CBSE Class 12 Chemistry Aldehydes Ketones and Carboxylic Acids MCQs Set 10

Download CBSE MCQs for Class 12 Chemistry: Unit 8 Aldehydes Ketones and Carboxylic Acids

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Chapter-wise Objective Questions: Unit 8 Aldehydes Ketones and Carboxylic Acids

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Multiple Choice Questions

Question 1: Ketones (R–CO–R′) can be obtained in one step by (where R and R′ are alkyl groups)
(a) hydrolysis of esters
(b) oxidation of primary alcohols
(c) oxidation of secondary alcohols
(d) reaction of alkyl halides with alcohols.
Show Answer & Explanation

Answer: (c) oxidation of secondary alcohols

Explanation:
1. Ketones are formed by oxidation of secondary alcohols.
2. CH3–CH(OH)–CH3 [O]
⟶
CH3–CO–CH3

Teacher's Note:
1. Primary alcohols oxidise to aldehydes (and then acids); only secondary alcohols stop at the ketone stage.

Question 2: Aldehydes other than formaldehyde react with Grignard’s reagent to give addition products which on hydrolysis give
(a) tertiary alcohols
(b) secondary alcohols
(c) primary alcohols
(d) carboxylic acids.
Show Answer & Explanation

Answer: (b) secondary alcohols

Explanation:
1. Formaldehyde forms primary alcohol while all other aldehydes form secondary alcohols on reaction with Grignard’s reagent followed by hydrolysis.
2. CH3CHO + CH3MgI → (CH3)(H)C(OMgI)CH3 H+/H2O
⟶
CH3–CH(OH)–CH3 + Mg(OH)I

Teacher's Note:
1. Remember the pattern: HCHO gives 1° alcohol, other aldehydes give 2° alcohols and ketones give 3° alcohols with RMgX.

Question 3: Propanal on treatment with dilute sodium hydroxide gives
(a) CH3CH2CH2CH2CH2CHO
(b) CH3CH2CH(OH)CH2CH2CHO
(c) CH3CH2CH(OH)CH(CH3)CHO
(d) CH3CH2COOH
Show Answer & Explanation

Answer: (c) CH3CH2CH(OH)CH(CH3)CHO

Explanation:
1. CH3CH2CHO + CH3CH2CHO dil. NaOH
⟶
CH3–CH2–CH(OH)–CH(CH3)–CHO
2. The α-carbon (CH2) of one propanal molecule attacks the carbonyl carbon of the other, so the CH3 ends up as a branch on the α-carbon.

Teacher's Note:
1. In an aldol product the new C–C bond is always between the α-carbon of one molecule and the carbonyl carbon of the other.

Question 4: Various products formed on oxidation of 2,5-dimethylhexan-3-one are
(i) CH3–CH(CH3)–COOH
(ii) CH3–CH(CH3)–CH2–COOH
(iii) CH3COOH
(iv) HCOOH
(a) (i) and (iii)
(b) (i), (ii) and (iii)
(c) (i), (ii), (iii) and (iv)
(d) (iii) and (iv)
Show Answer & Explanation

Answer: (c) (i), (ii), (iii) and (iv)

Explanation:
1. (CH3)2CH–CO–CH2–CH(CH3)2 [O]
⟶
CH3–CH(CH3)–COOH + CH3–CH(CH3)–CH2–COOH + CH3–CO–CH3
2. The CH3–CO–CH3 formed is further oxidised: CH3COCH3 → HCOOH + CH3COOH
3. So all four products (i), (ii), (iii) and (iv) are formed.

Teacher's Note:
1. Strong oxidation of a ketone breaks the C–CO bond on either side, so check both possible cleavages before choosing.

Question 5: Alkene (X) (C5H10) on ozonolysis gives a mixture of two compounds (Y) and (Z). Compound (Y) gives positive Fehling’s test and iodoform test. Compound (Z) does not give Fehling’s test but give iodoform test. Compounds (X), (Y) and (Z) are
XYZ
(a)C6H5COCH3CH3CHOCH3COCH3
(b)CH3–CH=C(CH3)–CH3CH3CHOCH3COCH3
(c)CH3CH2CH=CH2CH3CH2CHOHCHO
(d)CH3–CH=CH–CH3CH3CHOCH3CHO

(a) (a)
(b) (b)
(c) (c)
(d) (d)
Show Answer & Explanation

Answer: (b) (b)

Explanation:
1. CH3–CH=C(CH3)–CH3 (X) (i) O3
⟶
(ii) Zn/H2O
CH3CHO (Y) + CH3–CO–CH3 (Z)
2. CH3CHO gives positive Fehling’s test and iodoform test; CH3COCH3 gives only the iodoform test.

