JEE Chemistry Aldehydes Ketones and Carboxylic Acids MCQs Set 07

Multiple Choice Questions (MCQs) for JEE Chemistry: Aldehydes Ketones and Carboxylic Acids

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Multiple Choice Questions

Question 1: Which of the following on treatment with 50% aqueous NaOH yields the corresponding alcohol and acid?
(a) \( \ce{C6H5CHO} \)
(b) \( \ce{CH3CH2CH2CHO} \)
(c) \( \ce{CH3COCH3} \)
(d) \( \ce{CH3CHO} \)
Show Answer & Explanation

Answer: (a) \( \ce{C6H5CHO} \)

Explanation:
1. Only benzaldehyde has no alpha hydrogen and undergoes the Cannizzaro reaction.
2. Others have alpha-H and give aldol reactions.

Teacher's Note:
1. Cannizzaro: both an alcohol and an acid salt form.

Question 2: Ethanol heated with acetic acid in the presence of a few drops of conc. sulphuric acid gives the smell of:
(a) oil of wintergreen
(b) oil of mustard
(c) an ester (fruity smell)
(d) oil of bitter almonds
Show Answer & Explanation

Answer: (c) an ester (fruity smell)

Explanation:
1. Fischer esterification gives ethyl acetate, which has a fruity smell.

Teacher's Note:
1. Esters are responsible for fruit flavours.

Question 3: A carbonyl compound gives a pink colour with Schiff's reagent and a yellow precipitate when boiled with iodine and caustic alkali. It also gives a red precipitate with Fehling's solution. It is likely to be:
(a) formaldehyde
(b) propionaldehyde
(c) acetaldehyde
(d) crotonaldehyde
Show Answer & Explanation

Answer: (c) acetaldehyde

Explanation:
1. Schiff's and Fehling's tests show an aldehyde, and iodoform shows a \( \ce{CH3CO-} \) unit.
2. Acetaldehyde fulfils all three.

Teacher's Note:
1. Acetaldehyde is the only aldehyde that gives iodoform.

Question 4: A carbonyl compound gives a positive iodoform test but does not reduce Tollens' reagent or Fehling's solution. It forms a cyanohydrin whose hydrolysis gives a hydroxy acid with a methyl side chain. The compound is:
(a) acetaldehyde
(b) propionaldehyde
(c) acetone
(d) crotonaldehyde
Show Answer & Explanation

Answer: (c) acetone

Explanation:
1. No reduction of Tollens' shows it is a ketone, and iodoform shows a methyl ketone.
2. Acetone cyanohydrin hydrolyses to 2-hydroxy-2-methylpropanoic acid, which has methyl side chains.

Teacher's Note:
1. Methyl ketone plus no silver mirror points to acetone.

Question 5: Which of the following statements is wrong?
(a) all methyl ketones give a positive iodoform test
(b) acetaldehyde is the only aldehyde that gives the iodoform test
(c) all secondary alcohols give a positive iodoform test
(d) any alcohol that can be oxidised to an acetyl group gives a positive iodoform test
Show Answer & Explanation

Answer: (c) all secondary alcohols give a positive iodoform test

Explanation:
1. Only secondary alcohols of the type \( \ce{CH3CH(OH)R} \) are positive.
2. Others, such as pentan-3-ol, are negative.

Teacher's Note:
1. The structural requirement is the \( \ce{CH3CH(OH)-} \) group.

Question 6: In the sequence acetone \( \ce{->[I2/alkali] A ->[Ag, heat] B ->[dil. H2SO4, Hg2+] C} \), A, B and C are:
(a) \( \ce{CHI3} \), \( \ce{H2C=CH2} \), \( \ce{CH3CH2OH} \)
(b) \( \ce{CHI3} \), \( \ce{HC#CH} \), \( \ce{CH3CHO} \)
(c) \( \ce{CHI3} \), \( \ce{CH3C#CH} \), \( \ce{CH3COCH3} \)
(d) \( \ce{CHI3} \), \( \ce{CH3CH(OH)CH3} \), \( \ce{CH3COCH3} \)
Show Answer & Explanation

Answer: (b) \( \ce{CHI3} \), \( \ce{HC#CH} \), \( \ce{CH3CHO} \)

Explanation:
1. Acetone with iodine and alkali gives iodoform (A).
2. Silver removes iodine from iodoform to give ethyne (B).
3. Hydration of ethyne with Hg2+ gives acetaldehyde (C).

