JEE Main · 2019 · Shift-ImediumHALO-114

The major product of the following reaction is:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

The major product of the following reaction is: image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerd

image

Detailed Solution

Step 1: Identify the starting material

From the image: Dibromide with phenyl group

Likely structure: \cePhCHBrCHBrCH2CH3\ce{Ph-CHBr-CHBr-CH2-CH3} (vicinal dibromide)

Step 2: Reaction with excess alcoholic KOH

Alcoholic KOH (excess) + heatDouble elimination

Vicinal dibromides undergo two E2 eliminations to form alkynes

Step 3: Mechanism

First elimination: \cePhCHBrCHBrR>[KOH]PhCH=CBrR+KBr+H2O\ce{Ph-CHBr-CHBr-R ->[KOH] Ph-CH=CBr-R + KBr + H2O}

Forms vinyl bromide intermediate

Second elimination: \cePhCH=CBrR>[KOH/Δ]PhCCR+KBr+H2O\ce{Ph-CH=CBr-R ->[KOH/Δ] Ph-C≡C-R + KBr + H2O}

Forms alkyne

Step 4: Final product

Product: Phenylacetylene derivative (alkyne)

Structure: \cePhCCCH2CH3\ce{Ph-C≡C-CH2-CH3}

Answer: (d) Alkyne structure

Key Concepts:

Vicinal dihalides → Alkynes:

General reaction: \ceRCHXCHXR+2KOH(alc)>[excess/Δ]RCCR+2KX+2H2O\ce{R-CHX-CHX-R' + 2 KOH(alc) ->[excess/Δ] R-C≡C-R' + 2 KX + 2 H2O}

Requirements:

  • Excess strong base
  • Heat
  • Two equivalents of base needed

Mechanism:

  • First E2: Forms vinyl halide
  • Second E2: Forms alkyne
  • Vinyl halides are less reactive but react under forcing conditions

Alternative with geminal dihalides: \ceRCX2CH2R+2KOH(alc)>RCCR\ce{R-CX2-CH2-R' + 2 KOH(alc) -> R-C≡C-R'}

Also forms alkynes via similar double elimination.

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