JEE Main 2017 · 2 Apr · Shift 1 · Chemistry Q59

ChemistrySingle correct+4 / -1Question 59 of 90

The correct sequence of reagents for the following conversion will be :

\ce{CH3MgBr}

\ce{[Ag(NH3)2]+OH-}

\ce{H+/CH3OH}

\ce{[Ag(NH3)2]+OH-}

\ce{CH3MgBr}

\ce{H+/CH3OH}

\ce{[Ag(NH3)2]+OH-}

\ce{H+/CH3OH}

\ce{CH3MgBr}

\ce{CH3MgBr}

\ce{H+/CH3OH}

\ce{[Ag(NH3)2]+OH-}

Answer and worked solution

Official answer: C

Tollens' reagent oxidises CHO to COOH and leaves the ketone.
$\ce{H+/CH3OH}$ esterifies it.
Excess $\ce{CH3MgBr}$ turns the ketone into a tertiary alcohol and the ester into $\ce{C(OH)(CH3)2}$ .

That is the sequence in (3). Adding the Grignard first would also attack the aldehyde.

JEE Main 2017 · 2 Apr · Shift 1, Chemistry question 59