

molecular formula, but different structures andproperties.

o Determine if two compounds are isomers,given their molecular formulas, structuralformulas, condensed structural formulas, ornames

6. o Types of organic reactions include: polymerization,

substitution, fermentation, addition, combustion,esterification, and saponification. *P.S. FACES*

o Identify types of organic reactions, givenbalanced chemical equations

o Determine missing reactants or products in abalanced equation, given the type of reaction.

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Lesson 1: What is an Organic Compound?

Objective: To define organic compounds and their properties. To compare and contrast structure of the different kinds of hydrocarbons.

Although originally defined as the chemistry of biological molecules, organic chemistry has since been redefined to refer specifically to carbon compounds — even those with non-biological origin. Some carbon molecules are not considered organic, with carbon dioxide being the most well known and most common inorganic carbon compound, but such molecules are the exception and not the rule. Major sources of organic compounds are: petroleum, coal, wood, plants, & animals.

Organic chemistry focuses on carbon and following movement of the electrons in carbon chains and rings, and also how electrons are shared with other carbon atoms and other atoms. Organic chemistry is primarily concerned with the properties of covalent bonds and non-metallic elements, though ions and metals do play critical roles in some reactions.

The applications of organic chemistry are myriad, and include all sorts of plastics, dyes, flavorings, scents, detergents, explosives, fuels and many, many other products. Read the ingredient list for almost any kind of food that you eat — or even your shampoo bottle — and you will see the handiwork of organic chemists listed there.

Unsaturated organic compounds contain at least one double or triple covalent bond. In a double covalent bond, two pairs of electrons are shared between two atoms; in a triple bond, three pairs are shared. Isomers are molecules that have the same molecular formula, but different structural formulas and different physical and chemical properties as a result. Hydrocarbons tend to be nonpolar molecules. Vander Waals forces are the weak attractive forces between nonpolar molecules. The attraction increases with increasing molecular mass, resulting in higher melting/boiling points. Since Hydrocarbons are nonpolar they tend to be insoluble in water, but soluble in other nonpolar solvents like lamp oil (hexane).

Because they are Nonelectrolytes, they are POOR Conductors of Electricity. They DO NOT dissociate to form ions in solution. They are molecules (covalent compounds).

They have LOW melting points – due to their weak intermolecular forces. The melting point generally increases with an increase in the number of carbons. They are Combustible (flammable), which is why we use them for energy.

Recall: Carbon forms 4 COVALENT BONDS which may be single, double or triple

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Types of bonds

Single Bond – single covalent bond in which they share 1 pair of electrons. (2 e-)

Double Bond – carbon atoms may share 2 pairs of electrons to form a double bond.

Triple Bond – carbon atoms may share 3 pairs of electrons to form a triple bond

Because carbon can bond to itself, it makes it possible for there to exist a large number of organic molecules, even more numerous than inorganic compounds.

Lesson 2: Hydrocarbons

Hydrocarbons are Organic compounds that ONLY contain CARBON and HYDROGEN The homologous series defines the three types of hydrocarbons that can exist. They are a group of organic compounds with similar properties and structures. TABLE Q gives the general formula and examples (name and structure).

Hydrocarbons are defined by the types of bonds that exist between the carbon atoms in the molecule.

Saturated hydrocarbons contain SINGLE bonds ONLY!! They contain the maximum # of hydrogen possible (saturated).

Alkanes are a Group of SATURATED hydrocarbons with the general formula: CnH2n+2 . They are used as burning FUELS

Example: propane

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Naming Alkanes

Count up the # of carbons

Use TABLE P to determine the prefix

Name ends in -ANE

Example: C5H7

5 carbons (5 = pent)

All single Bonds (ANE)C5H2(5)+2

Name: PENTANE

Unsaturated hydrocarbons contain multiple bonds. They have at least 1 double or triple bond between carbons (not saturated with hydrogens)

Alkenes are a group of UNSATURATED hydrocarbons with the general formula: CnH2n. They contain 1 Double Bond and always twice as many hydrogens as carbons in formula Example:

Naming Alkenes Naming alkenes is the same as naming alkanes except the ending is –ENE.

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Example C5H10


Contains Double Bond (ENE)C5H2(5)

Name: PENTENEAlkynes are a group of UNSATURATED hydrocarbons with the general formula: CnH2n-2 They contain 1 TRIPLE BOND.

Naming Alkynes Naming alkenes is the same as naming alkanes except the ending is –YNE.

Example C5H8


Contains TRIPLE Bond (YNE)C5H2(5)-2

Name: PENTYNE

How to determine the type of hydrocarbon using Table Q:

1. Count up the number of carbons2. If the # of Hydrogen are double the # of carbons it’s an alkene3. If more than double its an alkane, less than double it’s an alkyne

Example: C5H12 (12 is more than double 5 so it’s an alkane)

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Lesson 3: Structural formulas

Objective: To compare molecular, structural and condensed formulas of hydrocarbons

Watch this: Click here this video IS the lesson!!!!! The notes are a short summary.

