22. Carboxylic Acid Derivatives: NAS

What products would you expect to obtain from the following reactions?

b. methyl carbamate + methylamine

Show how the following compounds can be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

a.

Propose a mechanism for each of the following reactions:

b.

Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.

Predict the products of the following reactions.

(a) phenol + acetic anhydride

(b) phenol + acetic formic anhydride

(c) aniline + phthalic anhydride

Predict the products of the following reactions.

(j)

Predict the products of the following reactions:

(i)

There are many methods for activating a carboxylic acid in preparation for coupling with an amine. The following method converts the acid to an N-hydroxysuccinimide (NHS) ester.

(c) Propose a mechanism for the reaction of the NHS ester with an amine, R–NH₂.

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(c) benzyl benzoate

(d) cyclopropyl cyclohexanecarboxylate

Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a) propiophenone from propionic acid (using Friedel–Crafts acylation)

Predict the products of the following reactions:.

(h)

Predict the products of the following reactions.

(i)

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.

(b) Predict the products formed when phosgene reacts with 1 equivalent of methanol, followed by 1 equivalent of aniline.

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol → isopentyl acetate (banana oil)

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile