Match List - I with List - II. List - I (Chemical Reaction) List - II (Reagent used) a ${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{2}{\mathrm{CH}}_{3}\rightarrow {\mathrm{CH}}_{3}{\mathrm{CH}}_{2}\mathrm{OH}$ i ${\mathrm{CH}}_{3}\mathrm{MgBr}/{H}_{3}{O}^{+}$ (one equivalent) b ${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{3}\rightarrow {\mathrm{CH}}_{3}\mathrm{CHO}$ ii ${H}_{2}{\mathrm{SO}}_{4}/{H}_{2}O$ c ${\mathrm{CH}}_{3}C\equiv N\rightarrow {\mathrm{CH}}_{3}\mathrm{CHO}$ iii $\mathrm{DIBAL}-H/{H}_{2}O$ d iv ${\mathrm{SnCl}}_{2},\mathrm{HCl}/{H}_{2}O$ Choose the most appropriate match.

JEE Main 2021 — Chemistry Organic Chemistry

2021mcqhard

Match List - I with List - II.

	List - I (Chemical Reaction)		List - II (Reagent used)
a	${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{2}{\mathrm{CH}}_{3}\rightarrow {\mathrm{CH}}_{3}{\mathrm{CH}}_{2}\mathrm{OH}$	i	${\mathrm{CH}}_{3}\mathrm{MgBr}/{H}_{3}{O}^{+}$ (one equivalent)
b	${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{3}\rightarrow {\mathrm{CH}}_{3}\mathrm{CHO}$	ii	${H}_{2}{\mathrm{SO}}_{4}/{H}_{2}O$
c	${\mathrm{CH}}_{3}C\equiv N\rightarrow {\mathrm{CH}}_{3}\mathrm{CHO}$	iii	$\mathrm{DIBAL}-H/{H}_{2}O$
d		iv	${\mathrm{SnCl}}_{2},\mathrm{HCl}/{H}_{2}O$

Choose the most appropriate match.

Official previous-year question

Held on 26 Aug 2021 · Verified 6 Jul 2026.

Options

A
$(a)-(\mathrm{ii}),(b)-(\mathrm{iii}),(c)-(\mathrm{iv}),(d)-(i)$
B
$(a)-(\mathrm{ii}),(b)-(\mathrm{iv}),(c)-(\mathrm{iii}),(d)-(i)$
C
$(a)-(\mathrm{iii}),(b)-(\mathrm{ii}),(c)-(i),(d)-(\mathrm{iv})$
D
$(a)-(\mathrm{iv}),(b)-(\mathrm{ii}),(c)-(\mathrm{iii}),(d)-(i)$

Did you get this right?

Solution

(a) ${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{2}{\mathrm{CH}}_{3}\overset{{H}_{2}{\mathrm{SO}}_{4}/{H}_{2}O}{\longrightarrow }{\mathrm{CH}}_{3}{\mathrm{CH}}_{2}\mathrm{OH}$ (Hydrolysis of ester)

(b) ${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{3}\overset{\mathrm{DIBAL}-H}{\longrightarrow }{\mathrm{CH}}_{3}\mathrm{CHO}$ (Reduction of ester)

(c) ${\mathrm{CH}}_{3}\equiv N\overset{{\mathrm{SnCl}}_{2},\mathrm{HCl}/{H}_{2}O}{\longrightarrow }{\mathrm{CH}}_{3}\mathrm{CHO}$ (Reduction followed by hydrolysis)

(d) JEE Main 2021 Chemistry, Carboxylic Acid Derivatives — solution figure (Nucleophillic addition reaction)

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Options

$(a)-(\mathrm{ii}),(b)-(\mathrm{iii}),(c)-(\mathrm{iv}),(d)-(i)$

$(a)-(\mathrm{ii}),(b)-(\mathrm{iv}),(c)-(\mathrm{iii}),(d)-(i)$

$(a)-(\mathrm{iii}),(b)-(\mathrm{ii}),(c)-(i),(d)-(\mathrm{iv})$

$(a)-(\mathrm{iv}),(b)-(\mathrm{ii}),(c)-(\mathrm{iii}),(d)-(i)$

Solution

(a) ${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{2}{\mathrm{CH}}_{3}\overset{{H}_{2}{\mathrm{SO}}_{4}/{H}_{2}O}{\longrightarrow }{\mathrm{CH}}_{3}{\mathrm{CH}}_{2}\mathrm{OH}$ (Hydrolysis of ester)

(b) ${\mathrm{CH}}_{3}{\mathrm{COOCH}}_{3}\overset{\mathrm{DIBAL}-H}{\longrightarrow }{\mathrm{CH}}_{3}\mathrm{CHO}$ (Reduction of ester)

(c) ${\mathrm{CH}}_{3}\equiv N\overset{{\mathrm{SnCl}}_{2},\mathrm{HCl}/{H}_{2}O}{\longrightarrow }{\mathrm{CH}}_{3}\mathrm{CHO}$ (Reduction followed by hydrolysis)

(d) JEE Main 2021 Chemistry, Carboxylic Acid Derivatives — solution figure (Nucleophillic addition reaction)

JEE Main 2021 — Chemistry Organic Chemistry

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JEE Main 2021 — Chemistry Organic Chemistry

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JEE Main Organic Chemistry in other years

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