Teacher's Note:
1. Iodoform plus silver gives acetylene.

Question 7: In the sequence \( \ce{RCOCl + H2 ->[Pd-BaSO4] A ->[HCN] B ->[H3O+] C} \), A, B and C are:
(a) \( \ce{RCHO} \), \( \ce{RCH(OH)CN} \), \( \ce{RCH(OH)CH2NH2} \)
(b) \( \ce{RCHO} \), \( \ce{RCH(OH)CN} \), \( \ce{RCH(OH)COOH} \)
(c) \( \ce{RCHO} \), \( \ce{RCOCH2CN} \), \( \ce{RCOCH2COOH} \)
(d) \( \ce{RCHO} \), \( \ce{RCH2CN} \), \( \ce{RCH2COOH} \)
Show Answer & Explanation

Answer: (b) \( \ce{RCHO} \), \( \ce{RCH(OH)CN} \), \( \ce{RCH(OH)COOH} \)

Explanation:
1. Rosenmund reduction gives the aldehyde.
2. HCN adds to give the cyanohydrin, and hydrolysis converts the -CN group into -COOH, giving the alpha-hydroxy acid.

Teacher's Note:
1. Cyanohydrin hydrolysis gives alpha-hydroxy acids.

Question 8: In the sequence \( \ce{CH3C#CH ->[dil. H2SO4, Hg2+] A ->[CHCl3] B} \) and A with \( \ce{I2/NaOH} \) gives C. A, B and C are:
(a) \( \ce{CH3CH2CHO} \), \( \ce{CH3CH2CH2Cl} \), \( \ce{CHI3} \)
(b) \( \ce{CH3COCH3} \), \( \ce{CCl3-CO-CH3} \), \( \ce{CHI3} \)
(c) \( \ce{CH3COCH3} \), \( \ce{CCl3-C(OH)(CH3)2} \), \( \ce{CHI3} \)
(d) \( \ce{CH3CH2CHO} \), \( \ce{CCl3-CH(OH)-CH2CH3} \), \( \ce{CHI3} \)
Show Answer & Explanation

Answer: (c) \( \ce{CH3COCH3} \), \( \ce{CCl3-C(OH)(CH3)2} \), \( \ce{CHI3} \)

Explanation:
1. Markovnikov hydration of propyne gives acetone (A).
2. Acetone adds chloroform in base to give chloretone, \( \ce{CCl3-C(OH)(CH3)2} \) (B).
3. With iodine and alkali it gives iodoform (C).

Teacher's Note:
1. Chloroform adds across C=O of acetone.

Question 9: Match: (i) benzophenone to diphenylmethane, (ii) benzaldehyde to 1-phenylethanol, (iii) cyclohexanone to cyclohexanol, (iv) phenyl benzoate to benzaldehyde with reagents (a) \( \ce{LiAlH4} \), (b) DIBAL-H, (c) Zn(Hg)/conc. HCl, (d) \( \ce{CH3MgBr} \).
(a) (i)-(c), (ii)-(d), (iii)-(a), (iv)-(b)
(b) (i)-(c), (ii)-(d), (iii)-(b), (iv)-(a)
(c) (i)-(d), (ii)-(c), (iii)-(a), (iv)-(b)
(d) (i)-(d), (ii)-(a), (iii)-(c), (iv)-(b)
Show Answer & Explanation

Answer: (a) (i)-(c), (ii)-(d), (iii)-(a), (iv)-(b)

Explanation:
1. Clemmensen reduction (\( \ce{Zn(Hg)/HCl} \)) turns C=O into CH2.
2. A Grignard reagent adds a methyl group to the aldehyde.
3. LiAlH4 reduces the ketone to the alcohol.
4. DIBAL-H partially reduces the ester to the aldehyde.

Teacher's Note:
1. Match the transformation to the reagent type.

Question 10: Methylamine reacts with acetyl chloride and forms:
(a) \( \ce{CH3NH2} \)
(b) \( \ce{CH3NHNa} \)
(c) \( \ce{CH3NHCOCH3} \)
(d) \( \ce{(CH3)2NCOCH3} \)
Show Answer & Explanation

Answer: (c) \( \ce{CH3NHCOCH3} \)

Explanation:
1. The amine nitrogen attacks the acyl chloride to form N-methylacetamide.