There are three different ways we can represent organic molecules.

1. MOLECULAR FORMULA-shows the # OF ATOMS of each ELEMENT in a compound; least informative formula.Example: C2H6

2. STRUCTURAL FORMULA- diagram of the molecular structure of compound

Example:

3. CONDENSED STRUCTURAL FORMULA- each carbon is written separately followed by atoms bonded to it.Example: CH3CH3

Drawing structural formulas of Alkanes

Use TABLE P and TABLE Q to determine # of CARBON and HYDROGEN

Remember each Carbon must have FOUR bonds

Drawing structural formulas of Alkenes

Same as Alkanes except….o If there are more than 3 carbons you need to give the location of DOUBLE BONDo Always START numbering the carbons at the end CLOSEST to the double bond to give the bond the

lowest number

https://youtu.be/8EpaTZVHJYA

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Drawing structural formulas of Alkynes

Same as alkenes except you add a TRIPLE BOND

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Classwork 11-1, 11-2, & 11-3:

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Propyne C3H4

Pentane C5H12

Hexyne C6H10

Heptene C7H12

Octane C8H18

Molecular Formula

General Formula

Series Structural Formula Condensed Structural Formula

Name of Compound

C5H12 CnH2n+2 Alkane CH3CH2CH2CH2CH3 Pentane

3- Heptyne

CH3CH2CH3

CH3CH=CHCH2CH3

C9H20

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Molecular

Formula

General

Formula

Series Structural Formula Condensed Structural

Formula

Name of

Compound

1-Octene

C8H18

C9H18

CH3CH2CH2CH2CH2CH2CH3

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Lab Activity - Homologs

Purpose: To create models of various organic molecules and compare.

Materials: Reference Table P & Q, Model kit, Lesson 1 & 2 Notes

1. How many valence electrons does carbon have? _____ How many times does it bond? _____2. How many valence electrons does oxygen have? _____ How many times can it bond? _____3. How many valence electrons does hydrogen have? _____ How many times does it bond? _____

Procedure:

Part One: Single Bonds

1. Make a model of CH4 using the model kit.2. Replace one hydrogen atom with a carbon atom and add additional hydrogen atoms until every bond

of each carbon atom is filled. Draw and name this molecule with reference to tables P and Q.3. Repeat step two until you have created 5 molecules.

Part Two: Double Bonds

1. Make a model of C2H4 using the model kit.2. Replace one hydrogen atom with a carbon atom and add additional hydrogen atoms until every bond


1 2 3

4 5

1 2 3

4 5

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Part Three: Triple Bonds

1. Make a model of C2H2 using the model kit.2. Replace one hydrogen atom with a carbon atom and add additional hydrogen atoms until every bond


Part Four: Functional Groups

1. Using your model kit construct the following molecules, draw them, name them and identify theirfunctional group (use table R).

1 2 3

4 5

C3H7OHH C4H9OOHH CH3OC2H5

C3H7OCH3 C2H5OHOH C5H11CHOO

CH3COC3H7 C2H5COC2H5 C2H5COOHOH

HCOOHH C2H5COOC3 C6H13COOC2H5

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Questions:

1. When constructing your first set of molecules, every time a carbon atom was added, how manyhydrogen atoms were added?

2. Does this first set of molecules represent a homologous series? Explain.

3. What do the name of the series and the name of the members in the first series have in common?

4. When constructing your second set of molecules, every time a carbon atom was added, how manyhydrogen atoms were added?

5. Does this second set of molecules represent a homologous series? Explain.

6. What do the name of the series and the name of the members in the second series have in common?

7. When constructing your third set of molecules, every time a carbon atom was added, how manyhydrogen atoms were added?

8. Does this third set of molecules represent a homologous series? Explain.

9. What do the name of the series and the name of the members in the third series have in common?

10. In part one, you created a molecule with only one carbon atom to start the series. Why didn’t thesecond and third series start with only one carbon atom?

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Lesson 4: Isomers and branched alkanes

Objective: To use branched alkanes to represent isomers

Isomers are compounds with the SAME MOLECULAR formula but different STRUCTURAL FORMULA. They havedifferent properties because of the difference in structure. The more carbons there are in the molecule then the morepossible isomers that can exist.

1. Isomers of Alkanes are known as branched alkanes

Watch this: Click here this video IS the lesson!!!!! The notes are a short summary.

ALKYL GROUPS are carbon chain branches sticking off the main parent chain of hydrocarbons. This is how isomers areusually seen.

