Open Question
What carboxylic acids and amines result from hydrolysis of the following amides?
b. N,N-Dimethyl-p-nitrobenzamide
16. Carboxylic Acids and Their Derivatives
Amide Hydrolysis
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Name the carboxylic acid formed when the following amide undergoes an acidic hydrolysis reaction.
A
2-bromopentanoic acid
B
3-bromohexanoic acid
C
3-bromopentanoic acid
D
3-bromohexanoate
Verified step by step guidance1
Identify the structure of the amide: The given structure is an amide with a bromine atom on the third carbon of the chain. The amide linkage is between the carbonyl carbon and the nitrogen atom.
Understand the reaction: Acidic hydrolysis of an amide involves breaking the C-N bond of the amide linkage, resulting in the formation of a carboxylic acid and an amine.
Determine the carboxylic acid product: The carbonyl carbon of the amide becomes the carbonyl carbon of the carboxylic acid. The rest of the carbon chain, including the bromine substituent, remains unchanged.
Count the carbon atoms: The original amide has a total of six carbon atoms, including the carbonyl carbon. The bromine is on the third carbon, so the resulting carboxylic acid will have the same carbon skeleton.
Name the carboxylic acid: The carboxylic acid formed will have the bromine on the third carbon of a six-carbon chain, which is named 3-bromohexanoic acid.
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