Question

Predict the product of the given reaction and find out the degree of unsaturation in the structure of the product.

Answer 1

t-butoxide (t-BuOK) can be used to form the “less substituted” alkenes in elimination reactions (the E2, specifically). Most of the time, elimination reactions favor the “more substituted” alkene – that is, the Zaitsev product. However, when t-butoxide is used, it will preferentially remove the proton from the smaller group.

(1S,2S,4R)-2-bromo-1,4-dimethyl cyclohexane on treatment with potassium tert butoixde in tert butanol undergoes dehydrobromination to form

(3R,6S)-3,6-dimethylcyclohex-1-ene.

Degree of unsaturation (DOU)=2
One is due to the alkene and another is due to cycle.
Answer-$2$