Aldehydes, Ketones and Carboxylic Acids
31 JEE Chemistry previous year questions on Aldehydes, Ketones and Carboxylic Acids — options free on every question; 3 include the answer & explanation free, the rest unlock with PYQ Pass.
An optically active alkyl halide \({\mathrm{C}}_{4}{\mathrm{H}}_{9}\mathrm{Br}[\mathrm{A}]\) reacts with hot \(\mathrm{KOH}\) dissolved in ethanol and forms alkene [B] as major product which reacts with bromine to give dibromide [C]. The compound [C] is converted into a gas [D] upon reacting with alcoholic \({\mathrm{NaNH}}_{2}\). During hydration 18 gram of water is added to 1 mole of gas [D] on warming with mercuric sulphate and dilute acid at 333 K to form compound [E]. The IUPAC name of compound [ E ] is
[JEE Main 2025, 2 Apr (Shift 1)]
\(\mathrm{Butan}-2-\mathrm{one}\)
Optically active \({\mathrm{C}}_{4}{\mathrm{H}}_{9}\mathrm{Br}\) must be 2-bromobutane.
2-bromobutane + alcoholic KOH → but-2-ene (major)
but-2-ene + \({\mathrm{Br}}_{2}\) → 2,3-dibromobutane
2,3-dibromobutane + alcoholic \(NaN{H}_{2}\)→ but-2-yne (gas)
Hydration of but-2-yne with \(HgS{O}_{4}\) and dilute acid gives a ketone.
Addition of 18 g water (1 mole) confirms ketone formation.
Final product is butan-2-one.
Both acetaldehyde and acetone (individually) undergo which of the following reactions?
A. Iodoform Reaction
B. Cannizzaro Reaction
C. Aldol Condensation
D. Tollen's Test
E. Clemmensen Reduction
Choose the correct answer from the options given below
A, C and E Only
Cannizzaro Reaction:
- Cannizzaro reaction occurs in aldoses (aldehydes with no \(\alpha\)-hydrogen).
- Acetaldehyde \(\left(C{H}_{3}CHO\right)\) has an \(\alpha\)-hydrogen, so it does NOT undergo the Cannizzaro reaction.
- Acetone \(\left(C{H}_{3}COC{H}_{3}\right)\) is a ketone and also does not undergo the Cannizzaro reaction.
Tollen's Test:
- Tollen's test detects aldehydes (it oxidizes them to carboxylic acids).
- Acetaldehyde \(\left(C{H}_{3}CHO\right)\) is an aldehyde, so it gives a positive Tollen's test.
- Acetone \(\left(C{H}_{3}COC{H}_{3}\right)\) is a ketone, and ketones do not give Tollen's test.
Given below are two statements.
Statement I : The dipole moment of \(\overset{4}{{\mathrm{CH}}_{3}-}\overset{3}{\mathrm{CH}}=\overset{2}{\mathrm{CH}}-\overset{1}{\mathrm{CH}}=\mathrm{O}\) is greater than \(\overset{4}{{\mathrm{CH}}_{3}-}\overset{3}{{\mathrm{CH}}_{2}}-\overset{2}{{\mathrm{CH}}_{2}}-\overset{1}{\mathrm{CH}}=\mathrm{O}\)
Statement II : \({\mathrm{C}}_{1}-{\mathrm{C}}_{2}\) bond length of is \(\underset{4}{{\mathrm{CH}}_{3}-}\underset{3}{\mathrm{CH}}\underset{2}{=\mathrm{CH}-}\underset{1}{\mathrm{CH}}=\mathrm{O}\) greater than \({\mathrm{C}}_{1}-{\mathrm{C}}_{2}\) bond length of \(\underset{4}{{\mathrm{CH}}_{3}-}\underset{3}{{\mathrm{CH}}_{2}}\underset{2}{-{\mathrm{CH}}_{2}-}\underset{1}{\mathrm{CH}}=\mathrm{O}\)
In the light of the above statements, choose the correct answer from the options given below:
[JEE Main 2025, 4 Apr (Shift 1)]
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Consider the following sequence of reaction\({\mathrm{C}}_{6}{\mathrm{H}}_{12}\overset{\mathrm{Se}/∆}{\to }\mathrm{A}\overset{{\mathrm{CH}}_{3}-\mathrm{Cl}}{\underset{{\mathrm{AlCl}}_{3}}{\to }}\mathrm{B}\overset{{\mathrm{CrO}}_{2}{\mathrm{Cl}}_{2}}{\underset{{{\mathrm{H}}_{3}\mathrm{O}}^{+}}{\to }}\mathrm{C}\)
Choose the correct option about maior product
Memory Based Question 28/Jan/25 Evening shift
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Consider the following sequence of reaction\({\mathrm{C}}_{6}{\mathrm{H}}_{12}\overset{\mathrm{Se}/∆}{\to }\mathrm{A}\overset{{\mathrm{CH}}_{3}-\mathrm{Cl}}{\underset{{\mathrm{AlCl}}_{3}}{\to }}\mathrm{B}\overset{{\mathrm{CrO}}_{2}{\mathrm{Cl}}_{2}}{\underset{{{\mathrm{H}}_{3}\mathrm{O}}^{+}}{\to }}\mathrm{C}\)