Teacher's Note:
1. Work backwards from ozonolysis: join the two carbonyl carbons by a C=C to rebuild the alkene.

Question 6: A compound (X) with a molecular formula C5H10O gives a positive 2,4-DNP test but a negative Tollen’s test. On oxidation it gives a carboxylic acid (Y) with a molecular formula C3H6O2. Potassium salt of (Y) undergoes Kolbe’s reaction and gives a hydrocarbon (Z). (X), (Y) and (Z) respectively are
(a) pentan-3-one, propanoic acid, butane
(b) pentanal, pentanoic acid, octane
(c) 2-methylbutanone, butanoic acid, hexane
(d) 2, 2-dimethylpropanone, propanoic acid, hexane
Show Answer & Explanation

Answer: (a) pentan-3-one, propanoic acid, butane

Explanation:
1. Since the compound gives positive 2,4-DNP test and negative Tollen’s test, it is a ketone.
2. CH3CH2–CO–CH2CH3 (pentan-3-one, X) [O]
⟶
2CH3CH2COOH (propanoic acid, Y)
3. CH3CH2COOH KOH
⟶
CH3CH2COOK + H2O; 2CH3CH2COO− Electrolysis
⟶
CH3CH2CH2CH3 (Z) + 2CO2

Teacher's Note:
1. In Kolbe electrolysis two alkyl groups join, so the alkane has twice the carbons of R: C2H5 + C2H5 = butane.

Question 7: Which of the following statements is incorrect?
(a) FeCl3 is used in the detection of phenols.
(b) Fehling solution is used in the detection of glucose.
(c) Tollens’ reagent is used in the detection of unsaturation.
(d) NaHSO3 is used in the detection of carbonyl compounds.
Show Answer & Explanation

Answer: (c) Tollens’ reagent is used in the detection of unsaturation.

Explanation:
1. Tollens’ reagent is used to detect aldehyde group (not unsaturation).

Teacher's Note:
1. Unsaturation is tested with bromine water or Baeyer’s reagent; Tollens’ reagent is specific for the –CHO group.

Question 8: Which of the following compounds will give a coloured crystalline compound with 2,4-dinitrophenylhydrazine, (O2N)2C6H3NHNH2?
(a) CH3COCl
(b) CH3COOC2H5
(c) CH3COCH3
(d) CH3CONH2
Show Answer & Explanation

Answer: (c) CH3COCH3

Explanation:
1. (CH3)2C=O + H2NNH–C6H3(NO2)2 → (CH3)2C=N–NH–C6H3(NO2)2 + H2O
2. Acetone forms the orange-red 2,4-dinitrophenylhydrazone; acid chlorides, esters and amides do not.

Teacher's Note:
1. The C=O of acid derivatives is stabilised by resonance with Cl, OR or NH2, so they do not give the 2,4-DNP test.

Question 9: Which of the following reagents are not correctly matched with the reaction?
(a) CH3CH=CHCHO → CH3CH=CHCOOH : Ammonical AgNO3
(b) CH3CH=CHCHO → CH3CH=CHCH2OH : H2/Pt
(c) R–COOH → R–CH2OH : LiAlH4
(d) CH3CH2COCl → CH3CH2CHO : H2, Pd/BaSO4
Show Answer & Explanation

Answer: (b) CH3CH=CHCHO → CH3CH=CHCH2OH : H2/Pt

Explanation:
1. H2/Pt reduces the C=C bond as well as the –CHO group, so it cannot give CH3CH=CHCH2OH.
2. CH3CH=CHCHO LiAlH4
⟶
CH3CH=CHCH2OH (LiAlH4 or NaBH4 reduces only the carbonyl group).

Teacher's Note:
1. Catalytic hydrogenation is not selective; use LiAlH4 or NaBH4 when the C=C must survive.

