Consider the above chemical reaction. Product "A" is:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
Consider the above chemical reaction. Product "A" is:
- a
- b✓
- c
- d
Step 1: Identify the reaction conditions
Cyclohexyl chloride with methyl substituent + NaOH in water (aqueous)
Aqueous NaOH → substitution favored (not elimination)
Step 2: Determine the mechanism
mechanism:
- Backside attack by
- 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:
- Where Cl was originally
- Stereochemistry (inversion if chiral center)
Step 4: Determine stereochemistry
If the starting material has:
- Cl at C-1
- at C-2 (or other position)
After :
- OH at C-1 (inverted configuration)
- remains at same position
Option (b) shows cyclohexanol with OH and in specific positions, suggesting the correct stereochemical outcome.
Answer: (b)
Key Points:
- Aqueous NaOH → substitution (primary/secondary halides)
- Alcoholic NaOH → E2 elimination
- → Inversion of configuration (Walden inversion)
- Cyclohexane conformations: equatorial substituents more stable
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