Identify the products of the following named reactions: (i) propan-2-one (CH₃COCH₃) on Clemmensen reduction; (

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Q. Identify the products of the following named reactions:

(i) propan-2-one (CH₃COCH₃) on Clemmensen reduction;

(ii) benzonitrile (C₆H₅CN) on Stephen reaction.

Manipur CohsemCOHSEM Manipur Higher Secondary Board 2026Subjective· 2mImportance★★★★★

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Concept understanding — Clemmensen Reduction

Clemmensen Reduction: From Intuition to Precision

Imagine you have a ketone or an aldehyde — a molecule with a C=O group. You want to rip that oxygen out entirely and replace it with two hydrogens, turning the carbonyl carbon into a plain CH₂ group. That is exactly what the Clemmensen reduction does.

Why would you want that? Because sometimes you need a hydrocarbon chain where a carbonyl used to be. For example, if you have a ketone attached to a benzene ring, the Clemmensen reduction gives you an alkylbenzene — a common starting material in organic synthesis.

The reaction uses zinc amalgam (Zn-Hg) and concentrated hydrochloric acid (HCl). The zinc amalgam is simply zinc metal that has been treated with mercury to form an alloy — this makes the zinc surface more reactive and prevents side reactions.

\ce{R-C(=O)-R' + 4[H] ->[Zn-Hg, conc. HCl] R-CH2-R' + H2O}

The "4[H]" is a shorthand for the reducing equivalent supplied by the zinc in acid. The carbonyl oxygen leaves as water, and two hydrogens attach to the carbon.

The Mechanism (What Actually Happens)

The mechanism is not fully settled, but the most widely accepted path involves a carbocation intermediate. Here is the key insight: the reaction works because concentrated HCl protonates the carbonyl oxygen, making the carbon highly electrophilic. Zinc then donates electrons, and the oxygen leaves as water, leaving behind a positively charged carbon (a carbocation). That carbocation then picks up two hydride-like hydrogens from the zinc surface.

Watch out

The Clemmensen reduction only works for aldehydes and ketones. It does not reduce carboxylic acids, esters, or amides — those require different conditions (like LiAlH₄). Also, the reaction requires strong acid, so any functional group that is acid-sensitive (like an alcohol or an alkene) will be destroyed.

When to Use It — and When Not To

The Clemmensen reduction is a classic method, but it has a major limitation: the strongly acidic conditions. If your molecule contains an acid-sensitive group (a tertiary alcohol, an acetal, a double bond that might rearrange), this reaction will ruin it.

For those cases, you use the Wolff-Kishner reduction instead — that uses hydrazine and strong base, so it works under basic conditions. The two reactions are complementary: Clemmensen for acid-stable substrates, Wolff-Kishner for base-stable ones. …

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(i) Clemmensen reduction turns propanone's carbonyl into a CH₂, giving propane; (ii) the Stephen reaction reduces benzonitrile's –CN to –CHO, giving benzaldehyde.

(i) Clemmensen reduction of propan-2-one:

Clemmensen reduction uses zinc amalgam (Zn–Hg) with concentrated HCl and reduces a carbonyl group ( $>C=O$ ) all the way to a methylene group ( $-CH_2-$ ).

$CH_3-CO-CH_3 \xrightarrow{\;Zn(Hg)/\text{conc. }HCl\;} CH_3-CH_2-CH_3$

Product: propane.

(ii) Stephen reaction of benzonitrile: …

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Same / Similar Concept — real previous-year questions on the same or a closely similar concept, not this exact question.

CBSE 2026Set ANNUAL1 markMCQ
$Q. In Clemmensen reduction, carbonyl compound is reduced in the presence of$
(a) Zn-Hg + HCl
(b) Na + C2H5OH
(c) Zn-Hg + HNO3
(d) Na + dry ether
›Reveal solutionSolution

Clemmensen reduction converts an aldehyde or ketone's C=O group completely to CH2 using zinc amalgam and concentrated hydrochloric acid.

In the Clemmensen reduction, the carbonyl compound (aldehyde or ketone) is refluxed with zinc amalgam (Zn-Hg) and concentrated HCl:

R2C=O --(Zn-Hg / conc. HCl)--> R2CH2

…

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CBSE 2024Set ANNUAL1 markMCQ
$Q. In Clemmensen reduction, carbonyl compound is reacted with$
(a) Zinc amalgam + HCl
(b) Sodium amalgam + HCl
(c) Zinc amalgam + HNO3
(d) Sodium amalgam + HNO3
›Reveal solutionSolution

Clemmensen reduction is the reagent combination Zn-Hg (zinc amalgam) with concentrated HCl, used to reduce an aldehyde or ketone's C=O group all the way to CH2 (a strongly acidic reduction, unsuitable for acid-sensitive substrates).