Question 10: In the following reaction, product (P) is
R–CO–Cl H2
⟶
Pd/BaSO4
P
(a) RCHO
(b) RCH3
(c) RCOOH
(d) RCH2OH
Show Answer & Explanation

Answer: (a) RCHO

Explanation:
1. Acid chlorides are reduced to aldehydes on reaction with BaSO4 and Pd. The reaction is called Rosenmund reduction.
2. RCOCl H2
⟶
Pd/BaSO4
RCHO + HCl

Teacher's Note:
1. BaSO4 poisons the Pd catalyst so that the aldehyde is not reduced further to an alcohol.

Question 11: Which of the following will not give aldol condensation?
(a) Phenyl acetaldehyde
(b) 2-Methylpentanal
(c) Benzaldehyde
(d) 1-Phenylpropanone
Show Answer & Explanation

Answer: (c) Benzaldehyde

Explanation:
1. Benzaldehyde will not give aldol condensation due to absence of α-H atom.

Teacher's Note:
1. Check the carbon next to C=O: in benzaldehyde it is a ring carbon with no hydrogen.

Question 12: Which of the following statements is correct regarding formic acid?
(a) It is a reducing agent.
(b) It is a weaker acid than acetic acid.
(c) It is an oxidising agent.
(d) When its calcium salt is heated, it forms acetone.
Show Answer & Explanation

Answer: (a) It is a reducing agent.

Explanation:
1. Formic acid acts as a reducing agent: it reduces Fehling’s and Tollen’s reagent, etc.

Teacher's Note:
1. HCOOH contains an aldehyde-like H–C=O unit, which is why it alone among simple acids reduces Tollens’ reagent.

Question 13: The condensation product of benzaldehyde and acetone is
(a) C6H5CH=C(CH3)2
(b) C6H5CH2–CO–CH=CH2
(c) C6H5–CO–CH=CH–CH3
(d) C6H5–CH=CH–CO–CH3
Show Answer & Explanation

Answer: (d) C6H5–CH=CH–CO–CH3

Explanation:
1. C6H5CHO + CH3COCH3 → C6H5–CH(OH)–CH2–CO–CH3 Δ
⟶
–H2O
C6H5–CH=CH–CO–CH3

Teacher's Note:
1. In this cross aldol (Claisen–Schmidt) reaction only acetone has α-hydrogens, so acetone forms the carbanion and benzaldehyde is attacked.

Question 14: Which among the following is most reactive to give nucleophilic addition?
(a) FCH2CHO
(b) ClCH2CHO
(c) BrCH2CHO
(d) ICH2CHO
Show Answer & Explanation

Answer: (a) FCH2CHO

Explanation:
1. FCH2CHO is most reactive towards nucleophilic addition since presence of most electronegative F withdraws electrons from carbon of carbonyl group making it more polar.

Teacher's Note:
1. Electron-withdrawing groups increase the positive charge on the carbonyl carbon; the stronger the –I effect, the faster the nucleophilic addition.

Question 15: Which of the following IUPAC names is not correctly matched?
(a) CH₃COOH : 3-Cyclopentylpropanoic acid
(b) (CH3)2C=CHCOOH : 3-Methylbut-2-enoic acid
(c) PhCH2CH2COOH : 3-Phenylpropanoic acid
(d) COOHNO₂NO₂NO₂ : 2, 4, 6-Trinitrobenzoic acid
Show Answer & Explanation

Answer: (a) CH₃COOH : 3-Cyclopentylpropanoic acid

Explanation:
1. The structure in (a) is 2-methylcyclopentanecarboxylic acid (the –COOH and –CH3 are on adjacent ring carbons), not 3-cyclopentylpropanoic acid.

Teacher's Note:
1. When –COOH is attached directly to a ring, use the suffix ‘carboxylic acid’ and number the ring from that carbon.

Question 16: Which of the following is the most reactive isomer?
(a) CH3CH2CH2CH2–CO–H
(b) CH3CH2CH2–CO–CH3
(c) CH3CH2–CO–CH2CH3
(d) CH3–CO–CH(CH3)–CH3
Show Answer & Explanation

Answer: (a) CH3CH2CH2CH2–CO–H

Explanation:
1. Aldehydes are more reactive than ketones.

Teacher's Note:
1. Aldehydes have one small H on the carbonyl carbon: less steric hindrance and less +I effect than in ketones.

