JEE Main · 2024 · Shift-IImediumHALO-049

Consider the above chemical reaction. Product "A" is:

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

Question

image Consider the above chemical reaction. Product "A" is:

Options
  1. a

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  2. b

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  3. c

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  4. d

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Correct Answerb

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Detailed Solution

Step 1: Identify the reaction conditions

Cyclohexyl chloride with methyl substituent + NaOH in water (aqueous)

Aqueous NaOH → SN2S_N2 substitution favored (not elimination)

Step 2: Determine the mechanism

SN2S_N2 mechanism:

  • Backside attack by \ceOH\ce{OH-}
  • Inversion of configuration
  • Cl replaced by OH

Step 3: Identify the product

Starting material: Chlorocyclohexane with methyl group

Product: Cyclohexanol with methyl group (OH replaces Cl)

The position of OH depends on:

  1. Where Cl was originally
  2. Stereochemistry (inversion if chiral center)

Step 4: Determine stereochemistry

If the starting material has:

  • Cl at C-1
  • \ceCH3\ce{CH3} at C-2 (or other position)

After SN2S_N2:

  • OH at C-1 (inverted configuration)
  • \ceCH3\ce{CH3} remains at same position

Option (b) shows cyclohexanol with OH and \ceCH3\ce{CH3} in specific positions, suggesting the correct stereochemical outcome.

Answer: (b)

Key Points:

  • Aqueous NaOHSN2S_N2 substitution (primary/secondary halides)
  • Alcoholic NaOH → E2 elimination
  • SN2S_N2Inversion of configuration (Walden inversion)
  • Cyclohexane conformations: equatorial substituents more stable

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