Question

Using the pK_avalues listed in Table 15.1, predict the products of the following reaction:

Short answer

(a)

no reaction

(b)

Formation of acetic acid

(c)

No reaction

No reaction

Step-by-step solution

Nucleophilic addition-elimination reaction

All the carboxylic acid derivatives undergo nucleophilic addition-elimination by the following mechanism.The nucleophile adds to the carbonyl carbon, forming a tetrahedral intermediate. The weaker of the two bases is eliminated because either the group was attached to the acyl group in the reactant or the newly added group or the pi bond reforms.

The formation of the products for the following reactions:

(a)

No reaction

Methyl acetate cannot be converted into an acyl chloride because a chloride ion is a weaker base than an alkoxide ion which is represented as follows:

(b)

The following reaction represents Cl as a weaker base than OH nucleophile. So, Cl nucleophile can be eliminated and forms acetic acid which is represented as

Formation of acetic acid

(c)

An acetamide cannot be converted into an acyl chloride because a chloride ion is a weaker base than an amine nucleophile.

No reaction

(d)

An acetamide cannot be converted into an acid because a hydroxide ion is a weaker base than an amine nucleophile.

No reaction