JEE Main · 2019 · Shift-IeasyHC-058

The major product of the following addition reaction is:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

The major product of the following addition reaction is: image

Options
  1. a

    Option A

  2. b

    Option B

  3. c

    Option C

  4. d

    Option D

Correct Answerc

Option C

Detailed Solution

Step 1: Identify the starting material and reaction

The starting material is propene (\ceCH3CH=CH2\ce{CH3-CH=CH2}) or a similar alkene being treated with \ceCl2/H2O\ce{Cl2/H2O} (chlorine water).

Step 2: Reaction of alkene with \ceCl2/H2O\ce{Cl2/H2O}

\ceCl2\ce{Cl2} in the presence of water undergoes halohydrin formation:

  1. \ceCl+\ce{Cl^+} (or \ceCl2\ce{Cl2}) adds to the double bond forming a chloronium ion intermediate
  2. Water (the nucleophile) attacks the more electrophilic carbon (more substituted = Markovnikov)
  3. \ceCl\ce{Cl-} attacks from the opposite face of the more substituted carbon

Step 3: Product image Answer: Option (c)

Key Points to Remember:

  • \ceCl2/H2O\ce{Cl2/H2O} = chlorine water → gives chlorohydrin
  • \ceOH\ce{OH} goes to the more substituted carbon (Markovnikov position)
  • \ceCl\ce{Cl} goes to the less substituted carbon
  • Anti addition: \ceOH\ce{OH} and \ceCl\ce{Cl} on opposite faces

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