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Carboxylic Acids and Derivatives
Nomenclature
1. Provide the IUPAC or common names for each compound.
2,2-dimethylpropanoyl chloride
cyclohexanecarboxylic anhydride
ethyl 3-methylhexanoate
cis-2-bromocyclohexanecarboxylic acid
-caprolactone
-valerolactam
1,3-benzenedicarboxylic acid
N,N-dimethylbenzamide
glutaric acid
2. Give the structure corresponding to each name.
(a) propanoic anhydride
(b) -chlorobutyryl chloride (c) cyclohexyl propanate
(e) isopropyl formate
(f) 4-methylheptanenitrile
(g) N,N-dibenzylformamide
(h) diethyl oxalate
(i) -valerolactone
(h) phthalic acid
Properties and Reactivity
3. Rank the compounds in order of increasing reactivity in nucleophilic acyl substitution.
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4. Explain why ester A is more reactive than ester B in nucleophilic acyl substitution.
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5. Explain why acetamide is a weaker base than ethylamine.
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6. Draw the organic products formed in each reaction.
Mechanisms
7. Draw a stepwise mechanism for each of the following reactions.
Synthesis
8. What carboxylic acid and alcohol are needed to prepare each ester by Fischer esterification?
9. Devise a synthesis of each compound using 1-bromobutane as the only organic starting
material. You may use any other inorganic reagents.
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10. Devise a synthesis of each compound from bromocyclohexane and any other organic or
inorganic reagents.
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