CHEM 1152 - Chem Workbook

7/27/2019 CHEM 1152 - Chem Workbook

1/48


2/48

2SCH4U0 CHEMISTRY Workbook

Page 2 of48


3/48


Page 3 of48


4/48


Page 4 of48


5/48


PREPARATION OF ALKANES

1. Hydrogenation of alkenesH2

Pt

2. Hydrogenation of alkynes

H2

PtCH CH CH3 CH3

2

REACTION OF ALKANES

1. Halogenation

CH3 H + X2light

CH3 X

Reactivity: X2: Cl2 > Br2

H: 3>2>1>CH3-H

PREPARATION OF ALKYL HALIDES

1. From Alcohols

CH3 OH CH3 XHX or PX3

X = Cl, Br, or I

2. Halogenation of certain hydrocarbons

CH3 H + X2light

CH3 X

Reactivity: X2: Cl2 > Br2

H: 3>2>1>CH3-H

3. Addition of hydrogen halides to akenes

CH2 CH2HX

X H

H

H

H

H

H usually attaches to least substituted carbon atom in double bond (Markovnikov addition)

4. Addition of halogens to alkenes or alkynes

CH2 CH2X X

HH

H

H

X2CH CH

X22XX

X X

HH

Page 5 of48


6/48


trans-addition across double bonds in rings

5. Halide exchange

CH3 X + NaI (or NaBr) CH3 I(or Br) + NaClacetone

X=Cl or Br

1>>2

NaCl ppts from acetone and drive the reaction to completion

REACTION OF ALKYL HALIDES

1. Nucleophile Substitution

CH3 X + OH- CH3 OH alcohol

+ H2O CH3 OH alcohol

+ C R CH3 R alkyne

+ R M CH3 R alkane couplingM = Li or Mg

+ I- CH3 I alkyl iodide

+ RCOO- CH3O

ORester

+ NH3 CH3 NH2 primary amineNH2R

NHR'R"

