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The product of dehydrohalogenation of 2-bromobutane with alc. KOH is mainly:

  1. (a) 1-butene
  2. (b) 2-butene
  3. (c) Butane
  4. (d) But-1-ene
Answer and solution

Answer (b) 2-butene

Solution

Chemistry ma’am · 4 steps

Two kinds of β-hydrogen here, and Saytzeff says the more substituted alkene wins.

  1. What alc. KOH does. Alcoholic KOH removes HBr: the Br leaves from C2 and a hydrogen leaves from a neighbouring (β) carbon, so a C=C forms between them.
  2. Find the β-carbons. In CH₃-CHBr-CH₂-CH₃ the carbon with Br is C2. Both C1 and C3 carry hydrogens, so two alkenes are possible.
    H removed fromProductAlkyl groups on the double bondShare
    C1But-1-ene, CH₂=CH-CH₂CH₃1 (monosubstituted)minor
    C3But-2-ene, CH₃-CH=CH-CH₃2 (disubstituted)major
  3. Saytzeff rule. When more than one alkene can form, the major product is the more substituted one. More alkyl groups on the double bond mean more hyperconjugation and a more stable alkene.
  4. So. The main product is 2-butene, option (b).

The idea to keep. In dehydrohalogenation, list every β-carbon that has a hydrogen. The alkene with more alkyl groups on the double bond is the major product (Saytzeff).

Answer from the NTA final answer key. Solution by PrepWiser.

Study Halogen Derivatives — Haloalkanes & Haloarenes

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