Teacher's Note:
1. This is N-acylation.

Question 11: The intermediates formed during the reaction of \( \ce{RCONH2} \) with \( \ce{Br2} \) and KOH are:
(a) \( \ce{RCONHBr} \) and \( \ce{RNCO} \)
(b) \( \ce{RNHCOBr} \) and \( \ce{RNCO} \)
(c) \( \ce{RNH-Br} \) and \( \ce{RCONHBr} \)
(d) \( \ce{RCONBr2} \)
Show Answer & Explanation

Answer: (a) \( \ce{RCONHBr} \) and \( \ce{RNCO} \)

Explanation:
1. The amide is N-brominated to give RCONHBr, and then the rearrangement gives an isocyanate, RNCO.
2. Hydrolysis gives the amine.

Teacher's Note:
1. Isocyanate formation is the key step of Hofmann rearrangement.

Question 12: \( \ce{CH3CH2Cl ->[NaCN] X ->[Ni/H2] Y ->[acetic anhydride] Z} \). Z is:
(a) \( \ce{CH3CH2CH2NHCOCH3} \)
(b) \( \ce{CH3CH2CH2NH2} \)
(c) \( \ce{CH3CH2CH2CONHCH3} \)
(d) \( \ce{CH3CH2CH2CONHCOCH3} \)
Show Answer & Explanation

Answer: (a) \( \ce{CH3CH2CH2NHCOCH3} \)

Explanation:
1. NaCN gives propanenitrile (X), hydrogenation gives propylamine (Y).
2. Acetylation of the amine gives N-propylacetamide (Z).

Teacher's Note:
1. The nitrile adds one carbon.

Question 13: Butanenitrile is hydrolysed with \( \ce{H3O+} \) to give A, which reacts with \( \ce{NH3} \) on heating to give B. B is:
(a) butanoic acid
(b) butanal
(c) butyl isocyanide
(d) butanamide
Show Answer & Explanation

Answer: (d) butanamide

Explanation:
1. Acid hydrolysis of the nitrile gives butanoic acid (A).
2. The ammonium salt on heating loses water to give butanamide (B).

Teacher's Note:
1. Amide forms by dehydration of the ammonium salt.

Question 14: Sodium ethoxide reacted with ethanoyl chloride. The compound produced is:
(a) ethyl chloride
(b) ethyl ethanoate
(c) diethyl ether
(d) 2-butanone
Show Answer & Explanation

Answer: (b) ethyl ethanoate

Explanation:
1. The ethoxide ion replaces chloride at the acyl carbon to give the ester ethyl ethanoate.

Teacher's Note:
1. This is nucleophilic acyl substitution.

Question 15: Trichloroacetaldehyde was subjected to Cannizzaro's reaction using NaOH. The mixture of products contains sodium trichloroacetate and another compound. The other compound is:
(a) 2,2,2-trichloropropanol
(b) chloroform
(c) 2,2,2-trichloroethanol
(d) trichloromethanol
Show Answer & Explanation

Answer: (c) 2,2,2-trichloroethanol

Explanation:
1. Chloral has no alpha-hydrogen, so Cannizzaro disproportionation occurs.
2. One molecule is oxidised to the acid salt and the other is reduced to \( \ce{CCl3CH2OH} \).

Teacher's Note:
1. Reduction product of an aldehyde is the primary alcohol.

Question 16: Acids do not give the characteristic reactions of the C=O group because of:
(a) dimerisation
(b) resonance
(c) cyclic structures
(d) the attached alkyl radical
Show Answer & Explanation

Answer: (b) resonance

Explanation:
1. In a carboxylic acid, the lone pair on the -OH oxygen is delocalised into the C=O group.
2. So the carbonyl carbon is much less electrophilic than in aldehydes and ketones.

Teacher's Note:
1. Resonance reduces the positive charge on carbon.

Question 17: When 23 g of sodium reacts with methyl alcohol, the gas liberated is:
(a) half a mole of hydrogen
(b) one mole of hydrogen
(c) one mole of oxygen
(d) none
Show Answer & Explanation

Answer: (a) half a mole of hydrogen

Explanation:
1. 23 g of sodium is one mole.
2. \( \ce{2CH3OH + 2Na -> 2CH3ONa + H2} \), so one mole of Na gives half a mole of \( \ce{H2} \).

