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ChemistrySingle correct+4 / -1Question 67 of 75

JEE Main 2026 · 2 Apr · Shift 2, Chemistry question 67

A molecule (X) with following structure under mild acidic condition is hydrolysed to produce (Y) and (Z). Identify the correct statements about (Y) and (Z).

A. Both (Y) and (Z) have same molar mass.

B. (Y) and (Z) can be distinguished from each other by NaHCOX3\ce{NaHCO3}.

C. (Y) and (Z) react with HCN with same rates.

D. (Y) and (Z) undergo addition reaction with 2,4-DNP.

Choose the correct answer from the options given below :

(X): a divinyl ether, prop-1-enyl isopropenyl ether CH₃-CH=CH-O-C(CH₃)=CH₂, drawn as a skeletal formula.
Choose one option
Answer and worked solution

Official answer: D

Hydrolysis of the enol ether. Acid hydrolysis of CHX3CH=CH−O−C(CHX3)=CHX2\ce{CH3CH=CH-O-C(CH3)=CH2} releases the two enols, which tautomerise:

  • Y = propanal, CHX3CHX2CHO\ce{CH3CH2CHO};
  • Z = acetone, CHX3COCHX3\ce{CH3COCH3}.

Statements.

  • A ✓: both are CX3HX6O\ce{C3H6O}, 58 g mol⁻¹.
  • B ✗: neither is acidic enough to react with NaHCOX3\ce{NaHCO3}.
  • C ✗: aldehydes add HCN faster than ketones.
  • D ✓: both carbonyls form 2,4-DNP derivatives.

A and D.

(D)

Topics:Nucleophilic additionEthers
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