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Chapter 21: Q37P-a (page 1130)

Show how you would accomplish the following syntheses using amides as intermediates.

You may use any necessary reagents.

(a)benzoicacid鈫�benzyldimethylamine

Short Answer

Expert verified

Syntheses of benzyldimethylamine from benzoic acid and amide as intermediate as given below,

Step by step solution

01

Step-by-Step SolutionStep 1: Reaction of benzoic acid with thionyl chloride (SOCI2)

The benzoic acid reacts with thionyl chloride(SOCl2) to give the benzoyl chloride as a first product in above reaction.

02

Formation of amide intermediate

When benzoyl chloride are react with dimethyl amine then there is a formation of amide.

03

Use of LiAIH4 reagent

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.

04

Synthesis of benzyldimethylamine from amide as intermediate.

When N-dimethyl benzamide react with strong reducing reagentLiAIH4andH2O then there is a formation of benzyldimethylamine.

Synthesis of benzyldimethylamine

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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.

Macrolide antibiotics, including erythromycin and azithromycin (), contain a large ring lactone. One of the largest ever reported is Gargantulide A, the structure of which was determined by the research group of Prof. William Gerwick of the Scripps Institution of Oceanography (Organic Letters, 2015, 17, 1377鈥�1380). Isolated from a Streptomyces bacterium, it kills pathogenic bacteria like MRSA and Clostridium difficile, but it proved too toxic to the test animals to continue further testing.

(a) Identify the lactone that makes this a macrolide structure.

(b) How many rings does this structure contain? How many atoms are in the largest ring?

(c) Many complex NMR experiments were used to determine the stereochemistry of most, but not all, of the chiral centers. How many chiral centers does the structure contain?

(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?

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

The IR spectra shown next may include a carboxylic acid, an ester, an amide, a nitrile, an acid chloride, or an acid anhydride.

Determine the functional group suggested by each spectrum, and list the specific frequencies you used to make your decision.
See all solutions

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