Q23E - Organic Chemistry (Mcmurry)

Question

Predict the product (s) and provide the mechanism for each reaction below.

Step-by-Step Solution

Answer

The product prediction and its mechanism for each of the reaction  with sodium hydroxide and upon Hydrolysis can be explained as follows.

a) Ammonia and hexanoic acid.

b) Ammonia and cyclobutanecarboxylate anion.

c) Ammonia and m-methylbenzamide.

d) Ammonia and cyclobutanecarboxylate ion.

 

Step 1: Production prediction and mechanism for (a)

The hydroxide ion’s nucleophilic attack of nitrile carbon in hexanenitrile will yield a product of imine anion. The next step gets protonated for the production of hydroxylamine. The hydroxide ion’s nucleophilic attack of carbonyl carbon and consecutive loss of amide ion will give hexanoic acid. The deprotonation happens and results in the carboxylate formation with ammonia liberation. The products are ammonia and hexanoic acid.

The  mechanism of formation can be denoted as,

Step 2: Production prediction and mechanism for (b)

The hydroxide ion’s nucleophilic attack of nitrile carbon in 2-methylbutanenitrile will yield a product of imine anion. The next step gets protonated for the production of hydroxylamine. The hydroxide ion’s nucleophilic attack of carbonyl carbon and consecutive loss of amide ion will give butanoic acid. The deprotonation happens results in the carboxylate formation with ammonia liberation. The product are ammonia and cyclobutanecarboxylate anion.

The  mechanism of formation can be denoted as

Step 3: Production prediction and mechanism for (c)

The hydroxide ion’s nucleophilic attack of nitrile carbon in m-methylbenzonitrile will yield a product of imine anion. The next step gets protonated for the production of 3-methylbenzamide. The hydroxide ion’s nucleophilic attack of carbonyl carbon and consecutive loss of amide ion will gives m-methylbenzoic acid. The deprotonation happens results in the carboxylate ion  formation with ammonia liberation. The products are ammonia and 1-methylbenzamide.

The formation mechanism can be denoted as,

Step 4: Production prediction and mechanism for (d)

The hydroxide ion’s nucleophilic attack of nitrile carbon in cyclobutanenitrile will yield a product of imine anion. The next step gets protonated for the production of hydroxylamine. The hydroxide ion’s nucleophilic attack of carbonyl carbon and consecutive loss of amide ion will give cyclobutane carboxyl acid. The deprotonation  results in the carboxylate formation with ammonia liberation. The product are ammonia and cyclobutanecarboxylate ion.

The formation mechanism can be denoted as,