Which reaction conditions will turn olive oil into a soap?

What are the products of the following reactions?

i.

j.

Propose a mechanism for the hydrolysis of N,N-dimethylacetamide

(a) under basic conditions.

Propose a mechanism for the hydrolysis of N,N-dimethylacetamide

(b) under acidic conditions.

Propose a mechanism for the basic hydrolysis of benzonitrile to the benzoate ion and ammonia.

D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted ­hydrolysis of an ester is the acyl C—O bond, rather than the alkyl C—O bond, by studying the hydrolysis of the following ester under basic conditions:

a. What products contained the ¹⁸O label?

b. What product would have contained the ¹⁸O label if the alkyl C—O bond had broken?

The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of the ester group. Propose a mechanism for the reaction.

Predict the products and propose mechanisms for the following reactions.

(b)

Suppose we have some optically pure (R)-2-butyl acetate that has been 'labeled' with the heavy ¹⁸O isotope at one oxygen atom as shown.

(a) Draw a mechanism for the hydrolysis of this compound under basic conditions. Predict which of the products will contain the ¹⁸O label. Also predict whether the butan-2-ol product will be pure (R), pure (S), or racemized.