Question 17: The correct order of increasing acidic strength is
(a) Phenol < Ethanol < Chloroacetic acid < Acetic acid
(b) Ethanol < Phenol < Chloroacetic acid < Acetic acid
(c) Ethanol < Phenol < Acetic acid < Chloroacetic acid
(d) Chloroacetic acid < Acetic acid < Phenol < Ethanol
Show Answer & Explanation

Answer: (c) Ethanol < Phenol < Acetic acid < Chloroacetic acid

Explanation:
1. Due to –I effect of Cl, chloroacetic acid is a stronger acid than acetic acid.
2. Due to stabilization of phenoxide ion by resonance, phenol is a stronger acid than ethanol.

Teacher's Note:
1. Carboxylic acids are stronger than phenols because the negative charge of the carboxylate ion is shared equally by two oxygen atoms.

Question 18: To differentiate between pentan-2-one and pentan-3-one a test is carried out. Which of the following is the correct answer?
(a) Pentan-2-one will give silver mirror test
(b) Pentan-2-one will give iodoform test.
(c) Pentan-3-one will give iodoform test
(d) None of these.
Show Answer & Explanation

Answer: (b) Pentan-2-one will give iodoform test.

Explanation:
1. Pentan-2-one will give positive iodoform test while pentan-3-one will not give this test.
2. CH3COCH2CH2CH3 + I2 + NaOH → CHI3 (Iodoform)

Teacher's Note:
1. Only methyl ketones (CH3CO–) give iodoform; pentan-3-one has ethyl groups on both sides.

Question 19: What happens when a carboxylic acid is treated with lithium aluminium hydride?
(a) Aldehyde is formed.
(b) Primary alcohol is formed.
(c) Ketone is formed.
(d) Grignard reagent is formed.
Show Answer & Explanation

Answer: (b) Primary alcohol is formed.

Explanation:
1. RCOOH + 4[H] LiAlH4
⟶
RCH2OH + H2O

Teacher's Note:
1. The aldehyde intermediate is reduced faster than the acid, so LiAlH4 always takes the acid all the way to the 1° alcohol.

Question 20: Which of the following will not undergo HVZ reaction?
(a) Propanoic acid
(b) Ethanoic acid
(c) 2-Methylpropanic acid
(d) 2,2-Dimethylpropanoic acid
Show Answer & Explanation

Answer: (d) 2,2-Dimethylpropanoic acid

Explanation:
1. 2,2-Dimethylpropanoic acid, (CH3)3C–COOH, will not undergo HVZ reaction due to absence of an α-H atom.

Teacher's Note:
1. HVZ needs at least one α-hydrogen; draw the carbon next to –COOH and count its H atoms.

Question 21: When propanal reacts with 2-methylpropanal in presence of NaOH, four different products are formed. The reaction is known as
(a) aldol condensation
(b) cross aldol condensation
(c) Cannizzaro reaction
(d) HVZ condensation.
Show Answer & Explanation

Answer: (b) cross aldol condensation

Explanation:
1. Aldol condensation between two different aldehydes, each having α-hydrogen, is called cross aldol condensation.
2. CH3CH2CHO + (CH3)2CHCHO NaOH
⟶
CH3CH2CH(OH)C(CH3)2CHO + CH3CH2CH=C(CH3)CHO + (CH3)2CHCH(OH)C(CH3)2CHO + (CH3)2CHCH=C(CH3)CHO

Teacher's Note:
1. When both carbonyl compounds have α-hydrogens, cross aldol gives a mixture of four products (two self and two cross).

Question 22: Propanone can be prepared from ethyne by
(a) passing a mixture of ethyne and steam over a catalyst, magnesium at 420°C
(b) passing a mixture of ethyne and ethanol over a catalyst zinc chromite
(c) boiling ethyne with water and H2SO4
(d) treating ethyne with iodine and NaOH.
Show Answer & Explanation

Answer: (a) passing a mixture of ethyne and steam over a catalyst, magnesium at 420°C

Explanation:
1. 2CH≡CH + 3H2O 420°C
⟶
Mg or Zinc vanadate
CH3COCH3 + CO2 + 2H2

Teacher's Note:
1. Hydration of ethyne with dil. H2SO4/HgSO4 gives ethanal, not propanone – a common trap.