Naming Alkyl groups

Count # of carbons in alkyl group (branch) Use prefix (TABLE P) Add Suffix “yl” to prefix

Ex. –CH3 (Methyl)

https://youtu.be/2GUdbv9hstk

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Follow the steps:

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2. Isomers of alkenes and alkynes just have the double or triple bond in a different location.

Example: Two isomers of Butene C4H8

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Classwork 11-4:

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Classwork 11-4:

Lab Activity - Naming the Isomers of Hydrocarbons

PROBLEM:

How do you identify isomers of hydrocarbons?

INTRODUCTION:

Although many hydrocarbons have the same formula, they are not the same compound. They areisomers. Constructing models and drawing pictures makes it clear that the isomers of acompound have different structures. They also have different names. In this laboratoryinvestigation, you will construct, draw, and name all of the isomers of a hydrocarbon.

MATERIALS (per group):

Molecular Model Kit

PROCEDURE:

1. Obtain a molecular model kit containing colored spheres to representatoms, and sticks or springs to represent bonds.

2. Construct a model of C7H16 as follows: Use black spheresto represent carbon, yellow spheres to representhydrogen, long sticks to represent bonds betweencarbons, and short sticks to represent bonds betweencarbon and hydrogen. Attach the spheres together insuch a way that all the holes are filled.

3. Based on the molecular model you construct, draw thestructural formula for the compound in the spaceprovided on the next page.

4. Name the type of compound as follows: If it has allsingle bonds, it is an alkane and has the suffix "ANE"in the name. If it has one double bond, it is analkene and has the suffix "ENE" in the name. If it hasone triple bond, it is an alkyne and has the suffix"YNE" in the name.

5. The rest of the name of the compound is determined bycounting the number of carbons in the longest chain,and the number, length, and location of the sidechains. Each of these is indicated by using one of the prefixes inthe table below:

NumberPrefix

Carbons in Main Chain Carbons in side chain Number of side chains Location of side chains

1 meth methyl - 1

2 eth ethyl di 2

3 prop propyl tri 3

4 but butyl tetra 4

5 pent pentyl penta 5

6 hex hexyl hexa 6

7 hept heptyl hepta 7

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Figure 2. Methyl butane

6. Write the name of the isomer below the structuralformula following the rules described on the previouspage. See the example of methyl butane (C5H12) drawn tothe right. The main chain is called "BUTANE" because itis four carbons long and has all single bonds. Thebranch is called "METHYL" because it is one carbon long.There are no other prefixes or numbers because there isonly one branch in the only possible location it can be.

7. Repeat steps 2-6, using a different arrangement ofcarbons. Continue repeating steps 2-6 until you haveconstructed, drawn and named all the possible isomers ofC7H16.

OBSERVATIONS:

Drawings and Names of the Isomers of C7H16

CONCLUSIONS:

1. How many different isomers of C7H16 are there?

2. Why might these isomers have different properties if they have the same simple formula?

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1. Whichformularepresentsanunsaturatedhydrocarbon?

A) C)

B) D)

2. Whichorganiccompoundisasaturatedhydrocarbon?A) ethyne C) etheneB) ethanol D) ethane

3. Whichformularepresentsahydrocarbon?A) CH3CH2CH2CHOB) CH3CH2CH2CH3C) CH3CH2CH2COOHD) CH3CH2COOCH3

4. Whichstructuralformulacorrectly representsahydrocarbonmolecule?A) B)

C) D)

5. Insaturatedhydrocarbons,carbonatomsarebondedtoeachotherbyA) singlecovalentbonds,onlyB) doublecovalentbonds,onlyC) alternatingsingleanddoublecovalent

bondsD) alternatingdoubleandtriplecovalent

bonds

6. Whatisthegeneralformulaforthemembersofthealkaneseries?A) CnH2n C) CnH2n+2B) CnH2n–2 D) CnH2n–6

7. Inwhichgroupcouldthehydrocarbonsallbelongtothesamealkeneseries?A) C2H2, C2H4, C2H6B) C2H2, C2H4, C4H8C) C2H4, C2H6, C3H6D) C2H4, C3H6, C4H8

8. Amoleculeofbutaneandamoleculeof2-butenebothhavethesametotalnumberofA) carbonatoms C) hydrogenatomsB) singlebonds D) doublebonds

9. Adoublecarbon-carbonbondisfoundinamoleculeofA) pentane C) penteneB) pentyne D) pentanol

10. Themultiplecovalentbondinamoleculeof1-buteneisaA) doublecovalentbondthathas6shared

electronsB) doublecovalentbondthathas4shared

electronsC) triplecovalentbondthathas6shared

electronsD) triplecovalentbondthathas4shared

electrons

11. Giventheformula:

WhatistheIUPACnameofthiscompound?A) 2-pentene C) 2-pentyneB) 2-butene D) 2-butyne

