(a) Only the trans isomer of 2-bromocyclohexanol can react with sodium hydroxide to form an oxacyclopropane-containing product. Explain the lack of reactivity of the cis-isomer.
(b) The synthesis of some oxacyclopropane-containing steroids has been achieved by use of a two-step procedure starting with steroidal bromoketones. Suggest suitable reagents for accomplishing a conversion such as the following one.

(c) Here in the first step, the attack of hydride ion takes place from the comparatively more stencally hindered side, that is the side of the bromine. This causes the formation of trans isomer.

This step has successful stereochemical requirement for the formation of oxacyclopropane?

Transcribed Image Text:

Br CH3 CH H CH H HIH HIH HO Br CH Br OH CH CH CH Ho