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Aldehydes/ketones: carbonyl chemistry and named reactions: NEET MCQs with answers

49 questions on this topic of Organic Compounds Containing Oxygen (NEET 2027 syllabus). Here are 12; tap one to see its answer and explanation.

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easy

1. Dry distillation of a mixture containing calcium acetate and calcium formate yields which major organic carbonyl compound?

  1. Propanone
  2. Ethanal
  3. Methanal
  4. Pentan-3-one
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Answer: (B) Ethanal

Dry distillation of calcium formate alone yields methanal, and calcium acetate alone yields propanone. When an equimolar mixture of calcium acetate, (CH₃COO)₂Ca, and calcium formate, (HCOO)₂Ca, is distilled, the cross-product ethanal (CH₃CHO) is obtained along with CaCO₃.

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2. Given below are two statements: Statement I: Carboxylic acids do not form addition compounds with sodium hydrogen sulphite (NaHSO₃). Statement II: The resonance stabilization of the carboxylate group and resonance donation from the -OH group significantly reduce the electrophilicity of the carbonyl carbon in carboxylic acids. In the light of the above statements, choose the most appropriate answer:

  1. Both Statement I and Statement II are correct
  2. Statement I is correct but Statement II is incorrect
  3. Statement I is incorrect but Statement II is correct
  4. Both Statement I and Statement II are incorrect
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Answer: (A) Both Statement I and Statement II are correct

In carboxylic acids, resonance donation from the lone pair of the hydroxyl oxygen into the carbonyl carbon greatly decreases its positive character compared to aldehydes and ketones. Consequently, carboxylic acids do not undergo characteristic nucleophilic additions like forming NaHSO₃ bisulphite adducts.

hard

3. Identify the correct structure of the 2,4-DNP derivative formed when cyclopentanone reacts with 2,4-dinitrophenylhydrazine under acidic conditions:

  1. Cyclopentyl-2,4-dinitrophenyl ether
  2. Cyclopentylhydrazine
  3. 1-(2,4-Dinitrophenyl)cyclopentanol
  4. Cyclopentylidene-(2,4-dinitrophenyl)hydrazine
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Answer: (D) Cyclopentylidene-(2,4-dinitrophenyl)hydrazine

The reaction of cyclopentanone with 2,4-dinitrophenylhydrazine (Brady's reagent) is a nucleophilic addition followed by elimination of a water molecule, forming a hydrazone named cyclopentylidene-(2,4-dinitrophenyl)hydrazine.

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4. What is the major organic product formed when benzaldehyde is treated with concentrated nitric acid and concentrated sulphuric acid at 273–283 K?

  1. 4-Nitrobenzaldehyde
  2. 3-Nitrobenzaldehyde
  3. 2-Nitrobenzaldehyde
  4. 2,4-Dinitrobenzaldehyde
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Answer: (B) 3-Nitrobenzaldehyde

The aldehyde group (-CHO) on a benzene ring is strongly deactivating and meta-directing due to its electron-withdrawing nature via resonance and inductive effects. Electrophilic aromatic substitution (nitration) occurs predominantly at the meta position, giving 3-nitrobenzaldehyde.

easy

5. Reaction of an aldehyde with one equivalent of a monohydric alcohol in the presence of dry hydrogen chloride gas yields:

  1. A hemiacetal
  2. An acetal
  3. A cyclic ketal
  4. An ester
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Answer: (A) A hemiacetal

Aldehydes react with one equivalent of a monohydric alcohol in the presence of dry HCl gas to yield alkoxyalcohol intermediate known as a hemiacetal. Reaction with another equivalent of alcohol produces a gem-dialkoxy compound termed an acetal.

hard

6. An organic compound 'X' (C₄H₈O) does not reduce Fehling's solution and does not form an addition compound with NaHSO₃, but on treatment with I₂/NaOH gives a yellow solid and a carboxylic acid salt 'Y'. Acidification of 'Y' gives:

  1. Propanoic acid
  2. Ethanoic acid
  3. Methanoic acid
  4. Butanoic acid
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Answer: (A) Propanoic acid

Compound 'X' is a ketone that gives a positive iodoform test, so it must be butan-2-one (CH₃COCH₂CH₃). It does not react with NaHSO₃ easily due to steric factors and does not reduce Fehling's solution. Cleavage during the haloform reaction gives CHI₃ and sodium propanoate ('Y'). Acidification of 'Y' yields propanoic acid.