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12. Giventhestructuralformula:

WhatistheIUPACnameofthiscompound?A) propane C) propeneB) propanone D) propanal

13. Whatisthecorrectformulaforbutene?A) C4H4 C) C4H6B) C4H8 D) C4H10

14. Whichgeneralformularepresentsthehomologousseriesofhydrocarbonsthatincludesthecompoundl-heptyne?A) CnH2n-6 C) CnH2n-2B) CnH2n D) CnH2n+2

15. Whichcompoundisanunsaturatedhydrocarbon?A) hexanal C) hexaneB) hexanoicacid D) hexyne

16. Giventhestructuralformula:Whatisthetotalnumberofelectronssharedinthebondbetweenthetwocarbonatoms?A) 6B) 2 C) 3D) 4

17. Whichformularepresentspropyne?A) C3H4 C) C3H6B) C5H8 D) C5H10

18. WhatisthenameofacompoundthathasthemolecularformulaC6H6?A) butane B) buteneB) benzene D) butyne

19. Twosubstanceshavedifferentphysicalandchemicalproperties.Bothsubstanceshavemoleculesthatcontaintwocarbonatoms,oneoxygenatom,andsixhydrogenatoms.ThesetwosubstancesmustbeA) isomersofeachotherB) isotopesofeachother

C) thesamecompoundD) thesamehydrocarbon

20. ThethreeisomersofpentanehavedifferentA) formulamassesB) molecularformulasC) empiricalformulasD) structuralformulas

21. Moleculesof1-bromopropaneand2-bromopropanedifferinA) molecularformulaB) structuralformulaC) numberofcarbonatomspermoleculeD) numberofbromineatomspermolecule

22. Whichstructuralformularepresentsamoleculethatisnot anisomerofpentane?A)

B)

23. Which compound is an isomer of pentane?A) butane C) propaneB) methylbutane D)methylpropane

24. Whatisthemaximumnumberofcovalentbondsthatcanbeformedbyonecarbonatom?A) 1B) 2 C) 3D) 4

25. Whichstructuralformulacorrectlyrepresentsanorganiccompound?

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26. Atomsofwhichelementcanbondwitheachothertoformringandchainstructuresincompounds?A) CB) Ca C) HD) Na

27. Whichelementhasatomsthatcanbondwitheachothertoformlongchainsorrings?A) carbon C) nitrogenB) oxygen D) fluorine

28. Whichelementmustbepresentinanorganiccompound?A) hydrogen C) oxygenB) carbon D) nitrogen

29. Organiccompoundsthatareessentiallynon-polarandexhibitweakintermolecularforceshaveA) lowvaporpressureB) lowmeltingpointsC) highboilingpointsD) highelectricalconductivityinsolution

30. AcharacteristicofmostorganiccompoundsisthattheyA) havelowmeltingpointsB) havehighmeltingpointsC) aresolubleinwaterD) conductelectricitywhendissolvedin

water

31. Ingeneral,whichpropertydoorganiccompoundsshare?A) highmeltingpointB) highelectricalconductivityC) readily soluble in waterD) slow reaction

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FUNCTIONAL GROUPS = organic compounds that form when one or more hydrogens in a hydrocarbon are replaced; atom/group of atoms that give the organic compound certain characteristics/properties

Use the following table when YOU HAVE MORE THAN JUST A HYDROCARBON!

Lesson 5: Functional groups & Table R

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1. Halides (Halocarbon)= one or more hydrogen atoms on a hydrocarbon isreplaced by a HALOGEN (group 17 element such as F, Cl, Br, I) Same rules as naming hydrocarbon branches except now you must

state the location of the halogen along the carbon chain (lowest #location)

May also contain branches (same naming rules as before)

Examples:

2. Alcohols = one or more hydrogen atoms on a hydrocarbon is replaced byan –OH (hydroxyl) group

“-e” ending on hydrocarbon is replaced by “-ol” Same rules as naming halogens, except now you must state the

location of the hydroxyl along the carbon chain (lowest # location) Alcohols (covalent molecules) are NOT BASES (ionic)

NONELECTROLYTES POLAR & WATER SOLUBLE

CAUTION: organic acids also have an –OH in their functional group!

1-propanol (see Table R)

2-chloropropane 2,2,3-trichlorobutane

Lesson 6: Halides & Alcohols

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3. Ethers = look for -O- bridging two hydrocarbon chains name two branches off the –O- (alphabetical if necessary) then add

“ether” to the end of the name if both branches are the same use “di (insert type of branch) ether” NEVER USE #’S in name since there are only 2 sides to the O!

Examples:

4. Aldehydes = carbonyl group (-C=O) found at END of hydrocarbon chain “-e” at end of alkane is replaced by “–al” very similar to ketones – BEWARE!

