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Saturday, 31 October

JEE Main 2022 · ChemistryMultiple choiceOtherMediumApplication

JEE Main 26 July 2022, Shift 2, Chemistry Q76

Question 76 of 90 in this shift, Chemistry question 16 of 30, Section A.

[figure: EtO−C(=O)−H2C−\mathrm{EtO-C(=O)-H_2C-} attached to a five-membered ring having one double bond, with −CH2CH2CN\mathrm{-CH_2CH_2CN} attached to another ring carbon] →(i) DiBAL-H, (ii) H2O\xrightarrow{\text{(i) DiBAL-H, (ii) } \mathrm{H_2O}} ? [Et is −C2H5\mathrm{-C_2H_5}] Consider the above reaction and predict the major product.

The figure, in words

Reactant: five-membered carbocyclic ring with one double bond (drawn at the lower edge), bearing EtO−C(=O)−H2C−\mathrm{EtO-C(=O)-H_2C-} on the left and −CH2CH2CN\mathrm{-CH_2CH_2CN} on the right. Reagents (i) DiBAL-H (ii) H2O\mathrm{H_2O} over the arrow.
  1. (1)[figure: OHC−H2C−\mathrm{OHC-H_2C-} on the five-membered ring (one double bond), −CH2CH2CHO\mathrm{-CH_2CH_2CHO} on the ring]Official answer
  2. (2)[figure: EtO−C(=O)−H2C−\mathrm{EtO-C(=O)-H_2C-} on the five-membered ring (one double bond), −CH2CH2CHO\mathrm{-CH_2CH_2CHO} on the ring]
  3. (3)[figure: EtO−C(=O)−H2C−\mathrm{EtO-C(=O)-H_2C-} on the five-membered ring (one double bond), −CH2CH2COOH\mathrm{-CH_2CH_2COOH} on the ring]
  4. (4)[figure: OHC−H2C−\mathrm{OHC-H_2C-} on the five-membered ring (one double bond), −CH2CH2COOH\mathrm{-CH_2CH_2COOH} on the ring]

Official answer

Option 1

NTA final key.

Chapter
Aldehydes, Ketones and Carboxylic Acids
Topic
No close match in our taxonomy
Idea tested
No close match in our taxonomy

Question text from the official JEE Main paper published by NTA; answer from the final answer key. Chapter, topic and idea tags, difficulty and skill are Lumi’s. This question needs a figure we do not reproduce; it is described in words above. Lumi analyses 108 of the 174 JEE Main shifts held from 2017 to 2026.