Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
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Chapter 14, Problem 59IP
Interpretation Introduction

Interpretation: The efficient synthesis for the given reaction to be proposed.

Concept Introduction:

Intramolecular SN2 reaction: The groups like esters, sulfides, carboxylates, ethers, amines or alkoxide also assist substitution reactions through neighboring group participation. All must possess an electron-rich heteroatom with a lone pair of electron that can be used to form the cyclic intermediates or cyclic products.

Useful reagents:

  1. 1. NaOEt : An alkoxide ion is both a strong Nucleophile and a strong base. It can be used to open an epoxide under basic conditions(the alkoxide ion attacks the less substituted position)
  2. 2. mCPBA : meta-Chloro-peroxybenzoic acid is an oxidizing agent that will convert an alkene into an epoxide.
  3. 3. Grignard reagent: A strong base and a strong Nucleophile. Will react with an epoxide in a ring-opening reaction, to attack the less substituted side.

To Identify: The mechanism for the reaction to be identified.

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