Examples:

methyl ethyl ether butyl propyl ether

Propanal (see Table R)

Lesson 7: Ethers, Aldehydes & Ketones

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5. Ketones = carbonyl group (-C=O) located on an INTERIOR CARBON atom(within the chain)

“-e” at end of alkane replaced by “–one” must cite the location of the –C=O in the carbon chain often used as solvents Very similar to aldehydes – BEWARE!

Examples:

Organic Acids = carboxyl group found at terminal carbon

Hydrocarbon ending “–e” replaced with “–oic” then add “acid” assecond word in the name

Generate ____________ in solution ==> ____________________

Examples:

propanoic acid (see Table R)

2-pentanone (see Table R)

Lesson 8: Organic Acids, Esters, Amines & Amides

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7. Esters = contains connecting parent chain to branch

hydrocarbon chain containing is the parent chain replace the “-e” at the end of the name with “-oate.”

hydrocarbon chain single-bonded to oxygen is the branch name as you would any other branch

known by their strong fragrant aromas (ex: wintergreen)

Examples:

8. Amines = “N” alone (w/ only H’s) seen within the carbon chain Amine group can be a branch off the parent chain (like a methyl branch)

Number the carbon with the amine group, name the parent chain,replace the “-e” at the end of the name with “-amine.”

Amine group can be “buried” within the carbon chain Name exactly the same as you would an ether, except substitute

the word “amine” for “ether.” (See Table R)

Examples:

ethyl butanoate propyl methanoate

H NH2 H H H │ │ │ │ │

H—C—C—C—C—C—H │ │ │ │ │ H H H H H

ethyl methylamine1-propanamine

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Amino Acids = organic molecules containing both a carboxyl and an amine group

don't worry about naming these, just recognize them can also contain additional functional groups

Ex: Box the functional groups in the examples below:

General Formula Cysteine Threonine

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9. Amides = contains group; can be at the terminal position or connecting a parent chain to a branch

Examples: (terminal position)

Examples: (connecting parent chain to branch)

propanamide (see Table R) butanamide

methyl ethanamide ethyl propanamide

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For each of the following identify the Functional Group and then name each compound using Table R.

Classwork 10-5 thru 10-8:

For the following compounds, determine the family and draw the compound:

Name Family StructuralFormula CondensedFormula

Butanoic acid

Methanal

Butanamide

3-iodo octane

Methyl pentanoate

Ethanol

2-heptanone

Diethyl ether

2-pentanol

Ethanoic acid

2-propanamine

Hexanal

Ethyl methanoate

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Lesson 9:ORGANIC REACTIONS - Combustion, Substitution & Addition

1. Combustion (AKA Oxidation) = a HYDROCARBON (alkane, alkene,or alkyne) is burned in the presence of OXYGEN (O2 is a reactant)to produce water and CO2. Must know this reaction cold!

Ex:

________ + ____________ ________________ + ________

2. Substitution = 1+ HYDROGEN atoms in a saturated alkaneREPLACED/substituted by another atom/group

Ex:

________ + ____________ ________________ + ________

3. Addition = atoms/groups are added at the multiple (double ortriple) bond ofan unsaturated hydrocarbon to become a saturatedhalocarbon (halide); 2 reactants turn into ONE LARGER PRODUCT

Ex:

____________________ + ____________ _______________

________ + _____ _______ + _______

________ + _____ __________

________ + _____ _______ + _______

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4. Esterification = an ester is created, putting an alcohol and acid together bymeans of dehydration polymerization "PRODUCES AN ESTER AND WATER.

Ex:

__________________ + ___________ _________ + ________

5. Saponification = making SOAP. Ester is always on left side; esterreacts with inorganic base to produce alcohol (glycerol) and soap;producing soap and glycerol from a fat and a strong base

_________ + _________ ___________ + _________

must use Table R to identify these! Reaction is VERY COMPLICATED looking

__________ + ______ __________ + _____

Lesson 10: Organic Reactions - Esterification, Saponification & Fermentation

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6. Fermentation = the production of alcohol and CO2 from a sugar. Inthis specific case, yeast contains an ENZYME that breaks GLUCOSEinto CO2 an ETHANOL; Must know the example cold!

Ex:

_________ _________ + __________________

7. Polymerization = FORMATION OF LARGE MOLECULES calledpolymers (organic compounds made up of chains of smaller unitscovalently bonded together called monomers); SMALL MOLECULES(MONOMERS) JOIN TOGETHER to form a larger molecule(polymer). Polymers are large molecules with unique characteristics.Examples of natural polymers: starch, cellulose, protein. Examplesof synthetic polymers: plastics, nylons, rayons, polyester

Addition Polymerization = unsaturated monomers join bybreaking their double or triple bonds to bond with one another;makes long chains!

