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Chapter 19: Q27P (page 1020)

Show how to synthesize the following amines from the indicated starting materials by acylation–reduction.

(a) N-butylpiperidine from piperidine

(b) N-benzylaniline from anilinea

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Introduction

Acylation is the process of adding acyl group to a compound. After getting intermediate compound by acylation, LiAlH4 act as a reducing agent, it is a strong reducing agent used to reduce aldehyde, ketones ,carboxylic acids, esters.

02

(a)

When piperidine and butyryl chloride react an intermediate is form, which on further reduction by LiAlH4 gives N-butylpiperidine.

03

(b)

When aniline and benzoyl chloride react an intermediate is form, which on further reduction by LiAlH4 gives N-benzylaniline.

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Most popular questions from this chapter

Question. Which of the amines listed next is resolved into enantiomers? In each case, explain why interconversion of the enantiomers does or does not take place.

  1. Cis-2-methylcyclohexanamine
  2. N-ethyl-N-methylcyclohexanamine
  3. N-methylaziridine
  4. Ethylmethylanilinium iodide
  5. Methylethylpropylisopropylammonium iodide

Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.

  1. N,N-dimethyl hexane-2-amine (b) N,N-diethyl hexane-2-amine

(c) cyclohexyl dimethyl amine (d) N-ethyl piperidine

Question. (a) Show how fragmentation occurs to give the base peak at m/z 58 in the mass spectrum of ethyl propyl amine (N-ethylpropan-1-amine), shown below.

(b) Show how a similar cleavage in the ethyl group gives an ion of m/z72.

(c) Explain why the peak at m/z 72 is much weaker than the one at m/z 58.

(a) Show how fragmentation occurs to give the base peak at m/z 58 in the mass spectrum of ethyl propyl amine (N-ethylpropan-1-amine), shown below.

(b) Show how a similar cleavage in the ethyl group gives an ion of m/z72.

(c) Explain why the peak at m/z 72 is much weaker than the one at m/z 58.

The proton and 13C NMR spectra of a compound of formula C4H11N are shown here. Determine the structure of this amine, and give peak assignments for all of the protons in the structure.
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