JEE Chemistry Aldehydes Ketones and Carboxylic Acids MCQs Set 22

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Chapter-wise Objective Questions: Aldehydes Ketones and Carboxylic Acids

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Multiple Choice Questions

Question 1: In aldehydes and ketones, the carbon of the carbonyl group is
(a) \( \ce{sp^3} \) hybridised
(b) \( \ce{sp^2} \) hybridised
(c) \( \ce{sp} \) hybridised
(d) Unhybridised
Show Answer & Explanation

Answer: (b) \( \ce{sp^2} \) hybridised

Explanation:
1. The carbonyl carbon forms three sigma bonds (two to substituents, one to O) and one pi bond, so it is sp2 hybridised and trigonal planar.

Teacher's Note:
1. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.
2. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.

Question 2: The IUPAC name of \( \ce{(CH3)2CH-CO-CH2CH2OH} \) is
(a) 1-Hydroxy-4-methylpentan-3-one
(b) 2-Methyl-5-hydroxypentan-3-one
(c) 4-Methyl-3-oxopentan-1-ol
(d) Hexanol-1-one-3
Show Answer & Explanation

Answer: (a) 1-Hydroxy-4-methylpentan-3-one

Explanation:
1. The longest chain has five carbons: HOCH2-CH2-CO-CH(CH3)-CH3.
2. Number from the OH end so the ketone is C3: 1-hydroxy-4-methylpentan-3-one.

Teacher's Note:
1. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.
2. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.

Question 3: Glyoxal is
(a) \( \ce{CH2-CH2O} \) (cyclic oxide)
(b) Ethane-1,2-diol
(c) \( \ce{OHC-CHO} \)
(d) Hydroxyethanal
Show Answer & Explanation

Answer: (c) \( \ce{OHC-CHO} \)

Explanation:
1. Glyoxal is ethanedial, \( \ce{OHC-CHO} \), the simplest dialdehyde.

Teacher's Note:
1. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.
2. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.

Question 4: Aldehydes are isomeric with
(a) Ketones
(b) Ethers
(c) Alcohols
(d) Fatty acids
Show Answer & Explanation

Answer: (a) Ketones

Explanation:
1. An aldehyde RCHO and a ketone with the same number of carbons share the formula, for example propanal and propanone, \( \ce{C3H6O} \).

Teacher's Note:
1. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.
2. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.

Question 5: Which of the following compounds does not contain an -OH group?
(a) Phenol
(b) Carboxylic acid
(c) Aldehydes
(d) Alcohols
Show Answer & Explanation

Answer: (c) Aldehydes

Explanation:
1. Aldehydes contain the -CHO group and have no hydroxyl group.

Teacher's Note:
1. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.
2. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.

Question 6: The IUPAC name of \( \ce{CH3COCH3} \) is
(a) Acetone
(b) Propanone
(c) Dimethyl ketone
(d) Propanal
Show Answer & Explanation

Answer: (b) Propanone

Explanation:
1. Three carbons with the carbonyl on the middle one give propanone.

Teacher's Note:
1. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.
2. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.

Question 7: The compound in which two valencies of the carbonyl carbon are satisfied by two alkyl groups is called
(a) Aldehyde
(b) Ketone
(c) Acid
(d) Acid chloride
Show Answer & Explanation

Answer: (b) Ketone

Explanation:
1. R-CO-R' with two alkyl groups on the carbonyl carbon is a ketone.

Teacher's Note:
1. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.
2. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.

Question 8: Ethanedial contains the functional group(s)
(a) One ketonic
(b) Two aldehydic
(c) One double bond
(d) Two double bonds
Show Answer & Explanation

Answer: (b) Two aldehydic

Explanation:
1. Ethanedial is \( \ce{OHC-CHO} \) and carries two -CHO groups.

Teacher's Note:
1. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.
2. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.

