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Chapter 20: Q18P c. (page 1065)

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

(a)

(b)

(c)

Short Answer

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(c)

Step by step solution

01

 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.

02

Reaction of N, N-dimethylformamide(DMF)

Synthesis of N,N-dimethylformamide(DMF)

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Most popular questions from this chapter

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (“Et” is the abbreviation for ethyl.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Question: Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(b). Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:

(a)Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetric carbon atom. (Using your models may be helpful.)

(b)Determine the relationship between the two stereoisomers you have drawn.

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32°C)

(c) ethyl phenylacetate
See all solutions

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