d. 2-ethyl-3-propylcyclohexane e. 2-cyclobutylpentane 23. Name each aromatic hydrocarbon. a. CH CH C CH CH CH CH3 methylbenzene CH C C CH CH CH CH2 CH...
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d. 2-ethyl-3-propylcyclohexane
e. 2-cyclobutylpentane
23. Name each aromatic hydrocarbon. CH3 H2C
CH3
C
C
a.
HC
CH
HC
HC
CH
HC
CH C CH
CH
CH2 H2C
methylbenzene
CH3
c. 1-ethyl-3-propylbenzene
CH3
CH HC
CH
C HC
CH
HC
CH C
HC
C C
CH3
H3C
CH2 CH
b.
CH CH2
CH2 CH2
CH3
C HC
1,2,4-trimethylbenzene
CH
HC
d.
CH CH
2,5-diphenyloctane 24. Draw the condensed structural formula for each aromatic hydrocarbon. a. 1,3-diethyl-4-methyl-2-propylbenzene
b. 1,4-dimethylbenzene (historically known as para-xylene or p-xylene)
CH3
c. 1-ethyl-3-propylbenzene
d. 1,2-diethyl-4,5-dimethylbenzene
e. 2-phenyl-5-propyloctane
25. The molecule 2-methyl-5-ethylbenzene in named incorrectly. Draw the line structural formula for the molecule and name it correctly.
1-ethyl-4-methyl-benzene
26. Name each haloalkane. F
CH3
CH2 HC
a.
H3C
Cl
CH3
HC
Cl CH
2-fluorobutane
d.
Br CH2 C
b.
H3C
CH3
F
1,3-dichloro-2-fluorobutane CH2 CH3
3-bromo-3-methylpentane
CH H2C
e.
CH3
CH2 CH Br
1,3-dibromo-2-chlorocyclohexane
CH CH2
CH2
CH Cl
c.
CH2
Br CH
Cl
CH2
CH3
CH3
4-chloro-2-methylhexane
27. Draw the condensed structural formula for each haloalkane.
a. 1-iodopropane
b. 2-chloro-1-fluoroethane
c. 3-bromo-2,2-dimethylpentane
d. 1,4-dibromo-3-chlorohexane
e. 1,4-difluoro-3-propylcycloheptane
28. Identify any errors in the following names by drawing a line structure. Give the correct name for each haloalkane. a. 3-chlorobutane Cl
2-chlorobutane
b. 4-chloro-3-bromohexane Cl
3-bromo-4-chlorohexane
Br
c. 2,4-dichlorocyclopentane Cl
Cl
1,3-dichlorocyclopentane
d. 3-chloro-2,2-dimethylbutane Cl
3-chloro-2,2-dimethylbutane (no errors)
29. Name each alcohol OH CH2
a.
HC
H3C
c.
CH3
HO
propan-2-ol butan-2-ol HO
HO
OH
H3C
CH2
OH
CH2 C
CH HC
b.
CH2
CH3
d.
CH3
CH3
3-methylbutane-1,3-diol pentane-2,3-diol
30. Draw the complete structural diagram for each alcohol. a. ethanol
b. propan-1-ol
c. butane-1,2-diol
d. 3,4-dimethylhexan-2-ol
e. 2,3-diethylcyclohexanol
31. Name each of the following aldehydes. CH2
a.
H3C
O CH
CH3 CH
propanal
H2C CH3
b.
CH3
3-ethyl-4-methylhexanal
CH3 CH
O CH
H2C
c.
O HC
CH2 CH
CH2 H3C
H3C
Br CH
2-methylbutanal Br
CH2 CH CH
d.
O
2,4-dibromopentanal
32. Draw the condensed structural formula for each aldehyde. a. 3-methylbutanal
b. methanal (commonly known as formaldehyde)
c. 2-methylpropanal
d. 2-chloroethanal
e. 4,4-diethylhexanal
33. Explain why the following aldehydes are named incorrectly or cannot exist. a. 2-ethanal *no number for the ethanal b. 5-ethylhexanal *should be 5-methylheptanal
c. cyclobutanal *cyclo’s are always ketones (ending in –one)
d. 1-fluoropentanal *nothing wrong with this!!!