Question 9: In the group >C=O the carbonyl carbon is joined to other atoms by
(a) Two sigma and one pi bonds
(b) Three sigma and one pi bonds
(c) One sigma and two pi bonds
(d) Two sigma and two pi bonds
Show Answer & Explanation

Answer: (b) Three sigma and one pi bonds

Explanation:
1. The carbonyl carbon has one sigma and one pi bond to oxygen plus two sigma bonds to R and R', i.e. three sigma and one pi.

Teacher's Note:
1. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.
2. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.

Question 10: Which type of isomerism is shown by pentanone?
(a) Chain isomerism
(b) Position isomerism
(c) Functional isomerism
(d) All of these
Show Answer & Explanation

Answer: (d) All of these

Explanation:
1. Pentanone shows position isomerism (pentan-2-one and pentan-3-one), chain isomerism (3-methylbutanone) and functional isomerism (pentanal).

Teacher's Note:
1. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.
2. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.

Question 11: The IUPAC name of \( \ce{CCl3CHO} \) is
(a) Chloral
(b) Trichloroacetaldehyde
(c) 1,1,1-Trichloroethanal
(d) 2,2,2-Trichloroethanal
Show Answer & Explanation

Answer: (d) 2,2,2-Trichloroethanal

Explanation:
1. The CHO carbon is C1 and the three chlorines are on C2, so the name is 2,2,2-trichloroethanal.

Teacher's Note:
1. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.
2. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.

Question 12: Which of the following is a mixed ketone?
(a) Pentanone
(b) Acetophenone
(c) Benzophenone
(d) Butanone
Show Answer & Explanation

Answer: (b) Acetophenone

Explanation:
1. A mixed ketone has two different groups on the carbonyl, here methyl and phenyl in acetophenone.

Teacher's Note:
1. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.
2. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.

Question 13: Chloral is
(a) \( \ce{CCl3CHO} \)
(b) \( \ce{CCl3COCH3} \)
(c) \( \ce{CCl3COCCl3} \)
(d) \( \ce{CCl3CH2OH} \)
Show Answer & Explanation

Answer: (a) \( \ce{CCl3CHO} \)

Explanation:
1. Chloral is trichloroethanal, \( \ce{CCl3CHO} \).

Teacher's Note:
1. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.
2. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.

Question 14: Carbonyl compounds are usually
(a) Ethers, aldehydes, ketones and carboxylic acids
(b) Aldehydes, ketones and carboxylic acids
(c) Aldehydes and ketones
(d) Carboxylic acids
Show Answer & Explanation

Answer: (c) Aldehydes and ketones

Explanation:
1. The name carbonyl compounds is used for aldehydes and ketones.

Teacher's Note:
1. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.
2. Remember common names: formaldehyde, acetaldehyde, chloral, glyoxal, acetone, acetophenone, benzophenone.

Question 15: Which of the following aldehydes is most reactive towards nucleophiles?
(a) \( \ce{C6H5CHO} \)
(b) \( \ce{CH3CHO} \)
(c) \( \ce{HCHO} \)
(d) All are equally reactive
Show Answer & Explanation

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

Explanation:
1. Formaldehyde has two hydrogens and no electron-donating group, so its carbonyl carbon is the most electrophilic and least hindered.

Teacher's Note:
1. The carbonyl carbon is sp2 with one pi bond, which is why nucleophilic addition is the typical reaction.
2. Name carbonyl compounds by choosing the longest chain that contains the C=O; aldehydes end in -al, ketones in -one.

Question 16: The end product in the sequence \( \ce{HC#CH} \) (1% HgSO4, 20% H2SO4) A, then CH3MgBr to B, then [O], is
(a) Acetic acid
(b) Isopropyl alcohol
(c) Acetone
(d) Ethanol
Show Answer & Explanation

Answer: (c) Acetone

Explanation:
1. Ethyne is hydrated to acetaldehyde (A)
2. Acetaldehyde with \( \ce{CH3MgBr} \) gives propan-2-ol (B) after hydrolysis, and oxidation of this secondary alcohol gives acetone.

