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Chapter 19: Q15P (page 999)

Propose a mechanism to show the individual alkylations that form this quaternary ammonium salt.

Short Answer

Expert verified

Alkylation is the migration of an alkyl substituent from one molecule to another through an alkyl carbocation, a carbanion, a free radical, and a carbene, which are generated from electrophilic alkylating agents like alkyl halide in the presence of a strong mineral acid.

Step by step solution

01

Introduction

Alkylation is the migration of an alkyl substituent from one molecule to another through an alkyl carbocation, a carbanion, a free radical, and a carbene, which are generated from electrophilic alkylating agents like alkyl halide in the presence of a strong mineral acid.

02

Alkylation to tetraalkylammonium salt

Propylene amine donates a lone pair from N to methyl iodide to form a bond. A mild base NaHCO3 is added to deprotonate the intermediate alkylated amines and to neutralize the large quantities of HX formed.

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Most popular questions from this chapter

Predict the products from the reactions of the following amines with sodium nitrite in dilute.

  1. Cyclohexanamine
  2. N-ethylhexan-2-amine
  3. Piperidine
  4. Aniline

Question. (a) Propose a mechanism for the reaction of 2-bromopyridine with sodium amide to give 2-aminopyridine.

(b) When 3-bromopyridine is used in this reaction, stronger reaction conditions are required and a mixture of 3-aminopyridine and 4-aminopyridine results. Propose a mechanism to explain this curious result.

(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.

Show how you would convert aniline to the following compounds

(a)flurobenzene (b) chlorobenzene

(c) 1,3,5- trimethylbenzene(d) bromobenzene

(e) iodobenzene(f) benzonitrile

(g) phenol

(h)

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
See all solutions

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