secondary amine

tertiary amine

2. Dehydrohalogenation: Elimation

H X

H

H

H

Hbase

CH2 CH2

3. Preparation of Grignard Reagent

CH3 X Mg+ether

CH3 MgX

PREPARATION OF ALCOHOLS

1. Hydration

CH2 CH2 + H2OOHH

H

H

H

H

Markovnikov addition

2. Grignard synthesis

CH3 CH3

O

+ R-Mg-X ether

CH3

CH3

R

OMgX H2O

R

CH3

CH3

OH

Page 6 of48


7/48


Ketones or aldehydes

3. Hydrolysis of alkyl halides

CH3 X + OH- CH3 OH + X-

Usually requires a silver salt so can be very expensive

4. Reduction of ketones and aldehydes

CH3 H

OH2, Pt

CH3 H

OHH

CH3 CH3

OH2, Pt

CH3 CH3

OH

H

5. Hydrolysis of alkenes

CH2 CH2

KMnO4

OHOH

HHH

Hcis-addition

6. Hydrolysis of Esters

CH3

O

OR

H+

or

NaOH, H2O CH3

O

OH

+ OH R

REACTION OF ALCOHOLS

1. Reaction with hydrogen halides

CH3 OH + HX CH3 X

2. Dehydration

OHH

H

H

H

HH

+

CH2 CH2heat

More substituted alkenes is favoured: 3>2>1

3. Ester Formation

CH3OH

O

+ R OH H+

CH3

O

OR

4. Oxidation

Page 7 of48


8/48


CH3 OHPCC, CH2Cl2

CH3H

O

CH3 CH3

OH

H

KMnO4

CH3

CH3

O

excess, KMnO4

CH3 OH

O

PREPARATION OF ETHERS

1. Condensation

CH3 OH OH R+ CH3 OR

PREPARATION OF ALKENES

1. Reduction of Alkynes

CH CH

H21

PtCH2 CH2

REACTION OF ALKENES

1. Addition of hydrogen. Catalytic hydrogenation

CH2 CH2

H2, Pt

CH3 CH3

2. Addition of halogens

CH2 CH2

X2

X X

HHH

H

3. addition of hydrogen halides

CH3

CH2

HXCH3

CH3

X

Markovnikov addition

4. addition of water

CH3

CH2

OH2CH3

CH3

OH

H+

Markovnikovs addition

5. Hydroxylation

CH2 CH2

KMnO4

OH OH

HHH

H

PREPARATION OF ALKYNES

Page 8 of48


9/48


1. Reaction of metal acetylides with primary alkyl halides

CH3

CH

Na

CH3

C- Na+

R X

R must be primary

CH3

R

REACTION OF ALKYNES

1. Addition of hydrogenCH CH

1 H2, PtCH2 CH2

1 H2, PtCH3 CH3

2. Addition of halogens

CH CH2 X2

X

X X

XH H

3. Addition of hydrogen halides

CHCH3

2 HX

CH3

X

H

X

H Markovnikov Addition

4. Formation of metal acetylides

CH3

CH

Na

CH3

C- Na+

PREPARATION OF ALDEHYDES

1. Oxidation of primary alcohols

OH

CH3

KMnO4CH3

O

H

PREPARATION OF KETONES

1. Oxidation of secondary alcohols

CH3

CH3

OHKMnO4

CH3CH3

O

REACTION OF ALDEHYDES and KETONES

1. Oxidation of aldehydes carboxylic acid

CH3

O

H

KMnO4

CH3

O

OH

2. Reduction of aldehydes 1 alcohols

Page 9 of48


10/48


CH3

O

H

H2, Pt

CH3

OH

H

H

3. Reduction of ketones 2 alcohol

CH3 CH3

O

H2, PtCH

3 CH3

OH H

PREPARATION OF CARBOXYLIC ACIDS

1. Oxidation of primary alcohols

OHCH3

KMnO4, excessCH3

O

OH

2. Hydrolysis of Esters

CH3

O

OR

H+

or

NaOH, H2O CH3

O

OH + OHR

REACTIONS OF CARBOXYLIC ACIDS

1. Acidity. Salt Formation

CH3 OH

O+

NaOHCH3

O-

O

Na+

2. Conversion into Ester

CH3OH

O

+ R OH H+

CH3

O

OR

3. Conversion into Amide

CH3OH

O

CH3NH2+ CH3 NH

O

CH3

REACTION OF BENZENE

HNO3

H2SO4

NO2CH3CH3

Cl

AlCl3

Page 10 of48


11/48


Intramolecular and Intermolecular Forces

Intramolecular forces

Forces of electrostatic attraction within a molecule

Occur between the nuclei of the atoms and their electrons making up the molecule (i.e. covalent bonds)

Must be broken by chemical means

Form new substances when broken

Intermolecular forces

Forces of attraction between two molecules (i.e. London dispersion forces, dipole dipole interactions orhydrogen bonds)

These forces are much weaker than Intramolecular forces or bonds and are much easier to break

Physical changes ( changes of state) break or weaken these forces

Do not form new substances when broken

These forces affect the melting and boiling points of substances, the capillary action and surface tension, aswell as the volatility and solubility of substances

Types of Intermolecular forces

London dispersion forces

These forces are based on the simultaneous attraction of the electrons of one molecule by the positive nucleiof neighbouring molecules

The strength of the force is directly related to the number of electrons and protons in a given molecule

The greater the number of electrons and protons the greater the forceDipole - Dipole Interactions

Occur between polar molecules having dipoles

Molecules with dipoles are characterized by oppositely charged ends that are due to an unequal distribution ofcharge on the molecule

The polarity of a molecule is determined by both the polarity of the Intramolecular bond and the shape of themolecule

These forces are based on the simultaneous attraction of the electrons of one dipole by the dipoles ofneighbouring molecules

The strength of the force is related to the polarity of the given moleculeHydrogen Bonds

These forces are a type of dipole dipole interaction

Occur between Hydrogen atoms in one molecule and highly electronegative atoms [F, O, N, and S, P] where

there are usually unshared pairs of electrons present Hydrogen bond are the strongest of the Intramolecular forces and are about 1/10 the strength of a covalent

bond

Polarity and Boiling Point:

The polarity of the molecules determines the forces of attraction between the molecules in the liquid

state. Polar molecules are attracted by the opposite charge effect (the positive end of one molecule is

Page 11 of48


12/48


attracted to the negative end of another molecule. Molecules have different degrees of polarity asdetermined by the functional group present.