Teacher's Note:
1. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 17: In the reaction RCOCl with \( \ce{H2} \) over Pd/BaSO4, the product P is
(a) \( \ce{RCH2OH} \)
(b) \( \ce{RCOOH} \)
(c) \( \ce{RCHO} \)
(d) \( \ce{RCH3} \)
Show Answer & Explanation

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

Explanation:
1. This is Rosenmund reduction: the poisoned catalyst stops reduction at the aldehyde stage.

Teacher's Note:
1. Aldehyde syntheses: Rosenmund (acid chloride, H2, Pd/BaSO4), Stephen (nitrile, SnCl2/HCl), Etard (toluene, CrO2Cl2), Gattermann-Koch (benzene, CO/HCl, AlCl3).
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 18: Acetophenone is prepared from
(a) Rosenmund reaction
(b) Sandmeyer reaction
(c) Wurtz reaction
(d) Friedel-Crafts reaction
Show Answer & Explanation

Answer: (d) Friedel-Crafts reaction

Explanation:
1. Benzene with acetyl chloride and anhydrous AlCl3 gives acetophenone by Friedel-Crafts acylation.

Teacher's Note:
1. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.
2. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.

Question 19: The compound which gives acetone on ozonolysis is
(a) \( \ce{CH3CH=CHCH3} \)
(b) \( \ce{(CH3)2C=C(CH3)2} \)
(c) \( \ce{C6H5CH=CH2} \)
(d) \( \ce{CH3CH=CH2} \)
Show Answer & Explanation

Answer: (b) \( \ce{(CH3)2C=C(CH3)2} \)

Explanation:
1. Each carbon of the double bond in tetramethylethene carries two methyl groups, so cleavage gives two molecules of acetone.
2. The others give aldehydes.

Teacher's Note:
1. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 20: Which of the following is prepared in the laboratory from benzene by a substitution reaction?
(a) Glyoxal
(b) Cyclohexane
(c) Acetophenone
(d) Hexabromocyclohexane
Show Answer & Explanation

Answer: (c) Acetophenone

Explanation:
1. Friedel-Crafts acylation of benzene is a substitution giving acetophenone.
2. Cyclohexane and hexabromocyclohexane need addition reactions.

Teacher's Note:
1. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.
2. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.

Question 21: Ketones R-CO-R1 (R = R1 = alkyl) can be obtained in one step by
(a) Hydrolysis of esters
(b) Oxidation of primary alcohols
(c) Oxidation of secondary alcohols
(d) Reaction of acid halide with alcohols
Show Answer & Explanation

Answer: (c) Oxidation of secondary alcohols

Explanation:
1. A secondary alcohol is oxidised directly to a ketone.
2. Primary alcohols give aldehydes or acids, and the other two give acids or esters.

Teacher's Note:
1. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.
2. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.

Question 22: The reaction \( \ce{CH3COCl} \) + 2[H] over Pd/BaSO4 giving \( \ce{CH3CHO + HCl} \) is called
(a) Reimer-Tiemann reaction
(b) Cannizzaro reaction
(c) Rosenmund reaction
(d) Reformatsky reaction
Show Answer & Explanation

Answer: (c) Rosenmund reaction

Explanation:
1. Reduction of an acid chloride to an aldehyde with poisoned palladium is the Rosenmund reduction.

Teacher's Note:
1. Aldehyde syntheses: Rosenmund (acid chloride, H2, Pd/BaSO4), Stephen (nitrile, SnCl2/HCl), Etard (toluene, CrO2Cl2), Gattermann-Koch (benzene, CO/HCl, AlCl3).
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 23: The oxidation of toluene to benzaldehyde by chromyl chloride is called
(a) Cannizzaro reaction
(b) Wurtz reaction
(c) Etard reaction
(d) Reimer-Tiemann reaction
Show Answer & Explanation

Answer: (c) Etard reaction

Explanation:
1. Chromyl chloride, \( \ce{CrO2Cl2} \), converts the methyl group of toluene to an aldehyde in the Etard reaction.

