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Consider the following reactions: (a) (CH3)3CCH(OH)CH3 —conc. H2SO4→ (b) (CH3)2CHCH(Br)CH3 —conc. KOH→ (c) (CH3)2CHCH(Br)CH3 —(CH3)3O−K+→ (d) (CH3)2C(OH)CH2CHO —Δ→ Which of these reactions(s) will not produce Saytzeff product ?

1. (1) (d) only
2. (2) (c) only
3. (3) (b) and (d)
4. (4) (a), (c) and (d)

Correct answer: (2) (c) only

Solution

With bulky (CH3)3CO-K+ (potassium tert-butoxide) on 2-bromo-3-methylbutane, the less-substituted Hofmann alkene dominates, so reaction (c) does NOT give the Saytzeff product; the others give the more-substituted/stable alkene.

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