
- A
- B
- C
- D
View written solutionFree
Correct answer: D
The reaction scheme image/details are not visible in the prompt, so I must infer the intended transformation from the reagent choices.
1. Analyze the three-step reagent patterns
Each option gives three reagents , , and .
Step : vs DIBAL-H
- is a strong reducing agent.
- It reduces esters, acids, acyl chlorides, etc. generally all the way to alcohols.
- DIBAL-H is a controlled reducing agent.
- It reduces esters/nitriles under controlled conditions to aldehydes.
So if the intermediate after step must be a carbonyl compound (especially aldehyde), DIBAL-H is the more suitable reagent.
Step : vs
- generally favors hydrolysis/substitution.
- generally favors elimination to form an alkene.
Thus if the conversion requires formation of a double bond before the final step, alcoholic NaOH is appropriate.
Step : , ethylene glycol vs
These correspond to the two classic methods for deoxygenation of carbonyl compounds:
- , ethylene glycol: Wolff–Kishner reduction
- : Clemmensen reduction
Both reduce aldehydes/ketones to methylene groups.
So step must involve reduction of a carbonyl group to hydrocarbon.
2. Most plausible reaction logic
Among the options, the chemically most coherent sequence for a typical JEE conversion is:
- DIBAL-H creates an aldehyde selectively.
- Alcoholic NaOH carries out elimination to generate unsaturation.
- Zn/HCl reduces the carbonyl to .
This matches Option D.
3. Why other options are less suitable
Option A
- would over-reduce many carbonyl derivatives to alcohols, not aldehydes.
- is less consistent if elimination is needed.
Option B
- DIBAL-H is fine for selective reduction, but is not suited if alkene formation/elimination is required.
Option C
- again is too strong and usually gives alcohols.
- Though alcoholic NaOH and are individually plausible, the first step is generally inconsistent.
Option D
- DIBAL-H gives a controlled carbonyl intermediate.
- Alcoholic NaOH promotes elimination.
- Clemmensen reduction removes the carbonyl oxygen.
Hence this is the best fit.
4. Final answer
Therefore, the correct option is:
with
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