Teacher's Note:
1. Aldehyde syntheses: Rosenmund (acid chloride, H2, Pd/BaSO4), Stephen (nitrile, SnCl2/HCl), Etard (toluene, CrO2Cl2), Gattermann-Koch (benzene, CO/HCl, AlCl3).
2. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.

Question 24: Tertiary butyl alcohol is obtained from the action of methylmagnesium iodide on
(a) \( \ce{HCHO} \)
(b) \( \ce{CH3CHO} \)
(c) \( \ce{CH3COCH3} \)
(d) \( \ce{CO2} \)
Show Answer & Explanation

Answer: (c) \( \ce{CH3COCH3} \)

Explanation:
1. A ketone with a Grignard reagent gives a tertiary alcohol.
2. \( \ce{CH3MgI} \) adds to acetone to give \( \ce{(CH3)3COH} \).

Teacher's Note:
1. Grignard reagents give a secondary alcohol with aldehydes (primary with HCHO) and a tertiary alcohol with ketones.
2. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.

Question 25: The catalyst used in Rosenmund reduction is
(a) Pd/BaSO4
(b) Zn-Hg couple
(c) \( \ce{LiAlH4} \)
(d) \( \ce{Ni/H2} \)
Show Answer & Explanation

Answer: (a) Pd/BaSO4

Explanation:
1. Rosenmund reduction uses palladium on barium sulphate, partially poisoned.

Teacher's Note:
1. Aldehyde syntheses: Rosenmund (acid chloride, H2, Pd/BaSO4), Stephen (nitrile, SnCl2/HCl), Etard (toluene, CrO2Cl2), Gattermann-Koch (benzene, CO/HCl, AlCl3).
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 26: \( \ce{CH3CH2C#CH} \) on hydration with reagent R gives butanone. R is
(a) \( Hg^{2+} \)
(b) \( \ce{KMnO4} \)
(c) \( \ce{KClO3} \)
(d) \( \ce{K2Cr2O7} \)
Show Answer & Explanation

Answer: (a) \( Hg^{2+} \)

Explanation:
1. Hydration of a terminal alkyne with Hg2+ and dilute H2SO4 follows Markovnikov addition, giving the methyl ketone butanone.

Teacher's Note:
1. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.
2. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.

Question 27: Dry heating of calcium acetate gives
(a) Acetaldehyde
(b) Ethane
(c) Acetic acid
(d) Acetone
Show Answer & Explanation

Answer: (d) Acetone

Explanation:
1. \( \ce{(CH3COO)2Ca} \) on heating gives acetone and calcium carbonate.

Teacher's Note:
1. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 28: Acetophenone is prepared by the reaction of which pair in the presence of \( \ce{AlCl3} \) catalyst?
(a) Phenol and acetic acid
(b) Benzene and acetone
(c) Benzene and acetyl chloride
(d) Phenol and acetone
Show Answer & Explanation

Answer: (c) Benzene and acetyl chloride

Explanation:
1. Friedel-Crafts acylation uses benzene and an acyl chloride with AlCl3.

Teacher's Note:
1. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.
2. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.

Question 29: On heating calcium acetate and calcium formate, the product formed is
(a) \( \ce{CH3COCH3} \)
(b) \( \ce{CH3CHO} \)
(c) \( \ce{HCHO + CaCO3} \)
(d) \( \ce{CH3CHO + CaCO3} \)
Show Answer & Explanation

Answer: (d) \( \ce{CH3CHO + CaCO3} \)

Explanation:
1. A mixed calcium salt of formic and acetic acids gives acetaldehyde and calcium carbonate on dry heating.

Teacher's Note:
1. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

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