Question 23: Match the column I with column II and mark the appropriate choice.
Column IColumn II
(A) RCOCH3 Zn-Hg
⟶
HCl
RCH2CH3
(i) Kolbe’s reaction
(B) 2C6H5CHO NaOH
⟶
C6H5COONa + C6H5CH2OH
(ii) Clemmensen reduction
(C) C6H6 + CH3COCl Anh. AlCl3
⟶
C6H5COCH3
(iii) Friedel–Crafts reaction
(D) C6H5OH + CO2 + NaOH → HOC6H4COONa(iv) Cannizzaro reaction

(a) (A) → (ii), (B) → (iv), (C) → (iii), (D) → (i)
(b) (A) → (i), (B) → (iii), (C) → (ii), (D) → (iv)
(c) (A) → (iii), (B) → (ii), (C) → (i), (D) → (iv)
(d) (A) → (iv), (B) → (i), (C) → (ii), (D) → (iii)
Show Answer & Explanation

Answer: (a) (A) → (ii), (B) → (iv), (C) → (iii), (D) → (i)

Explanation:
1. (A) C=O to CH2 with Zn-Hg/HCl is Clemmensen reduction; (B) disproportionation of benzaldehyde with NaOH is Cannizzaro reaction.
2. (C) acylation of benzene with CH3COCl/AlCl3 is Friedel–Crafts reaction; (D) phenol + CO2 + NaOH giving sodium salicylate is Kolbe’s reaction.

Teacher's Note:
1. Kolbe’s reaction (phenol + CO2) is different from Kolbe electrolysis (carboxylate salts giving alkanes) – read the reaction, not just the name.

Question 24: Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions.
Ethanal, Propanal, Propanone, Butanone
(a) Butanone < Propanone < Propanal < Ethanal
(b) Propanone < Butanone < Ethanal < Propanal
(c) Propanal < Ethanal < Propanone < Butanone
(d) Ethanal < Propanal < Propanone < Butanone
Show Answer & Explanation

Answer: (a) Butanone < Propanone < Propanal < Ethanal

Explanation:
1. Ketones are less reactive than aldehydes.
2. Larger alkyl groups increase the +I effect and steric hindrance, so butanone < propanone and propanal < ethanal.

Teacher's Note:
1. Both size and number of alkyl groups on the carbonyl carbon lower reactivity – rank ketones first, then aldehydes.

Question 25: Which of the following reactions will give benzophenone?
(i) Benzoyl chloride + Benzene + AlCl3
(ii) Benzoyl chloride + Phenylmagnesium bromide
(iii) Benzoyl chloride + Diphenyl cadmium
(a) (i) and (ii)
(b) (ii) and (iii)
(c) (i) and (iii)
(d) (i), (ii) and (iii)
Show Answer & Explanation

Answer: (c) (i) and (iii)

Explanation:
1. (i) C6H5COCl + C6H6 AlCl3
⟶
C6H5–CO–C6H5 + HCl
2. (iii) 2C6H5COCl + (C6H5)2Cd → 2C6H5–CO–C6H5 + CdCl2
3. With phenylmagnesium bromide the ketone formed reacts further to give a tertiary alcohol.

Teacher's Note:
1. Dialkyl/diaryl cadmium is used instead of Grignard reagent because it is less reactive and stops at the ketone.

Question 26: What are the correct steps to convert acetaldehyde to acetone?
(a) CH3MgBr, H2O, Oxidation
(b) Oxidation, Ca(OH)2, Heat
(c) Reduction, KCN, Hydrolysis
(d) Oxidation, C2H5ONa, Heat
Show Answer & Explanation

Answer: (b) Oxidation, Ca(OH)2, Heat

Explanation:
1. CH3CHO K2Cr2O7/H+
⟶
[O]
CH3COOH Ca(OH)2
⟶
(CH3COO)2Ca heat
⟶
CH3COCH3

Teacher's Note:
1. Option (a) also gives acetone (via propan-2-ol), but it adds a carbon through the Grignard step; dry distillation of calcium acetate is the expected route here.