Principle: The greater the forces of attraction the higher the boiling point or the greater the

polarity the higher the boiling point.

Molecules that are isoelectronic have the same strength of London dispersion forces

More polar molecules have stronger dipole dipole interaction and higher melting and boiling points The greater the number of electrons per molecule, the stronger the London forces and hence the higher

the melting and boiling point

Polarity Ranking of the Functional Groups:(most polar first)

Amide > Acid > Alcohol > Ketone ~ Aldehyde > Amine > Ester > Ether > Alkane

HW: Review of INTERMOLECULAR FORCES

2-13 For each of the following:

1. Record EN above each element2. EN difference predict type bond (polar covalent vs. non-polar covalent)3. SHOW presence of Dipole MOMENT (if any) Example:

H

H

Cl

Cl

H

H

H

F

F

F

F

F

H

O CH32.2

3.44 2.55

H

O

CH3 H

N

H

H

N

CH3CH3

CH3

HH

HCl

B

H

HH

Be ClCl

N+

H

H

H

H

Rank the following compounds in order of increasing boiling points. Explain the reason.

Page 12 of48


13/48


CH3CH3

octane

CH3

CH3

CH3

CH3

CH3OH

butan-1-ol

2,3-dimethylbutane

CH3

CH3

OH

CH3

2-methylbutan-2-ol

2-16 For each pair of compounds circle the compound you expect to have the higher

boiling point. Explain your reasoning.

a) (CH3)3C-C(CH3)3 and (CH3)2CH-CH2CH2-CH(CH3)2

b) CH3(CH2)6CH3and CH3(CH2)5CH2OH

c) HOCH2-(CH2)4-CH2OH and (CH3)3CCH(OH)CH3

d) (CH3CH2CH2)2NH and (CH3CH2)3N

CH3

CH3

CH3

CH3

CH3CH3

CH3

CH3H

CH3

CH3

H

H

H

HH

CH3

H

HH

CH3OH

HH

OHOH

HH

H H

CH3

CH3CH3

H OH

CH3CH3

N

CH3

H

CH3

N

CH3

CH3

a)b)

c)

d)

2-17 Circle the member of each pair that is more soluble in water. Show the molecular

Page 13 of48

ANSWER


14/48


representation

a) CH3CH2-O-CH2CH3 or CH3CH2CH2CH2CH3

b) CH3CH2NHCH3 or CH3CH2CH2CH3

c) CH3CH2OH or CH3CH2CH2CH2OH

CH3O CH3

CH3CH3

a)

CH3N

CH3

H

CH3 CH3

b)

CH3OH

CH3

OH

HH

c)

Page 14 of48


15/48


Page 15 of48

ACTIVITY 1.2 THOUGHT LAB


16/48


Page 16 of48


17/48


Name Number of C atoms Molecular Formula

Methane 1 CH4

Ethane 2 C2H6

Propane 3 C3H8

Butane 4 C4H10

Pentane 5 C5H12

Hexane 6 C6H14

Heptane 7 C7H16

Octane 8 C8H18

Nonane 9 C9H20

Decane 10 C10H22

Naming ORGANIC COMPOUNDS Find the longest continuous carbon chain. Determine the root name for thisparent chain. In cyclic compounds, the ring is

usually considered the parent chain, unless it isattached to a longer chain of carbons; indicate a ring with the prefix cyclobefore the rootname. (When there are two longest chains of equal length, use the chain with the greater numberofsubstituents.).

Number the chain in the direction such that the position number of the firstsubstituent is the smaller number. If the firstsubstituents from either end have the same number,then number so that the second substituent has the smaller number, etc.

Determine the name and position number of each substituent. (A substituent ona nitrogen is designated with an N insteadof a number)

Indicate the number of identical groups by the prefixes di, tri, tetra, etc.

Place the position numbers and names of the substituent groups, in alphabetical order, before the root name. Inalphabetizing, ignore prefixes likesec-, tert-, di, tri, etc., butinclude iso and cyclo. Always include a position number foreach substituent, regardless ofredundancies.

