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Chapter 20: Q18P a. (page 1065)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Amines and carboxylic acids

Amines are compounds containing the -NH2group and carboxylic compounds with the –COOH group.Different reagents are used to prepare acid derivatives, such as amide HNCH2CH32is used. The formation of amide by using industrial methods needs high temperature.

02

Synthesis of N, N-diethyl-meta-toluamide

(a) When 3-methyl benzoic acid is treated with HNCH2CH32, a carboxylate anion is formed and, on heating, COO-is converted toCONEt2 . The product created is N, N-diethyl-meta-toluamide.


Synthesis of N, N-diethyl-meta-toluamide

03

Synthesis of acetanilide 

(b) When aniline is treated with acetic acid , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

04

Reaction of acetanilide 

Synthesis of acetanilide

05

Synthesis of N, N-dimethylformamide(DMF)

(c) When aniline is treated with acetic acid (CH3COOH) , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

06

Reaction of N, N-dimethylformamide(DMF) 

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Most popular questions from this chapter

Question: Draw all four resonance forms of the fragment at m/z 73 in the mass spectrum of pentanoic acid.

Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

a)

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(a) Predict the products formed when phosgene reacts with excess propan-1-ol.

(b) Predict the products formed when phosgene reacts with 1 equivalent of ethanol, followed by 1 equivalent of aniline.

(c) Iso-butyloxycarbonyl chloride is an important reagent for the synthesis of peptides and proteins. Show how you would use phosgene to synthesize iso-butyloxycarbonyl chloride.

Isobutyloxycarbonyl chloride

Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

c)

Use chemical equations to show how the following accidents cause injury to the clothing involved (not to mention the skin under the clothing!)

  1. An industrial chemist spills aqueous H2SO4on her nylon stockings but fails to wash it off immediately.
  2. An organic laboratory student spills aqueous NaOHon his polyester slacks.
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