Question 27: Hydrocarbons are formed when aldehydes and ketones are reacted with amalgamated zinc and conc. HCl. The reaction is called
(a) Cannizzaro reaction
(b) Clemmensen reduction
(c) Rosenmund reduction
(d) Wolff-Kishner reduction.
Show Answer & Explanation

Answer: (b) Clemmensen reduction

Explanation:
1. >C=O Zn/Hg
⟶
HCl
>CH2 + H2O is called Clemmensen reduction.

Teacher's Note:
1. Clemmensen uses acid (Zn-Hg/HCl); Wolff–Kishner uses base (NH2NH2/KOH) – choose based on what else the molecule can tolerate.

Question 28: The addition of HCN to carbonyl compounds is an example of
(a) nucleophilic addition
(b) electrophilic addition
(c) free radical addition
(d) electromeric addition.
Show Answer & Explanation

Answer: (a) nucleophilic addition

Explanation:
1. >C=O <→ >C+–O−
2. Nucleophile (CN−) attacks at the positive C centre of carbonyl group hence the addition is nucleophilic addition.

Teacher's Note:
1. The type of addition is named after the species that attacks first – here CN−, a nucleophile.

Question 29: Identify reactant (X) in the given reaction sequence.
CH3COCH3 + X → (CH3)3C–OMgCl H2O
⟶
(CH3)3C–OH + Mg(OH)Cl
(a) CH3MgCl
(b) CH3COCl + Mg
(c) MgCl2
(d) CH3CH2MgCl
Show Answer & Explanation

Answer: (a) CH3MgCl

Explanation:
1. CH3–CO–CH3 + CH3MgCl (X) → (CH3)3C–OMgCl HOH, H+
⟶
(CH3)3C–OH + Mg(OH)Cl

Teacher's Note:
1. Count carbons: acetone (3 C) + the alkyl of RMgX must give the 4-carbon tert-butyl alcohol, so R = CH3.

Question 30: Which of the following is the correct order of relative strength of acids?
(a) ClCH2COOH > BrCH2COOH > FCH2COOH
(b) BrCH2COOH > ClCH2COOH > FCH2COOH
(c) FCH2COOH > ClCH2COOH > BrCH2COOH
(d) ClCH2COOH > FCH2COOH > BrCH2COOH
Show Answer & Explanation

Answer: (c) FCH2COOH > ClCH2COOH > BrCH2COOH

Explanation:
1. The electron withdrawing strength of halogen groups is in the order of F > Cl > Br. Hence, the strength of acids is FCH2COOH > ClCH2COOH > BrCH2COOH.

Teacher's Note:
1. Acid strength of haloacids follows the electronegativity of the halogen: F > Cl > Br > I.

Assertion–Reason Questions

Question 31:
Assertion (A): Aromatic aldehydes and formaldehyde undergo Cannizzaro reaction.
Reason (R): Aromatic aldehydes are almost as reactive as formaldehyde.
(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: (c) A is true, but R is false.

Explanation:
1. Aromatic aldehydes and formaldehyde do not contain α-hydrogen and thus undergo Cannizzaro reaction. Formaldehyde is more reactive than aromatic aldehydes.

Teacher's Note:
1. The condition for Cannizzaro reaction is the absence of α-hydrogen, not high reactivity.

Question 32:
Assertion (A): α-Hydrogen atoms in aldehydes and ketones are acidic.
Reason (R): The anion left after the removal of α-hydrogen is stabilised by inductive effect.
(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: (c) A is true, but R is false.

Explanation:
1. The anion left after the removal of α-hydrogen is stabilized by resonance effect.

Teacher's Note:
1. The carbanion is delocalised onto the carbonyl oxygen (enolate ion); it is this resonance that makes α-H acidic.

Question 33:
Assertion (A): Hydrogen bonding in carboxylic acids is stronger than alcohols.
Reason (R): Highly branched carboxylic acids are more acidic than unbranched acids.
(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: (c) A is true, but R is false.

Explanation:
1. Highly branched carboxylic acids are less acidic than unbranched acids. The +I effect of alkyl groups in branched acid increases the magnitude of negative charge. Thus, –COOH group is shielded from solvent molecules and cannot be stabilized by solvation as effectively as in unbranched carboxylic acids.

Teacher's Note:
1. Alkyl groups are electron-releasing: more alkyl branching means a less stable carboxylate ion and a weaker acid.

