Question

Question: When each halohydrin is treated with NaH a product of molecular formula${\mathbf{C}}_{\mathbf{4}}{\mathbf{H}}_{\mathbf{8}}\mathbf{O}$is formed. Draw the structure of the product and indicate its stereochemistry.

a.

b.

c.

Short answer

Answer

a.

b.

c.

Step-by-step solution

Step-by-Step SolutionStep 1: Halohydrins

The compounds with both -OH group and -X are referred to as halohydrins.

Reactions of halohydrins

The reaction of halohydrins with the strong base like NaH is an example of intramolecular Williamson ether synthesis.

This takes the path of ${\mathrm{S}}_{\mathrm{N}}2$reaction with inversion in stereochemistry at the carbon-containing halogen atom of the halohydrin

Explanation

The formation of the product${\mathrm{C}}_4{\mathrm{H}}_8\mathrm{O}$with each reaction and its structure is shown below:

a.

Formation of epoxide from a

b.

Formation of epoxide from b

c.

Formation of epoxide from c