Q.

Identify the reagents used for the following conversion

Question Image

see full answer

Start JEE / NEET / Foundation preparation at rupees 99/day !!

21% of IItians & 23% of AIIMS delhi doctors are from Sri Chaitanya institute !!
An Intiative by Sri Chaitanya

a

=LiAlH4,B=NaOH(aq)C=NH2NH2/KOH,ethylglycol

b

A -DIBAL-H,B=NaOH(aq),C=ZnHg/Con.HCl,Alc.KOH

c

A=LiAlH4,B=NaOH(alc)C=Zn/HCl

d

A -DIBAL-H,B=NaOH(aq),C=NH2NH2/KOH,ethylglycol

answer is C.

(Unlock A.I Detailed Solution for FREE)

Ready to Test Your Skills?

Check your Performance Today with our Free Mock Test used by Toppers!

Take Free Test

Detailed Solution

Question Image

Step-by-Step Explanation:

Step A: Conversion of ester to aldehyde

The ester group (−COOCH₃) is converted to an aldehyde (−CHO).

DIBAL-H (Diisobutylaluminium hydride) is the correct reagent for this reaction, as it reduces esters to aldehydes at low temperatures (-78°C).

LiAlH₄ would reduce the ester completely to a primary alcohol, which is not the desired product.

Reagent A = DIBAL-H

Step B: Aldol condensation

This step involves the reaction of two aldehydes (−CHO) to form a β-hydroxy aldehyde (aldol product), which then undergoes dehydration to form an α,β-unsaturated aldehyde.

NaOH (aqueous) is the standard reagent for aldol condensation. It facilitates the enolate formation and subsequent reaction.

Reagent B = NaOH (aq)

Step C: Cyclization and reduction

The final step involves the conversion of the α,β-unsaturated aldehyde into a saturated cyclic product.

NH₂-NH₂/KOH, ethylene glycol is a Wolff–Kishner reduction, which removes the carbonyl group (aldehyde) and yields the saturated hydrocarbon.

Other options, like Zn/Hg, HCl (Clemmensen reduction), are not consistent with the reaction conditions shown here.

Reagent C = NH₂-NH₂/KOH, ethylene glycol

Correct Answer:

Option B

  • A = DIBAL-H
  • B = NaOH (aq)
  • C = NH₂-NH₂/KOH, ethylene glycol
Watch 3-min video & get full concept clarity

hear from our champions

score_test_img

Get Expert Academic Guidance – Connect with a Counselor Today!

whats app icon