Question 23.8: Write the products of the following reactions:...
Write the products of the following reactions:
\quad\quad \ CH_{3} \quad \ \ O\quad\quad\quad \quad \ \ \ CH_{3}\\ \quad\quad \ \ | \quad\quad \ \ \ \parallel \quad\quad\quad\quad \ \ \ | \\ \pmb{(a)} \quad CH_{3}CHCH_{2}COH + HOCHCH_{3} \longrightarrow \ ?\quad\quad Br \quad\quad\quad\quad \ \ O\\ \quad\quad \ | \quad\quad\quad\quad\quad \parallel \\ \pmb{(b)} \quad CH_{3}CH_{2}CHCH_{2}CNH_{2} + H_{2}O \longrightarrow \ ?
Step-by-Step
The reaction of a carboxylic acid with an alcohol yields an ester plus water, and the reaction of an amide with water yields a carboxylic acid and an amine (or ammonia). Write the reagents to show how H_{2}O is removed, and then connect the remaining frag-ments to complete the substitution reaction.
(a) \ CH_{3} \quad \ \ \ O \quad\quad\quad\quad\quad\quad\quad\quad \ \ \ CH_{3} \quad\quad\quad\quad \ \ CH_{3} \quad \ O \quad\quad\quad\quad CH_{3} \\ \quad\quad \ | \quad\quad\quad\parallel \quad\quad\quad\quad\quad\quad\quad\quad\quad| \quad\quad\quad\quad\quad\quad| \quad\quad \ \ \ \parallel \quad\quad\quad\quad| \\ CH_{3}CHCH_{2}C-OH + H-OCHCH_{3} \longrightarrow CH_{3}CHCH_{2}C-OCHCH_{3} + H_{2}O
(b) \quad\quad \ \ Br\quad\quad \ O\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad Br\quad\quad \ O\\\quad\quad\quad\quad \ \ \ | \quad\quad \ \ \ \parallel \quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad| \quad\quad \ \ \ \parallel \\ CH_{3}CH_{2}CHCH_{2}C-NH_{2} + H-OH \longrightarrow CH_{3}CH_{2}CHCH_{2}COH + NH_{3}
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