JEE Main 2022 · 26 Jul · Shift 2 · Chemistry Q76

ChemistrySingle correct+4 / -1Question 76 of 90

$[\mathrm{Et\ is\ -C_2H_5}]$

Consider the above reaction and predict the major product.

\mathrm{OHC-H_2C}

-(cyclopentene)-

\mathrm{CH_2CH_2CHO}

\mathrm{EtO-CO-H_2C}

-(cyclopentene)-

\mathrm{CH_2CH_2CHO}

\mathrm{EtO-CO-H_2C}

-(cyclopentene)-

\mathrm{CH_2CH_2COOH}

\mathrm{OHC-H_2C}

-(cyclopentene)-

\mathrm{CH_2CH_2COOH}

Answer and worked solution

Official answer: A

DIBAL-H then water reduces an ester to an aldehyde and a nitrile (via the imine) to an aldehyde, so both ends become CHO.

(A)

JEE Main 2022 · 26 Jul · Shift 2, Chemistry question 76