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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

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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

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.

(a)Cis-2-methylcyclohexanamine

(b) N-ethyl-N-methylcyclohexanamine

(c) N-methylaziridine

(d) Ethylmethylanilinium iodide

(e) Methylethylpropylisopropylammonium iodide

When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofman product.

  1. Draw the structure of the major (Hofman) product.
  2. Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with m-CPBA and heated, the Zaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations.

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(a) Explain this order:

The following partial IR spectra correspond to a primary amine, a secondary amine, and an alcohol. Give the functional group for each spectrum.

Question. Propose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at 3-position.
See all solutions

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