JEE Main · 2024 · Shift-IhardALCO-038

Identify the product A and product B in the following set of reactions: CH3-CH=CH2 H2O, H+ Major product A CH3-CH=CH2…

Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question

Question

Identify the product A and product B in the following set of reactions:

\ceCH3CH=CH2\ceH2O,H+\ce{CH3-CH=CH2} \xrightarrow{\ce{H2O, H+}} Major product A

\ceCH3CH=CH2(i) (\ceBH3)2; (ii) \ceH2O2,OH\ce{CH3-CH=CH2} \xrightarrow{\text{(i) }(\ce{BH3})_2\text{; (ii) }\ce{H2O2, OH-}} Major product B

Options
  1. a

    A = \ceCH3CH2CH2OH\ce{CH3CH2CH2OH}, B = \ceCH3CH(OH)CH3\ce{CH3CH(OH)CH3}

  2. b

    A = \ceCH3CH(OH)CH3\ce{CH3CH(OH)CH3}, B = \ceCH3CH(OH)CH3\ce{CH3CH(OH)CH3}

  3. c

    A = \ceCH3CH(OH)CH3\ce{CH3CH(OH)CH3}, B = \ceCH3CH2CH2OH\ce{CH3CH2CH2OH}

  4. d

    A = \ceCH3CH2CH2OH\ce{CH3CH2CH2OH}, B = \ceCH3CH2CH2OH\ce{CH3CH2CH2OH}

Correct Answerc

A = \ceCH3CH(OH)CH3\ce{CH3CH(OH)CH3}, B = \ceCH3CH2CH2OH\ce{CH3CH2CH2OH}

Detailed Solution

Step 1: Acid-catalysed hydration (Markovnikov) → A

In acid-catalysed hydration of propene:

  • \ceH+\ce{H+} adds to C1 (terminal, less substituted) forming the more stable secondary carbocation at C2.
  • \ceH2O\ce{H2O} attacks C2.
  • A = propan-2-ol (\ceCH3CH(OH)CH3\ce{CH3CH(OH)CH3}, isopropanol) — Markovnikov product ✓

Step 2: Hydroboration-oxidation (Anti-Markovnikov) → B

In hydroboration:

  • \ceBH3\ce{BH3} adds B to the terminal C1 (less substituted, less hindered).
  • \ceH2O2/OH\ce{H2O2/OH-} oxidizes: -B is replaced by -OH at C1.
  • B = propan-1-ol (\ceCH3CH2CH2OH\ce{CH3CH2CH2OH}, n-propanol) — Anti-Markovnikov product ✓

Key conceptual insight:

These two methods convert the same alkene to two different alcohol isomers:

  • H+/H2O → secondary alcohol (Markovnikov)
  • BH3/H2O2 → primary alcohol (anti-Markovnikov)

Key Points to Remember:

  • Markovnikov hydration: -OH to more substituted C.
  • Hydroboration-oxidation: -OH to less substituted C (anti-Markovnikov, syn addition).
  • Both reactions are additions across the double bond but follow opposite regioselectivity.

Practice this question with progress tracking

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

Identify the product A and product B in the following set of reactions: CH3-CH=CH2 H2O, H+ Major… (JEE Main 2024) | Canvas Classes