Teacher's Note:
1. Use the balanced equation.

Question 18: Which of the following compounds are capable of reacting with Tollens' reagent?
(a) formaldehyde
(b) formic acid
(c) acetaldehyde
(d) all of the above
Show Answer & Explanation

Answer: (d) all of the above

Explanation:
1. Formaldehyde and acetaldehyde are aldehydes.
2. Formic acid also has an aldehydic -CHO group and is oxidised.

Teacher's Note:
1. Formic acid is a reducing acid.

Question 19: Fehling's solution is:
(a) a solution of magenta dye bleached by \( \ce{SO2} \)
(b) an ammoniacal solution of \( \ce{AgNO3} \)
(c) a mixture of \( \ce{CuSO4} \) solution and a solution of NaOH and sodium potassium tartrate
(d) an alcoholic solution of 2,4-dinitrophenylhydrazine
Show Answer & Explanation

Answer: (c) a mixture of \( \ce{CuSO4} \) solution and a solution of NaOH and sodium potassium tartrate

Explanation:
1. Fehling's A is aqueous CuSO4 and Fehling's B is alkaline sodium potassium tartrate; they are mixed before use.

Teacher's Note:
1. Tartrate keeps Cu(II) in solution as a complex.

Question 20: Alkanoic acids can be made by hydrolysis of:
(a) trihaloalkanes
(b) 1,1,1-trihaloalkanes
(c) Grignard reagents
(d) ketones
Show Answer & Explanation

Answer: (b) 1,1,1-trihaloalkanes

Explanation:
1. Hydrolysis of RCX3 forms an unstable triol that loses water to give RCOOH.

Teacher's Note:
1. Three halogens on one carbon become an acid group.

Question 21: Acids have much higher boiling points than isomeric esters because:
(a) acids form dimers by H-bonding
(b) acids are volatile in steam
(c) esters are non-volatile
(d) acids can ionise to give protons in aqueous solution
Show Answer & Explanation

Answer: (a) acids form dimers by H-bonding

Explanation:
1. Carboxylic acids form hydrogen-bonded dimers while esters have no O-H group.

Teacher's Note:
1. H-bonding raises the boiling point.

Question 22: The reaction of ethyl acetate with sodium ethoxide to give acetoacetic ester is known as:
(a) Claisen condensation
(b) Clemmensen reduction
(c) Cannizzaro reaction
(d) Etard reaction
Show Answer & Explanation

Answer: (a) Claisen condensation

Explanation:
1. The ester enolate attacks another ester molecule and loses ethoxide to give a beta-keto ester.
2. This is Claisen condensation.

Teacher's Note:
1. Claisen condensation: ester + ester gives beta-keto ester.

Question 23:
Assertion (A): Acetamide on reaction with \( \ce{Br2} \)/NaOH gives \( \ce{CH3NH2} \).
Reason (R): The carbon of the amide functional group becomes part of \( \ce{Na2CO3} \).
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation

Answer: (a) Both A and R are true, and R is the correct explanation of A.

Explanation:
1. In Hofmann degradation the carbonyl carbon is lost as carbonate.
2. This is why the amine has one carbon less. R explains A.

Teacher's Note:
1. Carbonyl carbon leaves as \( \ce{CO3^2-} \).

Question 24:
Assertion (A): Ethyl acetoacetate forms butane-1,4-diol with \( \ce{NaBH4} \).
Reason (R): \( \ce{NaBH4} \) can reduce ketone and ester groups.
(a) Both A and R are true, and R is the correct explanation of A.
(b) Both A and R are true, but R is not the correct explanation of A.
(c) A is true, but R is false.
(d) A is false, but R is true.
Show Answer & Explanation

Answer: (d) A is false, but R is true.

Explanation:
1. NaBH4 reduces only the ketone group, giving ethyl 3-hydroxybutanoate.
2. It does not reduce esters, so both statements are false.

Teacher's Note:
1. LiAlH4 is needed to reduce esters.

Practice MCQs for JEE Chemistry Aldehydes Ketones and Carboxylic Acids

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