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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

When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for the formation of this lactone.

Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.

(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?

(a)Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize

(i) benzyl acetate and

(ii) N,N-diethylacetamide.

(b)Propose a mechanism for each synthesis in part (a).

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

e. PhCH2OH
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