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7. Aldehydes are generally more reactive than ketones towards nucleophilic addition because:

  1. Ketones are more polar
  2. Aldehydes are saturated
  3. Ketones have two alkyl groups that cause steric hindrance and reduce the electrophilicity of the carbonyl carbon
  4. Aldehydes have no carbonyl group
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Answer: (C) Ketones have two alkyl groups that cause steric hindrance and reduce the electrophilicity of the carbonyl carbon

Two electron-releasing alkyl groups in ketones reduce the positive charge on carbonyl carbon and hinder nucleophilic attack sterically.

NCERT Class 12

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8. Aldehydes without an α-hydrogen, such as HCHO and benzaldehyde, with concentrated alkali undergo:

  1. Cannizzaro reaction (self oxidation-reduction)
  2. Aldol condensation
  3. Wolff-Kishner reduction
  4. Etard reaction
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Answer: (A) Cannizzaro reaction (self oxidation-reduction)

In the Cannizzaro reaction one molecule is reduced to the alcohol and another oxidised to the carboxylate salt.

NCERT Class 12

hard

9. When cyclohexanone is treated with pyrrolidine in the presence of a trace of acid and azeotropic removal of water, compound P is formed. Subsequent reaction of P with ethyl iodide followed by aqueous acidic hydrolysis yields:

  1. Ethyl cyclohexanecarboxylate
  2. 1-Ethylcyclohexanone
  3. 2,2-Diethylcyclohexanone
  4. 2-Ethylcyclohexanone
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Answer: (D) 2-Ethylcyclohexanone

Cyclohexanone reacts with pyrrolidine (a secondary amine) to yield an enamine (compound P). Enamines act as nucleophiles at the α-carbon. Alkylation with ethyl iodide introduces an ethyl group at the C-2 position. Subsequent acidic hydrolysis regenerates the carbonyl group, yielding 2-ethylcyclohexanone (Stork enamine synthesis).

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10. When an equimolar mixture of formaldehyde (HCHO) and benzaldehyde (C₆H₅CHO) is heated with concentrated NaOH solution, the major products formed are:

  1. Sodium benzoate and methanol
  2. Sodium benzoate and sodium formate
  3. Benzyl alcohol and formic acid
  4. Sodium formate and benzyl alcohol
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Answer: (D) Sodium formate and benzyl alcohol

In a crossed Cannizzaro reaction involving formaldehyde, OH⁻ preferentially attacks the more electrophilic and sterically unhindered carbonyl carbon of HCHO. Consequently, formaldehyde is oxidized to sodium formate, and benzaldehyde is reduced to benzyl alcohol.

easy

11. What is the major organic product obtained when 2,2-dimethylpropanal is heated with excess concentrated KOH solution?

  1. 2,2-Dimethylbutane and carbon dioxide
  2. 3-Hydroxy-2,2,4,4-tetramethylpentanal
  3. 2,2-Dimethylpropanoic acid and 2,2-dimethylpropan-1-ol
  4. Pivalic anhydride and water
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Answer: (C) 2,2-Dimethylpropanoic acid and 2,2-dimethylpropan-1-ol

2,2-Dimethylpropanal [(CH₃)₃C-CHO] lacks α-hydrogens, so it undergoes the Cannizzaro reaction on heating with concentrated KOH. Disproportionation gives potassium 2,2-dimethylpropanoate (which on acidification yields 2,2-dimethylpropanoic acid) and 2,2-dimethylpropan-1-ol.

easy

12. Which of the following compounds will react with a Grignard reagent (CH₃MgBr) followed by acidic hydrolysis to give a tertiary alcohol?

  1. Methanal
  2. Ethanal
  3. Propan-2-one
  4. Propanal
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Answer: (C) Propan-2-one

Reaction of a ketone with a Grignard reagent yields a tertiary alcohol after hydrolysis. Formaldehyde yields primary alcohols, and all other aldehydes yield secondary alcohols. Propan-2-one is a ketone and therefore gives 2-methylpropan-2-ol, a tertiary alcohol.

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