Page 17 of48


18/48


Worksheet #2

Page 18 of48


19/48


Worksheet #3 - QUESTIONS: naming alkanes and cycloalkanesPractice Problems: name the following alkenes from their condensed structural formulas.

Page 19 of48


20/48


Page 20 of48

STRUCTURE NAME STRUCTURE NAME

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

3-ethyl-3,4-

dimethylhexane

Hexane

3-ethyl-2,5-

dimethylheptane

3-methyl-2-

isopropyloctane

4-tert-butyl-3,8-

dimethyldecane

2,7-dimethyl-4,5-

dipropyloctane

CH3 CH3

CH3

CH3

CH3

1-isopropyl-3-

methylcyclopentane

CH3

CH3

CH3 1-ethyl-2,4-

dimethylcyclohexane

1-chloro-3-

ethylcyclooctane

cyclopropylcyclohexane

2,3,4-trimethylpentane 3,4-dichloro-2-


21/48


Worksheet #4 - naming alkenes, cycloalkenes, alkynesNaming Alkenes and Alkynes The naming of alkenes is very similar to the naming of alkanes, with two exceptions.

In alkenes the double bonds take precedence over the substituted groups

The chain is numbered so that the double bonds have the lowest location numbers possible. If the double

bonds do not indicate a preferred numbering direction, look then to substituted atom

If more than one double bond is present, give the position of each and use one of the suffixes diene,-triene, and so on

For a cycloalkene, the double bond must be numbered 1,2

Note the double bond must be included in your longest chain.

Because of restricted rotation about a C=C double bond, groups on adjacent carbons are eithercis or

trans to each other

The cis-trans system: configuration is determined by the orientation of atoms of the main chain

We use the terms cis and trans to distinguish between alkenes which have identical groups on either side

of the double bond

NOTE: (alkene and alkyne) are considered to have equal priority: in a moleculewith both a double and a triple bond, whichever is closer to the end of the chaindetermines the direction of numbering. In the case where each would have the sameposition number, the double bond takes the lower number. In the name, ene comes

before yne because of alphabetization.

Page 21 of48


22/48


Page 22 of48

STRUCTURE NAME STRUCTURE NAMECH3

CH2 CH3CH2

CH3

CH3

CH3

CH

CH3CH3

CH3

CH3

CH3

CH3

CH3

CH2

CH3

CH3

CH3

CH3

CH3

CH3 CH3

CH3CH3

CH3

Cl

CH3

CH3CH3

CH3 CH3

4-ethylcyclopentene CH3

CH3

CH3

CH3

CH3 2-isopropyl-4-

methylpenta-1,3-diene

cis-2,4,6-octatriene 2,5-dimethylhex-3-yne

1,3-dimethylcyclopenta-

1,3-diene

2-methylpent-1-ene

3,4-dimethylpent-1-yne

CH3

CH3

CH3

CH3

2,4-methylhex-2-ene 4-chloro-1-

cyclopentyl-2-

methyl-1,3-

cycloheptadiene4-methylhept-1-ene 2,4-methylhex-2-ene


23/48


Page 23 of48


24/48


Organic Chemistry Nomenclature Project

Hydrocarbons

CH3 CH3

CH3CH3

cyclopentane

1)____________________________ 2)__________________________________

CH3CH3CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

3)____________________________ 4)__________________________________

5-butyl-3,3,7,7-tetramethylnonane 2,3-dimethylbutane

5)____________________________ 6)__________________________________

dimethylcyclopropyne 5-cyclopropyl-trans-3-heptene

7)____________________________ 8)__________________________________

CH3

CH3

4-butyl-2-ethyl-1-pentyl-1,4-cycloheptadiene

9)____________________________ 10)__________________________________

Page 24 of48


25/48


Name: Page 2

Page 25 of48


26/48



Aromatics

CH3CH3

3-phenylpentane

1)____________________________ 2)__________________________________

methyldiphenylmethane p cyclopropylethylbenzene3)____________________________ 4)__________________________________

