JEE Main · 2023 · Shift-ImediumHC-041

Choose the correct set of reagents for the following conversion: {trans}({Ph-CH=CH-CH3}) {cis}({Ph-CH=CH-CH3})

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

Choose the correct set of reagents for the following conversion: trans(\cePhCH=CHCH3)cis(\cePhCH=CHCH3)\text{trans}(\ce{Ph-CH=CH-CH3}) \rightarrow \text{cis}(\ce{Ph-CH=CH-CH3})

Options
  1. a

    \ceBr2\ce{Br2}, alc \ceKOH\ce{KOH}, \ceNaNH2\ce{NaNH2}, \ceNa(Liq. NH3)\ce{Na(Liq.\space NH3)}

  2. b

    \ceBr2\ce{Br2}, alc \ceKOH\ce{KOH}, \ceNaNH2\ce{NaNH2}, \ceH2\ce{H2}, Lindlar Catalyst

  3. c

    \ceBr2\ce{Br2}, aq \ceKOH\ce{KOH}, \ceNaNH2\ce{NaNH2}, \ceH2\ce{H2}, Lindlar Catalyst

  4. d

    \ceBr2\ce{Br2}, aq \ceKOH\ce{KOH}, \ceNaNH2\ce{NaNH2}, \ceNa(Liq. NH3)\ce{Na(Liq.\space NH3)}

Correct Answerb

\ceBr2\ce{Br2}, alc \ceKOH\ce{KOH}, \ceNaNH2\ce{NaNH2}, \ceH2\ce{H2}, Lindlar Catalyst

Detailed Solution

image Step 1: Understand the conversion required

Convert trans-\cePhCH=CHCH3\ce{Ph-CH=CH-CH3} (trans-1-phenylpropene) → cis-\cePhCH=CHCH3\ce{Ph-CH=CH-CH3} (cis-1-phenylpropene)

Direct interconversion of cis/trans isomers requires breaking the π\pi bond — not possible by simple rotation. Need a multi-step synthesis.

Step 2: Plan the synthetic route

Strategy: Convert the alkene → alkyne → back to cis-alkene

Answer: Option (b)

Key Points to Remember:

  • Alc. KOH = β\beta-elimination; Aq. KOH = substitution
  • Lindlar's catalyst → cis-alkene from alkyne
  • \ceNa/LiqNH3\ce{Na/Liq NH3} (Birch) → trans-alkene from alkyne
  • Trans alkene → alkyne → cis alkene via Lindlar's route

Practice this question with progress tracking

Want timed practice with adaptive difficulty? Solve this question (and hundreds more from Hydrocarbons) inside The Crucible, our adaptive practice platform.

Choose the correct set of reagents for the following conversion: {trans}({Ph-CH=CH-CH3})… (JEE Main 2023) | Canvas Classes