Question

When (1R,2R)-2-bromocyclohexanol is treated with a strong base, an epoxide (cyclic ether) is formed. Suggest a mechanism for formation of the epoxide: Draw step 1 of the mechanism. Include lone pairs and formal charges in your answer. Do not explicitly draw out any hydrogen atoms in this step of the mechanism EXCEPT for the hydrogen on the oxygen atom of the organic starting material.

Answer 1

Here's what I get

Step-by-step explanation:

In Step 1, the hydroxide ion removes a proton from the OH group (acid-base equilibrium).

In Step 2, the alkoxide non undergoes an internal SN2 attack on the back side of the carbon bearing the bromine.

The bromide ion is ejected, and the final product is the epoxide.