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JEE Main 202623 JanuaryMorning Shift
Exam
JEE Main
Year
2026
Date
23 January
Shift
Morning Shift
Subject
Chemistry
Chapter
Aldehydes and Ketones

JEE Main 2026 · 23 January · Morning Shift · Chemistry · Aldehydes and Ketones

' x ' is the product which is obtained from propanenitrile and...

' xx ' is the product which is obtained from propanenitrile and stannous chloride in the presence of hydrochloric acid followed by hydrolysis. ' yy ' is the product which is obtained from the but-2-ene by the ozonolysis followed by hydrolysis. From the following, which product is not obtained when one mole of ' xx ' and one mole of ' yy ' react with each other in the presence of alkali followed by heating?

Options

  1. A2-Methylpent-2-enal
  2. BPent-2-enal
  3. C2-Methylbut-2-enal
  4. D3-Methylbut-2-enal

Correct answer

D. 3-Methylbut-2-enal

Step-by-step solution

Product xx is obtained by the Stephen reduction of propanenitrile (CH3CH2CNCH_3CH_2CN).
CH3CH2CN→SnCl2/HClCH3CH2CH=NH→H2OCH3CH2CHOCH_3CH_2CN \xrightarrow{SnCl_2/HCl} CH_3CH_2CH=NH \xrightarrow{H_2O} CH_3CH_2CHO (Propanal).
Product yy is obtained by the reductive ozonolysis of but-2-ene (CH3CH=CHCH3CH_3CH=CHCH_3).
CH3CH=CHCH3→O3,H2O/Zn2CH3CHOCH_3CH=CHCH_3 \xrightarrow{O_3, H_2O/Zn} 2CH_3CHO (Ethanal).
When propanal (xx) and ethanal (yy) react in the presence of alkali followed by heating, they undergo cross-aldol condensation.
Possible products are:
1. Self-aldol of propanal: CH3CH2CHO+CH3CH2CHO→CH3CH2CH=C(CH3)CHOCH_3CH_2CHO + CH_3CH_2CHO \rightarrow CH_3CH_2CH=C(CH_3)CHO (2-Methylpent-2-enal).
2. Self-aldol of ethanal: CH3CHO+CH3CHO→CH3CH=CHCHOCH_3CHO + CH_3CHO \rightarrow CH_3CH=CHCHO (But-2-enal).
3. Cross-aldol (Ethanal as nucleophile): CH3CH2CHO+CH3CHO→CH3CH2CH=CHCHOCH_3CH_2CHO + CH_3CHO \rightarrow CH_3CH_2CH=CHCHO (Pent-2-enal).
4. Cross-aldol (Propanal as nucleophile): CH3CHO+CH3CH2CHO→CH3CH=C(CH3)CHOCH_3CHO + CH_3CH_2CHO \rightarrow CH_3CH=C(CH_3)CHO (2-Methylbut-2-enal).
Comparing with the options, 3-Methylbut-2-enal is not formed in any of these reactions.
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