CH3

CH3

5-butyl-3-ethyl-7-phenylnonane

5)____________________________ 6)__________________________________

NO2O2N

CH3

CH3 7)____________________________ 8)__________________________________

CH3CH

3

2,4-dimethyl-1-propylbenzene

9)____________________________ 10)__________________________________

Name: Page 3

Page 26 of48


27/48



Halides

CH3

Br

Cl

F

CH3 o 1,3-dichlorobenzene

1)____________________________ 2)__________________________________

3-bromo-2,4,4-trifluoro-6-iodoheptane 1,2,3,4,8-pentaiodo-1,3,5-cyclooctatriene3)____________________________ 4)__________________________________

Br

Br

CH3 CH3

NO2

Cl

5)____________________________ 6)__________________________________

Cl

FBr

F

6-chloro-1,1,1-trifluoro-2-phenyl-3-heptyne

7)____________________________ 8)__________________________________

ClF

I

Br

CH3

4,7,9-tribromo-3-fluoro-6,8-dimethyl-cis-2-decene

9)____________________________ 10)__________________________________

Page 27 of48


28/48


Worksheet #8: REACTIONS OF HYDROCARBONS

1)

2) PREDICT PRODUCTS:

ADVANCED:

Page 28 of48


29/48


ADVANCED

ADVANCED

3) For each of following reactions use structural diagram to show all reactants and products. Be sure to include al

names, reaction conditions and catalysts.a. 3-ethyl-2-heptene reacts with water in the presence of acidb. 2-methyl-2-pentene reacts with hydrochloric acidc. tertiary-butane reacts with bromine gas in the presence of lightd. halogenation of propanee. bromomethane is purged with NaIf. hydrogenation of 1,3-dimethylcyclopenta-1,3-dieneg. Hydration of 2-isopropyl-4-methylpenta-1,3-dieneh. Complete hydrohalogenation of 2,5-dimethylhex-3-ynei. Combustion (extreme oxidation) ofcis-2,4,6-octatrienej. Complete halogenation of 3-methylhept-1-ynek. Octane burns in oxygenl. 2-methylcyclohex-1-ene reacts with hydrobromic acid

4) Predict the products of each of the following reactions. (Name the reactants and products).

5) Synthesis the following molecules.

5)Explainwhy it isthat acidcatalyzedaddition ofwater to 1-

methylcyclobutene gives 1-methylcyclobutanol and not 2-methylcyclobutanol.

Page 29 of48


30/48


Worksheet #9: Naming, Reactions, synthesis of Alcohols and Ethers

1. Indicate whether the following alcohols are primary, secondary, or tertiary.

a)CH3

OH

b)

CH3

CH3

CH3

OH

c)

CH3

OH

d)

OH e)2-methyl-2-pentanol

f)CH3

OH

2. Diethyl ether (commonly called ether) is a structural isomer of 1-butanol. Whichcompound would you expect to have the higher boiling point? Explain your answer.

3. For each of the following pairs of compounds give a simple, visual chemical test you coulduse to distinguish between the two molecules. Give chemical reagents and theobservation you would make.

a)CH3 OH

and

CH3 O

CH3

b)CH3

OH and

CH3

CH3

CH3

OH

c)

OH

and OH

4) Give the products of the following reactions. Use N.R. if no reaction occurs

a)CH3

OHHCl

b)CH3

CH3

OH

+ K2Cr2O7H+

c)CH3

OH+conc.H2SO4

Page 30 of48


31/48


e)+CH3O

-Na+ CH3Br

f)CH3 OH + KMnO4 (excess)

g)+

OH

PCC/CH2Cl

2

H+

h)CH3

CH3

I

+ dilute NaOH25C

5) For each of the following, provide the reagent(s) required to convert the starting

compounds into the products. Some of these conversions may required more than a single

reaction step.

a)

CH3OH

CH3

b)CH3 CH3

CH3 CH3

O

2 steps

c)CH3

BrCH3

OH

d)

OH

2 steps

e)

CH3 OHCH3

O

OH

f)

BrO

2 steps

Name or draw structures for the following compounds.