__________ _________ + _____

Lesson 11: Organic Reactions - Polymerization

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Condensation Polymerization = monomers join by REMOVINGH2O; hydroxyl group (-OH) and ether/ester linkage join tocreate H2O

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Matchthereactiontoitsname:

___ 1. Addition a. C13H28 à C8H18 + C2H4 + C3H6

___ 2. Substitution b. C3H8 + 5O2 à 3CO2 + 4H20

___ 3. Combustion c. (C17H35COO)3C3H5 + 3 NaOH à C3H5(OH)3 + 3C17H35COONa

___ 4. Cracking d. C6H12O6à C2H5OH +CO2

___ 5. Polymerization e. n(CH2CH2) à (CH2CH2)n

___ 6. Fermentation f. C2H6 + Cl2 à C2H5Cl + HCl

___ 7. Esterification g. C3H6COOH + C2H5OH à C3H6COOC2H5 + H2O

___ 8. Saponification h. C3H6 + I2 à C3H6I2

Namethereaction:

9. A saturated alkane reacts with fluorine _____________________________

10. Small alkene chains connect to form larger alkane chains _____________________________

11. Sugar is decomposed to form an alcohol _____________________________

12. Large hydrocarbons are heated and break into smaller fragments _____________________________

13. An unsaturated hydrocarbon reacts with bromine _____________________________

14. An alcohol and an organic acid are reacted _____________________________

15. A base is added to a fat molecule to form a soap _____________________________

16. Hydrocarbons are burned in the presence of oxygen _____________________________

17. Another name for hydrogenation* _____________________________

18. Another name for halogenation* _____________________________

Drawallorganicreactantsandproducts.Thennameandgivetheformulaforthemissingsubstanceinthereaction.Givethereactiontype.

19. C2H4 + F2 à ________________ Rxn: __________________________

Classwork 10-9 thru 10-11:

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20. C3H6 + H2 à ________________ Rxn: __________________________

21. C2H6 + Cl2 à ________________ + HCl Rxn: __________________________

22. C4H10 + Br2 à ________________ + HBr Rxn: __________________________

23. CH4 + O2 à ______ + H2O Rxn: __________________________

24. C3H8 + O2 à CO2 + ______ Rxn: __________________________

25. C6H12O6 à 2CO2 + 2________________ Rxn: __________________________

26. C8H18 à C6H12 + ________________ Rxn: __________________________

27. C2H5OH + C3H7COOH à H2O + ________________ Rxn: __________________________

28. C5H10 + F2 à ________________ Rxn: __________________________

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Unit Review: Organic Chemistry

Place a checkmark next to each item that you can do! If a sample problem is given, complete it as evidence.

_____1. I can still do

everything from Unit 1.



















_____12. I can define organic

compound, saturated

hydrocarbon, unsaturated

hydrocarbon, and isomer.

Definitions:

organic compound

saturated hydrocarbon

unsaturated hydrocarbon

isomer

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_____13. I can expand a

condensed structural formula

to show the structural formula

of an organic compound.

Draw the complete structural formula for CH3CH2CH2CH2CH3.

Draw the complete structural formula for CH3CHCHCH3.

_____14. I can state the name

and symbol of the element that

is capable of forming rings,

chains, and networks.

The element that is capable of forming rings, chains, and networks is

______________________. Its symbol is_______________.

_____15. Given the formula, I

can determine if a compound is

a hydrocarbon or not.

_____16. Given the name, I can

use Reference Table P to

determine how many carbons

atoms are in a compound.

Determine how many carbon atoms are in each of the following

compounds:

decane________________________

ethene___________________________

3-nonene______________________ 1-

pentyne__________________________


use Reference Table Q to

determine to which class of

hydrocarbons a compound

belongs.

Determine the homologous series of hydrocarbons to which each of the

following belongs:

decane________________________ 2-

decene__________________________

3-nonene______________________ 1-

pentyne__________________________


determine if the hydrocarbon

is saturated or unsaturated.

Determine if each of the following is a saturated or unsaturated

hydrocarbon.

decane________________________

ethene___________________________

3-nonene______________________ 1-

pentyne__________________________

45


can determine to which

homologous series a

hydrocarbon belongs.

Determine the homologous series of hydrocarbons to which each of the

following belongs:

belongs to the _______________________ series.

belongs to the ________________________ series.

belongs to the ________________________ series.


can determine if a

hydrocarbon is saturated or

unsaturated.

Determine if each of the following is a saturated or unsaturated

hydrocarbon.

CH3CH2CH2CH3__________________________

CH3CHCHCH3_____________________________

_____21.Given the name, I can

use Reference Table Q to

determine how many hydrogen

atoms the hydrocarbon

contains.

Determine the number of hydrogen atoms in each of the following.

decane________________________ 1-

butene__________________________

3-nonene______________________ 1-

pentyne__________________________

_____22. Given a list of

compounds, I can determine

which ones are isomers.

