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Chapter 21: Problem 60

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

Short Answer

Expert verified
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: \( H H O |/\ H H C-C-C-H \ H \)

Step by step solution

01

Draw trans-2-butene structure

Draw trans-2-butene, which has the molecular formula C4H8: H H H \ / C = C - C - H / H
02

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:
03

Draw propanoic acid structure

Draw propanoic acid, which has the molecular formula C3H6O2: H H O |/\ H-C-C=C \ OH
04

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:
05

Draw butanal structure

Draw butanal, which has the molecular formula C4H8O: O || C - H \ C - H \ C - H \ C - H \ H
06

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:
07

Draw butylamine structure

Draw butylamine, which has the molecular formula C4H11N: H | H H H N H |/ / H-C-C-C-C-H \ H
08

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:
09

Draw butylamine structure

Use the structure of butylamine shown in Step 1 of part d.
10

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:
11

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
12

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:
13

Draw 2-methyl-2-propanol structure

Use the structure of 2-methyl-2-propanol already drawn in step 1 of part f.
14

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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Most popular questions from this chapter

All amino acids have at least two functional groups with acidic or basic properties. In alanine, the carboxylic acid group has \(K_{a}=4.5 \times 10^{-3}\) and the amino group has \(K_{b}=7.4 \times 10^{-5}.\) Three ions of alanine are possible when alanine is dissolved in water. Which of these ions would predominate in a solution with \(\left[\mathrm{H}^{+}\right]=1.0 \mathrm{M} ?\) In a solution with \(\left[\mathrm{OH}^{-}\right]=1.0 \mathrm{M} ?\)

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