(e) isobutyl alcohol(f) 2-buten-1-ol(g) 2,4-hexanediol(h) cis-3-ethylcyclobutanol

Name: Page B4Page 31 of48


32/48



Alcohols

OH

CH3CH3

2-bromo-3,4-dihydroxypentane

1)____________________________ 2)__________________________________

OH

2-hydroxy-1,3-cyclobutadiene

3)____________________________ 4)__________________________________

ICl Cl

OHOHCl

CH3CH3

4-hydroxy-trans-2-hexane

5)____________________________ 6)__________________________________

OH

OH

p1,2-dihydroxybenzene

7)____________________________ 8)__________________________________

OH

CH3

CH3

CH3

CH3

CH3

3,4,4-triphenyl-2-butanol

9)____________________________ 10)__________________________________

Page 32 of48


33/48


Name: Page B5


Ethers

CH3 O

CH3

4-methoxy-2-pentyne

1)____________________________ 2)__________________________________

O

OH

CH3

2-chloroxypropane3)____________________________ 4)__________________________________

CH3 O

CH3 O O

dipropylether

5)____________________________ 6)__________________________________

O

CH3

CH3

2,6-dibromo-5-fluoroxy-4-methyl-cis-2-heptene

7)____________________________ 8)__________________________________

O

3-iodo-3-methoxy-2-phenyl-1-propanol

9)____________________________ 10)__________________________________

Page 33 of48


34/48


Worksheet #10

Naming, Synthesis, Reactions of Aldehydes, Ketones, Carboxylic

Acids

Page 34 of48


35/48


PRACTICE: Name the following compounds

1.

2.

3

4

5

6

7

8

9

10Give the products of the following reactions. Use N.R. if no reaction occurs.

a)

CH3O

H

H2

Pt

Page 35 of48


36/48


b)

CH3O

H

KMnO4, H+

c)

CH3

CH

CH3

Na+

+

O

ClH

d) CH3CH3

O K2Cr

2O

7, H+

e) CH3 OH

O

OH2+

f)CH3

OH

O

+Na OH

g)CH3

O

H

K2Cr

2O

7, H+

Page 36 of48


37/48


Name: Page B6


Aldehydes and Ketones

CH3

O

CH3 propanal

1)____________________________ 2)__________________________________

O

CH3

CH3

CH3

2,4-dichlorobenzaldehyde

3)____________________________ 4)__________________________________

CH3

OO

CH3

CH3

4-cyclobutyl-trans-2-pentenal

5)_____________________________ 6)__________________________________

O

CH2

2,6-difluoro-3,3,5-trihydroxycyclooctanone

7)___________________________ 8)__________________________________

Page 37 of48


38/48


pent-4-yn-2-one 4-chloroxy-1,2-dibromo-2-methyl-4-nitro-butanal

9)____________________________ 10)__________________________________

Name: Page B7

Organic Chemistry Nomenclature ProjectCarboxylic Acids

OHOH

O

OH

CH3

pentanoic acid

1)____________________________ 2)__________________________________

CH3

CH3

CH3

CH3

CH3

O

OHCH3

2,5-dimethyl-cis-3-heptenoic acid

3)____________________________ 4)__________________________________

CH3

O

OH

4-cyclopropyl-2-nitro-3-butynoic acid

5)____________________________ 6)__________________________________

CHO

OH

CH33-methoxybenzoic acid

7)____________________________ 8)__________________________________

I

I

O

CH3

O

OH

CH3

Page 38 of48


39/48


butanedioic acid

9)____________________________ 10)__________________________________

Page 39 of48


40/48


Page 40 of48


41/48


Name: Page B8


Esters

CH3

O

O

CH3

propyl butanoate

1)____________________________ 2)__________________________________

Page 41 of48


42/48


phenyl hexanoate dichloromethyl 2-ethoxypropanoate

3)____________________________ 4)__________________________________

CH3

Br O

O

CH3

CH3

methyl acetate

5)____________________________ 6)__________________________________

2-phenyl-trans-3-pentenyl 2-hydroxybenzoate 2-nitrocyclohexyl ethanoate

7)____________________________ 8)__________________________________

CH3

CH3

O

O CH3 O

O

O

CH3CH3

9)____________________________ 10)__________________________________

Page 42 of48


43/48


Name: Page B9


Amines

CH3

CH3

NCH3

ethylmethylamine

1)____________________________ 2)__________________________________

OHNH

CH3

CH33-amino-4,5,6,7-tetramethylnonane

3)____________________________ 4)__________________________________

2,3-diamino-N3-chloro-N2-methylpentane cyclopentyl 2-amino-N-methylbutanoate

5)____________________________ 6)__________________________________

N

5-aminohex-1-yn-3-one

7)____________________________ 8)__________________________________

CH3

OH

NH2

NH

CH3

N,N-dimethylaniline9)____________________________ 10)_________________________________