46

_____23. Given a structural

formula, I can use Reference

Table R to identify to which

class of organic compounds a

substance belongs.

_____24. I can use Reference

Tables P & Q and IUPAC

nomenclature to name simple

hydrocarbons.

Name the following hydrocarbons.

47

_____25. I can use Reference

Tables P & R and IUPAC

nomenclature to name simple

compounds in any of the

classes of organic compounds.

Name the following organic compounds.

_____26. I can list and describe

the 7 types of organic

reactions.

Fermentation This type of organic

reaction results from a reaction of _____________________ to form

_________________________________ and

________________________. It typically requires a catalyst, in the form

of an enzyme to occur.

Substitution This type of organic

reaction happens when _____________________________

hydrocarbons

replace one of the _____________________ for some other element

(often a halide).

48

Combustion

reaction a ____________________________________ reacts with

___________________ to form ___________________________ and

_______________________. It is an exothermic reaction.

Addition In this type of organic reaction

an _______________________________________ becomes a

__________________________________________ when the double

bond breaks and two atoms of another element (often a halide) are added.

_____26. I can list and describe

the 7 types of organic

reactions.

Polymerization In this type of organic

reaction many __________________ are linked together to form a

__________________________. A generalized form of this reaction

looks like this…..

Esterification In this type of organic

reaction an ______________________ reacts with a

________________________________ to form an

___________________ and

___________________________. The products of this reaction are

typically fragrant.

Saponication In this type of organic

reaction a ____________ reacts with a ____________________ to form

______________________. You can really “clean up” if you remember

this organic reaction.

49

_____27. Given an equation, I

can identify the type of organic

reaction that is occurring.

50

1. Giventhestructuralformulasfortwoorganiccompounds:

ThedifferencesintheirphysicalandchemicalpropertiesareprimarilyduetotheirdifferentA) numberofhydrogenatomsB) numberofcarbonatomsC) molecularmassesD) functionalgroups

2. Organiccompoundsthatareessentiallynon-polarandexhibitweakintermolecularforceshaveA) lowvaporpressureB) highelectricalconductivityinsolutionC) lowmeltingpointsD) highboilingpoints

3. Giventhestructuralformulas:

Whichtwoformulasrepresentcompoundsthatareisomersofeachother?A) B and D C) A and BB) A and C D) C and D

4. WhichcompoundisanisomerofCH3CH2OH?A) CH3COOH C) CH3CH2CH3B) CH3COCH3 D) CH3OCH3

5. Whatisthetotalnumberofcarbonatomsinamoleculeofethanoicacid?A) 1B) 2 C) 3 D) 4


WhatistheIUPACnameofthiscompound?A) methylpentanoateC)pentanolB) pentanal D) pentanoicacid

7. Giventhethreeorganicstructuralformulasshownbelow:

Whichorganiccompoundclassesarerepresentedbythesestructuralformulas,asshownfromlefttoright?A) ketone,aldehyde,alcoholB) ester,organicacid,ketoneC) ketone,organicacid,alcoholD) ester,aldehyde,organicacid

8. Whichofthesecompoundshaschemicalpropertiesmostsimilartothechemicalpropertiesofethanoicacid?A) C3H7COOH C) C2H5COOC2H5B) C2H5OH D) C2H5OC2H5

9. Whichcompoundisanalcohol?A) methanol C) butaneB) ethyne D) propanal

10. Giventheformulasoffourorganiccompounds:

Whichpairbelowcontainsanalcoholandanacid?

A) a and b C) c and dB) a and c D) b and d

11. WhatistheIUPACnameforthecompoundthathasthecondensedstructuralformulaCH3CH2CH2CHO?A) propanol C) butanalB) propanal D) butanol

Practice test

51

12. TheorganiccompoundrepresentedbythecondensedstructuralformulaCH3CH2CH2CHOisclassifiedasanA) ether C) alcoholB) ester D) aldehyde

13. WhatistheIUPACnameofthecompoundwiththefollowingstructuralformula?

A) propanone C) butanoneB) butanal D) propanal

14. WhichLewiselectron-dotdiagramrepresentschloroethene?A) C)

B) D)


ThiscompoundisclassifiedasanA) aldehyde C) alcoholB) amide D) amine


Thisstructuralformularepresentsamoleculeof

A) aketone C) analdehydeB) anester D) anaminoacid

17. Whichformularepresentsanether?A) C)

B) D)

18. Giventhebalancedequationforanorganicreaction:

C2H2 + 2Cl2 à C2H2Cl4 Thisreactionisbestclassifiedas

A) fermentation C) esterificationB) substitution D) addition

19. Giventheincompleteequationrepresentinganorganicadditionreaction:X(g)+Cl2(g)à XCl2(g)

WhichcompoundcouldberepresentedbyX?A) C3H8 C) C4H10B) CH4 D) C2H4

20. Giventheequation: CH4 + Br2 à CH3Br + HBr

Whichtypeofreactiondoesthisequationrepresent?

