Problem 60
Question
Draw the isomer(s) specified. There may be more than one possible isomer for each part. a. a cyclic compound that is an isomer of trans-2-butene b. an ester that is an isomer of propanoic acid c. a ketone that is an isomer of butanal d. a secondary amine that is an isomer of butylamine e. a tertiary amine that is an isomer of butylamine f. an ether that is an isomer of 2 -methyl-2-propanol g. a secondary alcohol that is an isomer of 2-methyl-2-propanol
Step-by-Step Solution
Verified Answer
a. Cyclobutane:
\(Cyclobutane:
H H H
\|/
H-C-C-H
/|\
H H H
\)
b. Methyl ethanoate:
\(
O
||\
H3C - O - C - H
\
H
\)
c. Butanone:
\(
H H O
|/\
H-C-C=C
\
H
\)
d. N-methylpropylamine:
\(
H H
| |
H H H C - N - C - H
| \
H \
H
\)
e. N,N-dimethylethylamine:
\(
H H
| |
H H H C - N - C - H
| \
H \
H
\)
f. Methyl propyl ether:
\(
H H H
| | \
H3C - O - C - H
\
H
\)
g. 2-butanol:
\(
H H O
|/\
H H C-C-C-H
\
H
\)
1Step 1: Draw trans-2-butene structure
Draw trans-2-butene, which has the molecular formula C4H8:
H H H
\ /
C = C - C - H
/
H
2Step 2: Draw the cyclic compound isomer
Draw the cyclic compound isomer, which is cyclobutane:
H H H
\|/
H-C-C-H
/|\
H H H
b. An ester that is an isomer of propanoic acid:
3Step 1: Draw propanoic acid structure
Draw propanoic acid, which has the molecular formula C3H6O2:
H H O
|/\
H-C-C=C
\
OH
4Step 2: Draw the ester isomer
Draw the ester isomer, which is methyl ethanoate:
O
||\
H3C - O - C - H
\
H
c. A ketone that is an isomer of butanal:
5Step 1: Draw butanal structure
Draw butanal, which has the molecular formula C4H8O:
O
||
C - H
\
C - H
\
C - H
\
C - H
\
H
6Step 2: Draw the ketone isomer
Draw the ketone isomer, which is butanone:
H H O
|/\
H-C-C=C
\
H
d. A secondary amine that is an isomer of butylamine:
7Step 1: Draw butylamine structure
Draw butylamine, which has the molecular formula C4H11N:
H
|
H H H N H
|/ /
H-C-C-C-C-H
\
H
8Step 2: Draw the secondary amine isomer
Draw the secondary amine isomer, which is N-methylpropylamine:
H H
| |
H H H C - N - C - H
| \
H \
H
e. A tertiary amine that is an isomer of butylamine:
9Step 1: Draw butylamine structure
Use the structure of butylamine shown in Step 1 of part d.
10Step 2: Draw the tertiary amine isomer
Draw the tertiary amine isomer, which is N,N-dimethylethylamine:
H H
| |
H H H C - N - C - H
| \
H \
H
f. An ether that is an isomer of 2-methyl-2-propanol:
11Step 1: Draw 2-methyl-2-propanol structure
Draw 2-methyl-2-propanol, which has the molecular formula C4H10O:
H H O
|/\
H H C-C-C-H
\
H
12Step 2: Draw the ether isomer
Draw the ether isomer, which is methyl propyl ether:
H H H
| | \
H3C - O - C - H
\
H
g. A secondary alcohol that is an isomer of 2-methyl-2-propanol:
13Step 1: Draw 2-methyl-2-propanol structure
Use the structure of 2-methyl-2-propanol already drawn in step 1 of part f.
14Step 2: Draw the secondary alcohol isomer
Draw the secondary alcohol isomer, which is 2-butanol:
H H O
|/\
H H C-C-C-H
\
H
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