Choose the correct option about maior product
Memory Based Question 28/Jan/25 Evening shift
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Number of molecules from below which cannot give iodoform reaction is
Ethanol, Isopropyl alcohol, Bromoacetone, 2-Butanol, 2-Butanone, Butanal, 2-Pentanone, 3-Pentanone, Pentanal and 3-Pentanol
[JEE Main 2025, 3 Apr (Shift 1)]
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\({\mathrm{CH}}_{3}-\mathrm{C}\equiv \mathrm{CH}\overset{\mathrm{Pd}/\mathrm{C}}{\underset{{\mathrm{H}}_{2}}{\to }}\mathrm{A}\overset{(\mathrm{i}){\mathrm{O}}_{3}}{\underset{(\mathrm{ii})\mathrm{Zn},{\mathrm{H}}_{2}\mathrm{O}}{\to }}\mathrm{B}+\mathrm{C}\)
Products B and C are :
Memory Based Question 28/Jan/25 Evening shift
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An optically active alkyl halide \({\mathrm{C}}_{4}{\mathrm{H}}_{9}\mathrm{Br}[\mathrm{A}]\) reacts with hot \(\mathrm{KOH}\) dissolved in ethanol and forms alkene [B] as major product which reacts with bromine to give dibromide [C]. The compound [C] is converted into a gas [D] upon reacting with alcoholic \({\mathrm{NaNH}}_{2}\). During hydration 18 gram of water is added to 1 mole of gas [D] on warming with mercuric sulphate and dilute acid at 333 K to form compound [E]. The IUPAC name of compound [ E ] is
[JEE Main 2025, 2 Apr (Shift 1)]
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Both acetaldehyde and acetone (individually) undergo which of the following reactions,
A) lodoform Reaction
B) Cannizzaro Reaction
C) Aldol condensation.
D) Tollen's test
E) Clemmesen Reduction
Memory Based Question 28/Jan/25 Morning shift
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Both acetaldehyde and acetone (individually) undergo which of the following reactions?
A. Iodoform Reaction
B. Cannizzaro Reaction
C. Aldol Condensation
D. Tollen's Test
E. Clemmensen Reduction
Choose the correct answer from the options given below
[JEE Main 2025, 28 Jan (Shift 1)]
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Which is the correct order of nucleophilic addition
1. Acetophenone,
2. p-nitrobenzaldehyde
3. benzaldehyde,
4. p-tolualdehyde
(Memory Based JEE Mains 24/01/2025 ,Shift -1)
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Grignard reagent RMgBr (P) reacts with water and forms a gas (Q). One gram of Q occupies 1.4 dm3 at STP. (P) on reaction with dry ice in dry ether followed by H3O+ forms a compound (Z). 0.1 mole of (Z) will weigh g. (Nearest integer)
[JEE Main 2026, 24 Jan (Shift 2)]
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Which of the following arrangements with respect to their reactivity in nucleophilic addition reaction is correct?
[JEE Main 2025, 24 Jan (Shift 1)]
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Grignard reagent RMgBr (P) reacts with water and forms a gas (Q). One gram of Q occupies 1.4 dm3 at STP. (P) on reaction with dry ice in dry ether followed by H3O+ forms a compound (Z). 0.1 mole of (Z) will weigh g. (Nearest integer)
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Both acetaldehyde and acetone (individually) undergo which of the following reactions,
A) lodoform Reaction
B) Cannizzaro Reaction
C) Aldol condensation.
D) Tollen's test
E) Clemmesen Reduction
Memory Based Question 28/Jan/25 Morning shift
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Given below are two statements:
Statement I: Cross aldol condensation between two different aldehydes will always produce four different products.
