Chapter 14, Problem 60IP

Interpretation Introduction

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

Concept Introduction:

Intramolecular ${\text{S}}_{\text{N}}\text{2}$ 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. $\text{NaOEt}$: 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. $\text{mCPBA}$: $\text{meta-Chloro-peroxybenzoic acid}$ 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 synthetic route for the given reaction to be identified.