JEE Main Chemistry question

Which of the following reactions is *not* expected to give the major (Zaitsev) alkene in yields of more than 50%?

(A)A tertiary alcohol + conc. HSO, (acid-catalysed E1 dehydration, favours the more stable alkene)
(B)A tertiary bromide + bulky (CH)COK, (E2 with a bulky base favours the less hindered, Hofmann alkene)Correct
(C)A tertiary bromide + Zn/acetone (reductive dehalogenation, not an elimination to alkene at all)
(D)None of the above — all give the major alkene cleanly

Answer: (B)

Solution

A bulky base such as potassium *tert*-butoxide cannot easily approach the more substituted (and more hindered) -hydrogens needed to form the Zaitsev alkene; it instead removes the more

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Question ID VK-142380