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Chapter 21: Q56P (page 1142)

One mole of acetyl chloride is added to a liter of triethylamine, resulting in a vigorous exothermic reaction. Once the reaction mixture has cooled, 1 mole of ethanol is added. Another vigorous exothermic reaction results. The mixture is analyzed and found to contain triethylamine, ethyl acetate, and triethylammonium chloride. Propose mechanisms for the two exothermic reactions.

Short Answer

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Formation of salt

Formation of ethoxy methyl carbonate

Step by step solution

01

The reaction of acetyl chloride with triethylamine

The acetyl chloride reacts with triethylamine to form a salt instead of a stable amide as it has no hydrogen to lose and triethylamine is a nucleophile.

Formation of salt

02

Formation of ethoxy methyl carbonate

The salt reacts with ethyl alcohol to form ethoxy methyl carbonate. The following reaction is represented as follows:

Formation of ethoxy methyl carbonate

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Most popular questions from this chapter

Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.(c)pyrrolidine鈫�N-acetylpyrrolidine

Show how you would use anhydrides to synthesize the following compounds. In each

case, explain why an anhydride might be preferable to an acid chloride.

(d) succinic acid monomethyl ester

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

(a)phenylaceticacidphenylacetonitrile

(b)phenylaceticacid鈫�3-phenylpropionitrile

(c)p-chloronitrobenzenep-chlorobenzonitrile

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

(a) ethyl propionate

(b)phenyl 3-methylhexanoate

(c)benzyl benzoate

(d)cyclopropyl cyclohexanecarboxylate

(e)tert-butyl acetate

(f) diallyl succinate

(a)Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.

(b) Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.

(c)Propose a secondmechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the otheroxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.

(d)Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.

(e)Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an SN2 reaction?
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