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Chapter 21: Q36P-a (page 1129)

Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.(a)N-ethylbenzamide鈫�benzylethylamine

Short Answer

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Synthetic transformation for N-ethylbenzamide to benzylethylamine is show as,

Step by step solution

01

Step-by-Step SolutionStep 1: Use of  LiAIH4reagent

LiAIH4is a strong reducing agent for polar double bonds, as it easily thought of as a source of H鈭� . It will reduce aldehydes, ketones,esters, carboxylic acid chloride, carboxylic acids and even carboxylate salts to alcohols.


LiAIH4is also reduce the amide and nitriles to amine, In above reaction amide is reduce to amine.

02

Synthesis of benzylethylamine from N-ethylbenzamide

When N-ethylbenzamide react withLiAIH4andH2Othen there is a formation of benzylethylamine, in this reaction carbonyl group are direct reduce to alkane.

Formation of benzylethylamine

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Most popular questions from this chapter

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

(a)N,N-dimethylacetamide

(b)acetanilide(PhNHCOCH3)

(c)cyclohexanecarboxamide

(d)

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.

(c) phthalic acid monoamide

Show how each transformation may be accomplished by using a nitrile as an intermediate.

You may use any necessary reagents.

(a)hexan-1-ol鈫�heptan-1-amine

(b)cyclohexanecarboxamide鈫�cyclohexylethylketone

(c)octan-1-ol鈫�decan-2-one

(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?

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.
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