12 U Organic Chemistry Worksheet # 3 – Organic Functional Group Nomenclature
1. Draw the following alcohols
a) heptan-2-ol
b) 3-methylhexan-1-ol
c) cyclopropanol
d) 2,4,6-trichlorooctan-2-ol
e) pentan-1,4-diol
f) benzene-1,3-diol
g) but-2-ene-1-ol
h) 4-methylpent-2-yne-1-ol
i) 3,4-dimethylcycloheptan-1-ol
2. Name the following alcohols
H3C
CH2
a) H3C
CH2
CH2
CH2
CH
OH
CH2
CH2
CH2
CH
CH
OH
b)
CH3
CH3
c) HO
OH
Cl
CH2
OH
H3C
CH2
CH2
CH
CH
CH2
CH2
CH
HC
OH
CH
CH3
CH3
CH2
e)
CH2
OH
H2C
d)
CH3
f) CH2
OH
C
HC
CH
HC
CH
CH2
CH3
H3C
CH2 HC
h) H3C
CH
g)
C
CH2
C
OH
CH3
CH3
C
C
CH3
CH3
OH
HC
CH2
CH2
CH3
i)
3. Explain why the propane that is used as a fuel in a BBQ is gas at room temperature, but 2-propanol used as
rubbing alcohol is a liquid at room temperature.
4. Draw the following ethers
a) 1-propoxypentane
b) 2-ethoxybutane
c) 1-methoxy-4-chlorohexane
d) 3-butoxy-2,4-dimethyloctane
e) 2-propoxy-4-phenylheptane
f) 1-ethoxycyclopentane
5. Name the following ethers
CH3
CH
H3C
O
CH3
CH
CH
CH2
a) H3C
O
CH2
H3C
CH3
CH2
b)
CH2
CH
CH3
CH3
H2C
O
c)
CH3
CH2
CH2
CH3
H3C
CH3
CH2 CH3
H3C
HC
CH2
O
H3C
CH2
CH2
CH2
O
CH2 O
CH CH2
CH2
CH2
CH3
H2C
CH
CH2
CH2 CH3
d)
CH2
CH3
e)
H3C
f)
6. Why is ether no longer used as an anesthetic? Explain using your knowledge of its state and structure.
7. Draw the following aldehydes and ketones
a) hexanal
b) heptan-3-one
c) 3-methyloctanal
d) 2,2-dimethylhexan-3-one
e) 2,4,6-trichloroheptanal
f) 4-phenyloctan-2-one
g) 2-methylcyclohexanone
h) 4-hydroxyhexanal
i) penta-1,4-dione
8. Name the following aldehydes and ketones
H3C
H3C
CH2
O
CH3
CH
C
CH2
CH2
a)
b) H3C
O
CH2
CH2
H3C
CH
CH2
O
C
CH3
HC
CH2 HC
CH3
c)
CH3
CH3
H2C
C
O
H3C
CH2
CH3
CH
H3C
CH
O
CH3
Cl
CH HC
H2C
C
e) O
O
d)
CH
CH2
CH
CH3
f)
CH3
g)
C
CH
CH3
Br
9. Explain why no numeral is needed as a prefix in the naming of butanal and butanone.
10. Arrange the following compounds in increasing order of predicted solubility, and give reasons for your answers:
butanal, butane, butanol.
11. Draw the following carboxylic acids
a) butanoic acid
b) 2-methylpentanoic acid
c) 3,5-dimethylheptanoic acid
d) 5-hydroxyhexanoic acid
e) 2,3,4-trichlorobutanoic acid
f) 2-bromoethanoic acid
12. Name the following carboxylic acids
H3C
OH
CH2
a) H3C
CH2
CH2
H3C
C
CH2
CH2
CH3
O
b)
C
CH3
OH
O
C
CH
OH
c) HO
CH2
CH2
C
CH2
O
HO
CH3
C
CH2
O
F
H3C
H3C
HC
O
CH
CH2
C
C
F
d)
O
OH
C
H3C
CH3
C
CH2
CH3
OH
e)
CH2
f)
13. The labels have fallen off three bottles. Bottle A contains a gas, bottle B contains a liquid, and bottle C contains
a solid. The labels indicate that the compounds have the same number of carbon atoms, one being an alkane, one
an alcohol, and the other a carboxylic acid. Suggest the identity of the contents of each bottle, and give reasons for
your explanation.
14. Draw the following esters
a) ethyl butanoate
b) pentyl propanoate
c) propyl 3-ethylhexanoate
d) methyl 4-phenylpentanoate
e) 2,3-dimethylpentyl ethanoate
f) butyl 3-hydroxyheptanoate
15. Name the following esters
O
O
CH2
C
H3C
CH2
CH2
O
CH3
a)
H3C
CH2
CH2
O
CH2
H3C
CH2
CH3
O
O
C
C
O
O
C
CH3
CH3 CH3
d)
O
CH2
e) H3C
CH2
CH2
C
H3C
CH2
CH2
O
CH3
OH
c)
CH3 CH3
C
C
CH
C
b)
O
H3C
O
C
CH2
CH3
CH2
CH2
CH3
CH3
CH3 f)
16. In what way is the functional group of an ester different from that of a carboxylic acid? How does this difference
account for any differences in properties?
17. Describe the steps used to name an ester.
18. Draw the following amines
a) butan-1-amine
b) pentan-2-amine
c) propan-1,2-diamine
d) N-ethyl-hexan-2-amine
e) N,N-dimethyl-pentan-3-amine
f) N-methyl-N-propyl-ethanamine
19. Name the following amines
H3C
H3C
a)
CH3
CH3
CH
CH
CH
NH2
CH3
CH2
H2C
H2C
Cl
Cl
CH2
CH2
CH
CH3
b)
NH2
CH2
CH HC
c)
H2N
NH2
CH2
H3C
CH3
CH
d) H2N
CH2
CH2
CH3
CH
CH2
N
NH2
CH2
H3C
e)
CH3
f) H3C
NH
CH2
CH3
CH2
20. Explain why amines generally have lower boiling points than alcohols of comparable molar mass.
21. Why are secondary and tertiary amines less soluble than primary amines of similar molecular size?
22. In some cuisines, fish recipes include lemon garnish or a vinegar sauce such as sweet and sour sauce. Suggest
a reason why these common culinary techniques might be used.
23. Draw the following amides
a) N-ethylbutanamide
b) N-propylpentanamide
c) N-methyl-3-methylhexanamide
d) N-2,3-dichlorobutylpropanamide
e) N,N-diethyl-2-methylbutanamide
f) N-pentyl-3-hydroxypentanamide
24. Name the following amides
O
O
CH2
H3C
CH2
a) H3C
C
CH2
CH2
NH
C
CH2
CH3
H3C
N
C
CH3
CH2
H3C
CH3
b)
CH2
NH
CH2
C
CH3
c)
O
CH3
O
O
H3C
H3C
CH2
d) H3C
CH2
CH2
C
CH2
C
NH
CH2
CH
N
CH3
CH3
CH2 HC
CH3
CH2
CH2
CH
NH
O e)
f)
25. Describe the steps used to name an amide.
26. Which functional groups can you expect to turn litmus paper red? Blue?
27. Which functional groups would form hydrogen bonds with neighbouring molecules?
28. Draw as many structural isomers with the formula C4H10O as possible.
Cl
CH3