Question

1. Draw compounds B and C from the following reaction scheme.

Br2. NaOH H2O CH3 excess NH3 SOCl2 CH3

2. Propose a structure for the product of this reaction.

Answer 1

Carboxylic acids react with SOCl2 to give acidchlorides. Thus, pivalic acid react with SOCl2 to give pivaloyl chloride CH3 O CH3 O SOCI pivalic acid pivaloyl chloride Acid chlorides react with excess NH3 to give amides. Thus, pivaloyl chloride react with excess ammonia to give pivalamide CH3 O CH3 O Excess NH3 pivaloyl chloride pivalamide Amide react with Br2 in the presence of NaOH gives amines with one less carbon of starting material Thus, pivalamide reacts with bromine molecule in the presence of NaOH to give 2-methylpropan-2-amine CH3 CH3 O Br2/NaOH H3C 2-methylpropan-2-amine pivalamide Overall reaction is as follows: pivalamide CH3 O CH3 O CH3 O SOCI Excess NH3 pivalic acid pivaloyl chloride Br2/NaOH CH3

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4-methyl-5-oxopentanenitrile undergoes catalytical reduction to give 2-methylpiperidine H2,Pt CH3 2-methylpiperidine Chemical Formula: C,H3N 4-methyl-5-oxopentanenitrile