ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
6th Edition
ISBN: 9781319306977
Author: LOUDON
Publisher: INTER MAC
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Chapter 25, Problem 25.31AP
Interpretation Introduction

Interpretation:

The mechanism for the formation of a racemic mixture of tert-butyl phosphate by heating the tetrabutylammonium salt of isotopically chiral phenyl phosphate in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol is to be drawn.

Concept introduction:

The tetrabutylammonium salt of isotopically chiral phenyl phosphate on heating in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol first forms planar metaphosphate ion which is gets trapped by the solvent acetonitrile from either side which racemizes the phosphate by nucleophilic attack of tert-butyl alcohol.

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Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.
(c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistry
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