Q. 75 E - Organic Chemistry (Mcmurry)

Question

We’ll see in Chapter 11 that alkyl halides react with hydrosulfide ion () to give a product whose stereochemistry is inverted from that of the reactant. 

Step-by-Step Solution

Answer

Stereochemistry of obtained product is $\mathbf{R}$.

Step 1: reaction

In reaction, one bond gets broken and another bond is formed simultaneously. This is a bimolecularand a single-step reaction. The rate of this reaction depends on the concentration of the reactant as well as the product. In this reaction, stereochemistry of the product is inverted. 

Step 2: Reaction of (S)-2-Bromobutane with

This is a reaction.in this reaction,attacks from the backside of bromine and we get a product with inverted stereochemistry. The reaction proceeds as follows.

This reaction is completed in a single step.bond forms and bond break simultaneously. So, the stereochemistry of obtaining product 2-butanethiol is R.