91Ó°ÊÓ

When hydride ion removes a proton from the OH group, the alkoxide ion cannot react in an intramolecular reaction with the alkyl chloride to form an epoxide, because it cannot reach the back side of the carbon attached to the chlorine. Thus, the major product will result from an intermolecular reaction.

Hydride ion removes a proton from the OH group more rapidly than it attacks the alkyl chloride. Once the alkoxide ion is formed, it attacks back side of the alkyl chloride, forming an epoxide.

Hydride ion removes a proton from the OH group, and the alkoxide ion attacks the back side of the carbon attached to the bromine, forming a six-membered ring ether.

Hydride ion removes a proton from the OH group, and the alkoxide ion attacks the back side of the carbon attached to the chlorine, forming an epoxide.

After the halohydrin if formed, hydride ion removes a proton from the OH group and the alkoxide ion forms an epoxide