Question 34:
Assertion (A): m-Chlorobenzoic acid is a stronger acid than p-chlorobenzoic acid.
Reason (R): In m-chlorobenzoic acid both –I-effect and +R-effect of Cl operate but in p-chlorobenzoic acid only +R-effect of Cl operates.
(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: (c) A is true, but R is false.

Explanation:
1. In p-chlorobenzoic acid, both +R and –I effect operate together but in m-chlorobenzoic acid only –I effect operates. Therefore, m-chlorobenzoic acid is a stronger acid than p-chlorobenzoic acid.

Teacher's Note:
1. Resonance (+R) effects act only at ortho and para positions; at the meta position only the inductive effect works.

Question 35:
Assertion (A): Ketones can be converted into acids by haloform reaction.
Reason (R): Addition of Grignard reagents to dry ice followed by hydrolysis gives ketones.
(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: (c) A is true, but R is false.

Explanation:
1. Addition of Grignard reagents to dry ice followed by hydrolysis gives carboxylic acid not ketone.
2. RMgX + O=C=O Dry
⟶
ether
R–CO–OMgX H+/H2O
⟶
R–CO–OH

Teacher's Note:
1. Grignard reagent + CO2 is a standard way to make an acid with one carbon more than the alkyl halide.

Question 36:
Assertion (A): Acetic acid in vapour state shows a molecular mass of 120.
Reason (R): It undergoes intermolecular hydrogen bonding.
(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. Acetic acid (molar mass 60) exists as a cyclic dimer held by two intermolecular hydrogen bonds even in the vapour state, so its observed molecular mass is 2 × 60 = 120.

Teacher's Note:
1. Carboxylic acid dimers survive in the vapour phase and in non-polar solvents like benzene, doubling the apparent molar mass.

Question 37:
Assertion (A): Nitration of benzoic acid gives m-nitrobenzoic acid.
Reason (R): Carboxyl group increases the electron density at the meta-position.
(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: (c) A is true, but R is false.

Explanation:
1. Carboxyl group only marginally decreases the electron density at m-position relative to o- and p-positions.

Teacher's Note:
1. –COOH deactivates the whole ring; the meta position is attacked only because it is the least deactivated.

Question 38:
Assertion (A): Boiling point of aldehydes lie in between parent alkanes and corresponding alcohols.
Reason (R): Aldehydes cannot form intermolecular hydrogen bonds like alcohols.
(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: (b) Both A and R are true, but R is not the correct explanation of A.

Explanation:
1. Aldehydes have higher molecular weight than parent alkanes as well as polarity in aldehydes shows higher boiling point than parent alkanes. Aldehydes do not have any hydrogen atom attached directly to the oxygen so they cannot form hydrogen bond with each other.

Teacher's Note:
1. Aldehydes boil above alkanes because of dipole–dipole attraction and below alcohols because they lack O–H hydrogen bonding.

Question 39:
Assertion (A): Carboxylic acids are stabilised by resonance.
Reason (R): Chloroacetic acid is weaker than acetic acid.
(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: (c) A is true, but R is false.

Explanation:
1. Chlorine atom has –I effect which increases the ionisation of chloroacetic acid and stabilizes the chloroacetate ion by dispersal of negative charge. In acetic acid, methyl group due to +I effect destabilizes the acetate ion by intensification of negative charge. Hence, chloroacetic acid dissociates to a greater extent than acetic acid.

Teacher's Note:
1. Any electron-withdrawing group on the α-carbon strengthens a carboxylic acid; electron-releasing groups weaken it.

Question 40:
Assertion (A): Benzaldehyde undergoes aldol condensation.
Reason (R): Aldehydes having α-hydrogen atom undergo aldol condensation.
(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. Aldehydes having a methyl or methylene group in the α-position or more correctly having atleast one hydrogen atom in the α-position undergo dimerisation in presence of a base at low temperature to form β-hydroxy aldehydes called aldols. As benzaldehyde does not have any α-hydrogen hence it does not undergoes aldol condensation.

Teacher's Note:
1. Benzaldehyde can take part in a cross aldol (as the acceptor), but it cannot undergo self aldol condensation.

Unit 8 Aldehydes Ketones and Carboxylic Acids Objective Questions & Solutions for Class 12 Chemistry

Class 12 Chemistry Unit 8 Aldehydes Ketones and Carboxylic Acids Objective Test Questions

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