R2C=O --(Zn-Hg / conc. HCl)--> R2CH2 + H2O

…

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CBSE 2023Set ANNUAL1 markMCQ
$Q. In Acetaldehyde + 4[H] --(Zn-Hg/HCl)--> A, A is$
(a) Methane
(b) Ethane
(c) Propane
(d) None of these
›Reveal solutionSolution

Zn-Hg amalgam with concentrated HCl is the Clemmensen reduction, which converts an aldehyde/ketone carbonyl (C=O) all the way to CH2, i.e. a hydrocarbon.

CH3CHO + 4[H] --(Zn-Hg/HCl)--> CH3-CH3 + H2O …

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CBSE 2022Set ANNUAL1 mark
$Q. Give the structure of the product expected from the following reaction: 2-butanone is treated with Zn/Hg and conc. HCl.$
›Reveal solutionSolution

Zinc amalgam with concentrated HCl is the classic Clemmensen reduction, which reduces a ketone's carbonyl group all the way down to a methylene ( $-CH_2-$ ) group.

2-Butanone (methyl ethyl ketone, $CH_3-CO-CH_2-CH_3$ ) treated with zinc amalgam ( $Zn/Hg$ ) and concentrated hydrochloric acid undergoes the Clemmensen reduction, which completely deoxygenates the carbonyl carbon, converting $C=O$ directly into $-CH_2-$ :

$CH_3-CO-CH_2-CH_3 \xrightarrow{Zn(Hg)/conc.\,HCl} CH_3-CH_2-CH_2-CH_3$

…

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CBSE 2020Set ANNUAL1 markMCQ
$Q. What products are formed by Clemmensen reduction of Aldehydes?$
(a) Hydrocarbons
(b) Alcohols
(c) Carboxylic acids
(d) Ethers
›Reveal solutionSolution

Clemmensen reduction converts the carbonyl group of an aldehyde or ketone directly into a CH₂ group, giving the corresponding hydrocarbon.

In Clemmensen reduction, an aldehyde or ketone is treated with zinc amalgam (Zn–Hg) and concentrated hydrochloric acid. This reduces the C=O group all the way to CH₂, converting the carbonyl compound into the corresponding alkane (hydrocarbon). It is especially useful for substrates that are stable to strong acid but would be destroyed by other reducing c …

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CBSE 2020Set ANNUAL1 mark
$Q. Identify 'A' in the reaction C=O —(Zn-Hg / HCl)\to A + H₂O .$
›Reveal solutionSolution

Zinc amalgam and conc. HCl (Clemmensen reduction) convert the carbonyl group $>C=O$ into a $>CH_2$ group, so $A = >CH_2$ (a hydrocarbon).

Concept. Aldehydes and ketones can be reduced all the way to hydrocarbons. Clemmensen reduction uses zinc amalgam ( $Zn(Hg)$ ) and concentrated hydrochloric acid to reduce the carbonyl carbon.

Reaction.

$>C=O \xrightarrow{Zn-Hg,\ conc.\ HCl} >CH_2 + H_2O$

The carbonyl oxygen is removed and replaced by two hydrogen atoms, converting $C=O$ into $CH_2$ .

…

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CBSE 2019Set ANNUAL1 markMCQ
$Q. Acetaldehyde + 4[H] --Zn-Hg/HCl--> A. 'A' is$
(a) Methane
(b) Ethane
(c) Propane
(d) none of these.
›Reveal solutionSolution

Zn(Hg)/conc. HCl is the Clemmensen reduction, which reduces an aldehyde or ketone carbonyl completely to a CH2 group (i.e. to the corresponding alkane).

CH3CHO + 4[H] --Zn-Hg/HCl--> CH3-CH3 + H2O

…

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CBSE 2018Set ANNUAL1 markMCQ
$Q. In Clemmensen reduction carbonyl compound is treated with$
(a) Zinc amalgam + HCl
(b) Sodium amalgam + HCl
(c) Zinc amalgam + $HNO_3$
(d) Sodium amalgam + $HNO_3$
›Reveal solutionSolution

Clemmensen reduction converts a carbonyl group directly to $-CH_2-$ using zinc amalgam and concentrated hydrochloric acid.

In the Clemmensen reduction, an aldehyde or ketone's carbonyl group ( $C=O$ ) is completely reduced to a methylene group ( $-CH_2-$ ) by treating it with zinc amalgam ( $Zn(Hg)$ ) and concentrated hydrochloric acid:

$R_2C=O \xrightarrow{Zn(Hg)/HCl} R_2CH_2$ …

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Q.Identify the products of the following named reactions:

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