22. Carboxylic Acid Derivatives: NAS

Predict the products of the following reactions.

(b)

Predict the products and propose mechanisms for the following reactions.

(d)

Predict the products of the following reactions.

(a)

Draw the product of each of the following reactions:

b.

Predict the product of the following reaction sequences.

(a)

Predict the products of the following reactions.

(j)

Determine the major product for the following reaction.

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(a) Predict the products formed when phosgene reacts with excess propan-2-ol.

b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).

Show how you would convert the following starting materials to the indicated nitriles:

(a) phenylacetic acid → phenylacetonitrile

Predict the products of the following reactions:.

(h)

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(a) N,N-dimethylacetamide

(b) acetanilide (PhNHCOCH₃)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.

(g) 2-methylcyclopentyl acetate

(h) 1-bromo-1-methylcyclopentane

Write the mechanism for each of the following reactions:

a. the reaction of acetyl chloride with water to form acetic acid