34. Name each of the following ketones. H3C
O
CH2
CH2 C
a.
H3C
O
CH3
butan-2-one c.
O H3C
C CH
b.
CH3 CH2
CH3
2-methylpentan-3-one
CH
CH2
C
CH
CH3
CH3
CH3
3-ethyl-4-methylhexan-2-one
35. Draw the line structural for each ketone. a. propanone (commonly known as acetone)
O
b. 3-ethylhexan-2-one
O
c. 4,4-diethylhexan-2,3-dione OH
OH
36. Explain why each ketone is named incorrectly or cannot exist. If it can exist, give the proper name. a. propan-1-one *should be propanal b. pentan-4-one *should be pentan-2-one c. 2-propylhexan-3,4-dione *should be 5-methyloctan-3,4-dione
d. benzene-1-one *impossible for a carbon to have 5 bonds (each carbon in benzene already has 3 bonds, there is not enough bonds to put a =O on it)
37. Name each carboxylic acid.
OH
O CH2 C
a.
H3C
CH3
C O
OH
propanoic acid
CH2 CH2
CH2 CH
H2C CH3
b. 4-ethylhexanoic acid
38. Draw the condensed structural formula for each carboxylic acid. a. butanoic acid (commonly known as butyric acid)
b. 4-ethyloctanoic acid
c. 3-methyl-4-phenylhexanoic acid
d. pentandioic acid (commonly known as glutaric acid)
39. Explain why each carboxylic acid is named incorrectly or cannot exist. If it can exist, give the proper name. a. hexan-6-oic acid
hexanoic acid
b. butan-2-oic acid Can’t exist (acid must be on carbon # 1)
c. 3-butylpentanoic acid
3-ethylheptanoic acid d. cyclohexanoic acid Can’t exist (the acid must be on the end of a chain)
40. Name each ester.
O H3C
O Cl
C O
CH
H3C
a.
c.
methyl ethanoate
CH
O
CH2 O
b.
C
H3C
ethyl methanoate
41. Draw the condensed structural formula of each ester. a. butyl ethanoate
b. ethyl butanoate
c. ethyl 2-cyclobutylpropanoate
CH2
O CH2 CH2
H3C
butyl 3-chlorobutanoate
CH2 CH3
42. Draw the line structure of the ester formed from each reaction. a. propanoic acid and ethanol O
O
b. butanoic acid and propanol
O
O
c. 3-fluoropentanoic acid and methanol
F
O
O
d. butanol and 4-phenylhexanoic acid
O
O
43. Name each ether. H3C
CH2
H3C
CH2 O CH2 CH3
a.
CH2 O
b.
CH2 CH
CH2
H2C
CH3 HC CH3
2-ethoxypropane
44. Draw the condensed structural formula for each ether. a. methoxyethane
CH2 CH2
c.
1-ethoxypropane
H3C
O CH2
ethoxycyclohexane
b. 2-propoxybutane
c. 3-ethoxy-4-methylhexane
d. 2-phenoxyheptane
45. Explain why each ether is named incorrectly or cannot exist. If it can exist, give the correct name. a. ethoxymethane Should be methoxyethane b. 3-propoxybutane Should be 2-propoxybutane (number the butane from the other end)
c. 4-methoxy-4-methylbutane Should be 2-methoxypentane
d. 2-ethoxybenzene Should be ethoxybenzene
46. Name each amine. H3C
CH2
H3C
CH2 CH2
CH2 CH2 CH
CH2 NH2
a.
NH
H3C
c.
CH2 CH3
CH3 H3C
H3C
CH2 H2C
CH2 CH
b.
NH2
CH2 CH2
CH2 HC
CH2 CH2
CH2
CH3
N
d.
47. Draw the condensed structural formula for each amine. a. methanamine
H3C
CH2 CH2 CH3
