22. Carboxylic Acid Derivatives: NAS

Which compound forms an anhydride more rapidly?

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

a. sodium acetate

b. water

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.

(d) anisole and aluminum chloride

(e) excess phenylmagnesium bromide, then dilute acid

(f) LiAlH(O-t-Bu)₃

Predict the products of the following reactions.

(i)

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

i. isopropyl alcohol

a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):

Give the products expected from the following reactions.

(a) acetyl chloride + ethylamine

(b)

(c)

a. Identify the two products obtained from the following reaction:

Determine the major product for the following reaction.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

c.

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

(a) ethyl propionate

(b) phenyl 3-methylhexanoate

1. Propose a mechanism for the acid-catalyzed reaction of salicylic acid with acetic anhydride.

2. Explain why a single drop of sulfuric acid dramatically increases the reaction rate.

Grignard reagents add to carbonate esters as they add to other esters.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. Also show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin® insecticide.

Show how you would accomplish the following syntheses in good yields.

(g)