mMCQ.

Navigation Menu

Step into mMCQ.

Launch mMCQ. diagnostic

Explore mMCQ.

MDCAT prepFree DiagnosticPricing & SubscribeSign in

Resources

Terms & Conditions

mMCQ.

© 2021 - 2025 mMCQ.All rights reserved.

WhatsApp
A Levels Chemistry (9701)•9701/11/M/J/24
Question 32 from 9701/11/M/J/24

Explanation

Dehydration of chiral secondary alcohol to single alkene

Steps:

  • X is a pure optical isomer, so it has a chiral center and is likely a secondary alcohol.
  • Heating with excess H2SO4 triggers acid-catalyzed dehydration via E1, forming a planar carbocation and then an alkene.
  • For only one organic product, the reaction must yield a single alkene with no constitutional or geometric isomers possible.
  • Option D's structure allows carbocation formation leading exclusively to a terminal alkene like styrene, which is achiral and unique.

Why D is correct:

  • D is 1-phenylethanol; dehydration forms the benzylic carbocation PhCH(+)-CH3, which loses the methyl proton to give only PhCH=CH2 (Zaitsev's rule favors this conjugated alkene).

Why the others are wrong:

  • A: Aliphatic secondary alcohol like 2-butanol yields mixture of 1-butene, cis-/trans-2-butene.
  • B: Unsymmetric alcohol like 3-pentanol gives cis-/trans-2-pentene isomers.
  • C: Primary alcohol like 2-methyl-1-propanol dehydrates slowly to isobutene but may form ethers or multiple products under excess acid.

Final answer: D

Topic: Hydroxy compounds

Practice more A Levels Chemistry (9701) questions on mMCQ.me