Page 43 of48


44/48


Name: Page B10


Amides

CH3O

NH2

2-bromo-N-ethylpropanamide

1)____________________________ 2)__________________________________

CH3

NH2

F

CH3 O

N

3-cyclopropyloxy-N-ethyl-N,6-dimethylheptanamide

3)____________________________ 4)__________________________________

NH

CH3 O

NO2

N-iodo-N-methyl-3-pentynamide 5)____________________________ 6)__________________________________

OBrBr

CH3

O NH2 CH3

N-cycloheptyl-N-phenylacetamide

7)____________________________ 8)__________________________________

CH3

OH

CH3

O

CH3O

CH3 O

NH2

N,N-dihydroxybenzamide

9)____________________________ 10)__________________________________

Page 44 of48


45/48


Page 45 of48

Worksheet #11


46/48


Page 46 of48


47/48


Worksheet #12 REVIEW

1. Write structural formulas for all organic compounds. State the type of reaction. Complete and balance the reaction. Name the

products.

a) propene + hydrogen

b) cyclohexane + chlorine

c) benzene + iodine

d) ethanol + butanoic acid

e) 2-pentene + bromine

f) ethene + water

g) chloroethane + sodium hydroxide

h) propene + bromine

i) chlorobenzene + chlorine

j) ethanol + hexanoic acid

k) 3-pentanol + oxygen

l) propyne + (2 mol) iodine

m) cyclohexene + water

n) ethoxyhexane + oxygen

o) polymerization of chloroethene

p) polymerization of propene

2. Account for the variation in boiling points among the following two carbon molecules:

ethane -88.6C chloroethane 12.2C

ethanol 78.5C ethanoic acid 117.9C

3. Draw structural formulas for each of the following molecules. Predict and explain the order of their boiling points

from highest to lowest.

a) CH3F b) C2H6 c) CH3OH d) C2H4

4. Given one of the starting materials and end product for each of the following reactions, show all reactants, reaction

conditions in brackets (where known) and products.

1. fluoroethane from ethanol

2. 3-methylpentane from 3-methyl-3-pentanol

3. acetone from propene

4. acetic acid from chloroethane

5. 2-iodopropane from acetone

6. 1-butanol reacts in the presence of concentrated sulfuric acid

7. ethyl ethanoate from ethane

8. isopropylbenzene from benzene

Page 47 of48


48/48


5. Draw the following hydrocarbons. Make sure you know how to do line diagrams,

condensed formulas and structural formulas.

1. dichloromethane 2. 3,5-dichloro-4-cyclobutylheptane

3. cis-2,4,6-octatriene 4. 4-chloro-1-cyclopentyl-2-methyl-1,3-

cycloheptadiene

5. cyclohexylcyclohexane 6. 3-ethyl-5,5-diisopropyl-2-methyloctane

7. 2-methyl-4nitroocta-2-ene-5-yne 8. 5-chloro-3-ethyl-1-nitro-1,4-cyclooctadiene

9. trans-2,3-dichloro-6-isopropyl-4,5,7-trimethyl-2,4,6-decatriene

10. 1,2-dibromo-3,8-dichloro-5-ethyl-4-nitrooctacis-1-trans-3,7-triene-5-yne

Name the following hydrocarbons.

3. 4.

5. 6.

7. 8.

Cl Cl

H3C

HC

CH

HC

CH

CH3

CH3CH2C(CH3)2CH2CH3CH3(CH2)6CHCH2

Cl NH2

C C C C C C C

H

Cl

H

Cl Cl

H

H

H

HH

Br

CHEM 1152 - Chem Workbook

Documents