Statement II: When semicarbazide reacts with a mixture of benzaldehyde and acetophenone under optimum pH, it forms a condensation product with acetophenone only.
In the light of the above statements, choose the correct answer from the options given below
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Given below are two statements:
Statement I: Cross aldol condensation between two different aldehydes will always produce four different products.
Statement II: When semicarbazide reacts with a mixture of benzaldehyde and acetophenone under optimum pH, it forms a condensation product with acetophenone only.
In the light of the above statements, choose the correct answer from the options given below
[JEE Main 2026, 24 Jan (Shift 2)]
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Which is the correct order of nucleophilic addition
1. Acetophenone,
2. p-nitrobenzaldehyde
3. benzaldehyde,
4. p-tolualdehyde
(Memory Based JEE Mains 24/01/2025 ,Shift -1)
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Which of the following arrangements with respect to their reactivity in nucleophilic addition reaction is correct?
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Number of molecules from below which cannot give iodoform reaction is
Ethanol, Isopropyl alcohol, Bromoacetone, 2-Butanol, 2-Butanone, Butanal, 2-Pentanone, 3-Pentanone, Pentanal and 3-Pentanol
[JEE Main 2025, 3 Apr (Shift 1)]
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\({\mathrm{CH}}_{3}-\mathrm{C}\equiv \mathrm{CH}\overset{\mathrm{Pd}/\mathrm{C}}{\underset{{\mathrm{H}}_{2}}{\to }}\mathrm{A}\overset{(\mathrm{i}){\mathrm{O}}_{3}}{\underset{(\mathrm{ii})\mathrm{Zn},{\mathrm{H}}_{2}\mathrm{O}}{\to }}\mathrm{B}+\mathrm{C}\)
Products B and C are :
Memory Based Question 28/Jan/25 Evening shift
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An organic compound \(\mathbf{P}\) having molecular formula \({\mathrm{C}}_{6}{\mathrm{H}}_{6}{\mathrm{O}}_{3}\) gives ferric chloride test and does not have intramolecular hydrogen bond. The compound \(\mathbf{P}\) reacts with 3 equivalents of \({\mathrm{NH}}_{2}\mathrm{OH}\) to produce oxime Q. Treatment of \(\mathbf{P}\) with excess methyl iodide in the presence of \(\mathrm{KOH}\) produces compound \(\mathbf{R}\) as the major product. Reaction of \(\mathbf{R}\) with excess iso-butylmagnesium bromide followed by treatment with \({\mathrm{H}}_{3}{\mathrm{O}}^{+}\)gives compound \(S\) as the major product.
The total number of methyl \(\left(-{\mathrm{CH}}_{3}\right)\) group(s) in compound \(S\) is _____ .
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The increasing order of the reactivity of the following compounds in nucleophilic addition reaction is Propanal, Benzaldehyde, Propanone, Butanone
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Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R):
Assertion (A): Acetal/Ketal is stable in basic medium.
Reason (R): The high leaving tendency of alkoxide ion gives the stability to acetal/ketal in basic medium.
In the light of the above statements, choose the correct answer from the options given below:
[JEE Main 2023, 25 Jan (Shift 1)]
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In Tollen's test for aldehyde, the overall number of electron(s) transferred to the Tollen's reagent formula \({\left[\mathrm{Ag}{\left({\mathrm{NH}}_{3}\right)}_{2}\right]}^{+}\) per aldehyde group to form silver mirror is ____. (Round off to the nearest integer).
[JEE Main 2021, 18 Mar (Shift 2)]
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Which one of the following reactions will not yield propionic acid?
[JEE Main 2021, 27 Aug (Shift 2)]
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\(R—C\equiv N\overset{DIBAL-H}{\underset{{H}_{2}O}{\to }}R—Y\)
Consider the above reaction and identify \( Y \)
[JEE Main 2021, 27 Jul (Shift 2)]
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Match List-I with List-II.
| List-I (Test) | List-II (Identification) | ||
| (A) | Bayer's test | (I) | Phenol |
| (B) | Ceric ammonium nitrate test | (II) | Aldehyde |
| (C) | Phthalein dye test | (III) | Alcoholic-OH group |
| (D) | Schiff's test | (IV) | Unsaturtion |
Choose the correct answer from the options given below:
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In the reaction of hypobromite with amide, the carbonyl carbon is lost as:
[JEE Main 2021, 18 Mar (Shift 2)]
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2,4-DNP test can be used to identify
[JEE Main 2021, 26 Feb (Shift 2)]
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