Chemistry 11

Organic Chemistry Unit Review

Name: Date: Block:

Answer the questions in the space provided.

1. Of the following molecules, choose 2 that best fit each description.

a) Structural Isomers a) ______________ , ____________

b) Unsaturated Hydrocarbons b) ______________ , ____________

c) Have the general formula CnH2n+2 c) ______________ , ____________

d) When water is added, forms an alcohol d) ______________ , ____________

e) Contain alkyl groups e) ______________ , ____________

2. Explain what is wrong with each of the following. If a given name is incorrect, provide the correct name.

a) 2-ethylheptane b) 5-methylhexane

c) d) 2-fluoro-4-hexyne

e)

CH3 C

CH3

CH3

CH3CH C CH2 CH3 CH3 CH2 CH2 CH CH3

CH3

CH2 CH CH2 CH3CH2 CH2

CH2CH2

CH3 CH2 CH CH CH3

A B C

D E

F G

H

2-butene pentane

CH3 CH2 CH CH3

CH3

F

CH3

CH3CH3

= 2,4,6-trimethylbenzene

1

sameformula A E F G DdiffarrangementB D F HA C E

unsaturatedhydrocarbonsB D F HA C

Tabrarch

incorrectlynumbered3 methyloctanelongestchainis NY 2 methylhexane8 not 7

X p triplebondneedstobelowest

extraHoncarbon 25 fluoro 2hexyre

incorrectlynumbered

1,3 5

3. Name the following molecules. a) b) c) d) e) f) g) h) i) j)

CH3CH2CH2

CH2 CH3

CH3 CH2 CH2 CH2 CH CH3CH2CH3

CH3 C CH2 C CH3

CH3

CH3

CH3

CH3

CH3 CH CH CH CH3

CH3

CH C CH2

CH3

CH3 C CH CH CH

BrCl

Cl

Br

I

CH3CH2

CH2

CH2

CH

CH2

CH2 CH3

Cl

Cl Cl

CH3 CH2 CH CH2 CH CH2 CH2 CH3

CH3 CH2CH3

CH3 CH2 CH2 CH2

C CCH2 CH3

H

H

6 5 4 30I 2

pentane 3 methylheptane

00 00I 2 3 4 56 n g

l 203405

5 ethyl 3 methyloctane 2,2 4,4 tetramethylpertone

I 2 3 45 I 2 3

O 4

4methyl 2 perter I butyeorbuty.ee

000 2I 23 4 56 3 IO O 4 5

3,4 dibromo 2,2 dichloro l ethylcyclopentane5 iodohexane

Z O43s n 6 5

00trans 3 octane 1,3 5 trichloroberzere

4. Draw the structures of the following compounds. a) 3-ethyl-4-methyloctane b) 3-heptyne c) 3,3-diethylpentane d) 3-chloro-1-ethylbenzene e) tetramethylbutane f) 1-chloro-3,4-dimethylcyclohexane g) 3-iodo-1-propyne h) dichloromethane i) 3-heptene j) cis-2-pentene

00

rem ran

O OOn rA Qc

2

t f

EIO

ELI H ti

the

5. Draw and name all of the structural isomers of C5H12. There are 3!

6. Draw and name as many structural isomers for C4H9OH. There are 4!

N pentane

2 methylbutane

2,2 dimethylpropane

0 l butanol

pH 2 butanol

o 2 methyl 1 propanol

Otbn

2 methyl 2 propanol

7. Match the following compounds to their appropriate descriptions.

1. _____ Ethanol

2. _____ A carboxylic acid

3. _____ A saturated hydrocarbon

4. _____ A ketone

5. _____ An aromatic ring

6. _____ popyne

7. _____ An ether

8. _____ An ester

9. _____ An aldehyde

10. _____ Benzene

11. _____ Alkane

12. _____ Alkene

13. _____ Alkyne

14. _____ Methanol

15. _____ C6H6

16. _____ C6H8

A B C

D E F

G H

C2H2 C2H4 C2H6

CH3 CH2 OH CH3 OH CH2 C OHNH2

O

CH2 C OHCH2

O

CH3

CH2 C CH2CH2

O

CH3 CH2 CH3

CH

O

I J

K L

M N

CH2 C OCH2

O

CH3 CH3CH2 O CH2CH2CH3 CH2 CH3

H C C C H

H

H

D HG F NC CI BN AM r EK NL J

8. Classify the following types of reactions as combustion, substitution, addition, elimination or polymerization:

a)

b)

c)

d)

e)

f)

g)

h)

SubstiNti on

Addition

Addi tion

subs titoti on

SobstiNtion

Poly weri cation

Additi on

EIin in akon

Extra Challenge!

1. Draw this molecule: 4,4,5-triethyl-2,3,5,6,8,8,-hexamethyl-6,7-dipropyldecane

2. Name the following compound:

CH

C C C C C C C CH3

CH

CH

CH2

CH3

CH3

FCl

Br

Cl

CH3

CH2

CH2

CH3

CH2

CH2

CH3

CH2

CH3

CH3

CH3

CH2

CH3

F

Br

Br

Br

F

or Uvinn1 IL s

l l 5 lo tetrabromo 2 3 dichloro 5,7 7 tie thylz g lo trifluoro 3 6 6 8 8 Peetamethyl 4 4 dipropyldecane

branches in alphaorder