A) substitution C) polymerizationB) addition D) hydrogenation

21. Whichorganicreactionproducesrubberandplastics?A) polymerization C) fermentationB) esterification D) saponification

22. Whichtypeofreactionisrepresentedbytheequationbelow?

A) saponification C) esterificationB) fermentation D)polymerization

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23. Giventhereaction:

ThisreactionisanexampleofA) hydrogenation C) fermentationB) saponification D) esterification

24. Whenbutaneburnsinanexcessofoxygen,theprincipalproductsareA) COandH2O C) CO2andH2OB) CO2andH2 D) COandH2

25. Inwhichreactionissoapaproduct?A) saponification C) polymerizationB) addition D) substitution

26. Whatarethetwomainproductsofafermentationreaction?A) ethanolandwaterB) ethanolandcarbondioxideC) sugarandwaterD) sugarandcarbondioxide

27. Baseyouranswertothefollowingquestionontheinformationbelow.

Theincompleteequationbelowrepresentsanesterificationreaction.ThealcoholreactantisrepresentedbyX.

DrawthestructuralformulaforthealcoholrepresentedbyX.

28. Agasolineengineburnsgasolineinthepresenceofexcessoxygentoformcarbondioxideandwater.Themaincomponentsofgasolineareisomersofoctane.Astructuralformulaofoctaneisshownbelow.

Drawastructuralformulafor2,2,4-trimethylpentane.

Baseyouranswerstoquestions29 and30 ontheinformationbelow.

Manyestershavedistinctiveodors,whichleadtotheirwidespreaduseasartificialflavoringsandfragrances.Forexample,methylbutanoatehasanodorlikepineappleandethylmethanoatehasanodorlikeraspberry.

29. Whatisachemicalnameforthealcoholthatreactswithmethanoicacidtoproducetheesterthathasanodorlikeraspberry?

53

30. Drawastructuralformulafortheesterthathasanodorlikepineapple.

Baseyouranswerstoquestions31 through33 ontheequationbelow,whichrepresentsanorganiccompoundreactingwithbromine.

31. Whatisthegram-formulamassoftheproductinthisreaction?

32. Whattypeoforganicreactionisrepresentedbythisequation?

33. WhatistheIUPACnamefortheorganiccompoundthatreactswithBr2?

Baseyouranswerstoquestions34 through37 ontheinformationanddiagrambelowandonyourknowledgeofchemistry.

Crudeoilisamixtureofmanyhydrocarbonsthathavedifferentnumbersofcarbonatoms.Theuseofafractionatingtowerallowstheseparationofthismixturebasedontheboilingpointsofthehydrocarbons.Tobegintheseparationprocess,thecrudeoilisheatedtoabout400°Cinafurnace,causingmanyofthehydrocarbonsofthecrudeoiltovaporize.Thevaporizedmixtureispumpedintoafractionatingtowerthatisusuallymorethan30meterstall.Thetemperatureofthetowerishighestatthebottom.Asvaporizedsamplesofhydrocarbonstravelupthetower,theycoolandcondense.Theliquidhydrocarbonsarecollectedontraysandremovedfromthetower.Thediagrambelowillustratesthefractionaldistillationofthecrudeoilandthetemperaturerangesinwhichthedifferenthydrocarbonscondense.

34. Howmanyhydrogenatomsarepresentinonemoleculeofoctane?

35. WriteanIUPACnameofone saturatedhydrocarbonthatleavesthefractionatingtoweratless than40°C.

36. Describetherelationshipbetweenthestrengthoftheintermolecularforcesandthenumberofcarbonatomsinthedifferenthydrocarbonmolecules.

37. Statethetrendbetweentheboilingpointofthehydrocarbonscontainedinthecrudeoilandthenumberofcarbonatomsinthesemolecules.

Baseyouranswerstoquestions38 and39 ontheinformationbelow.Giventhereactionbetween1-buteneandchlorinegas:

C4H8 + Cl2 → C4H8Cl2

38. Drawthestructuralformulaoftheproduct1,2-dichlorobutane

39. Whichtypeofchemicalreactionisrepresentedbythisequation?

Baseyouranswerstoquestions40 and41 ontheinformationbelow.Diethyletheriswidelyusedasasolvent.

40. Drawthestructuralformulaforanalcoholthatisanisomerofdiethylether.

41. In the space provided draw the structural formula for diethyl ether.

42. Howisthebondingbetweencarbonatomsdifferentinunsaturatedhydrocarbonsandsaturatedhydrocarbons?

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