JEE Chemistry Aldehydes Ketones and Carboxylic Acids MCQs Set 23

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 compounds gives a Grignard reagent?
(a) Formaldehyde
(b) Ethyl alcohol
(c) Methyl cyanide
(d) Methyl iodide
Show Answer & Explanation

Answer: (d) Methyl iodide

Explanation:
1. Only the alkyl halide can be converted to RMgX. The first three react with a Grignard reagent because they contain a carbonyl, an acidic OH or a cyano group.

Teacher's Note:
1. Grignard reagents give a secondary alcohol with aldehydes (primary with HCHO) and a tertiary alcohol with ketones.
2. Decide whether the product should be an aldehyde or a ketone from the type of alcohol or alkene given.

Question 2: In Rosenmund reduction, \( \ce{BaSO4} \) taken with the Pd catalyst acts as
(a) Promotor
(b) Catalytic poison
(c) Cooperator
(d) Absorber
Show Answer & Explanation

Answer: (b) Catalytic poison

Explanation:
1. BaSO4 reduces the activity of Pd so that the aldehyde is not reduced further, i.e. it acts as a catalyst poison.

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 3: Clemmensen reduction of acetone yields
(a) Ethanol
(b) Propane
(c) Ethanal
(d) Propanol
Show Answer & Explanation

Answer: (b) Propane

Explanation:
1. Zn-Hg/conc.
2. HCl reduces the >C=O group to >CH2, so acetone gives propane.

Teacher's Note:
1. Clemmensen (Zn-Hg/HCl, acid) and Wolff-Kishner (N2H4/KOH, base) both convert C=O to CH2; choose by the acid or base sensitivity of the rest of the molecule.
2. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.

Question 4: The catalyst \( \ce{SnCl2/HCl} \) is used in
(a) Stephen reduction
(b) Cannizzaro reaction
(c) Clemmensen reduction
(d) Rosenmund reduction
Show Answer & Explanation

Answer: (a) Stephen reduction

Explanation:
1. Stephen reduction converts a nitrile into an aldehyde using \( \ce{SnCl2} \) and HCl, followed by hydrolysis.

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 5: Methyl ethyl ketone is prepared by the oxidation of
(a) 2-Propanol
(b) 1-Butanol
(c) 2-Butanol
(d) t-Butyl alcohol
Show Answer & Explanation

Answer: (c) 2-Butanol

Explanation:
1. Butan-2-ol is a secondary alcohol, and its oxidation gives butanone (methyl ethyl ketone).

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 6: Benzaldehyde can be prepared by oxidation of toluene by
(a) Acidic \( \ce{KMnO4} \)
(b) \( \ce{K2Cr2O7} \)
(c) \( \ce{CrO2Cl2} \)
(d) All of these
Show Answer & Explanation

Answer: (c) \( \ce{CrO2Cl2} \)

Explanation:
1. Only chromyl chloride (Etard reaction) stops at the aldehyde stage.
2. Acidic KMnO4 and dichromate carry toluene on to benzoic acid.

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. List the standard preparations: oxidation of alcohols, ozonolysis, hydration of alkynes, Rosenmund, Stephen, Etard, Gattermann-Koch and Friedel-Crafts acylation.

Question 7: Which gas, passed into warm dilute \( \ce{H2SO4} \) containing \( \ce{HgSO4} \), gives acetaldehyde?
(a) \( \ce{CH4} \)
(b) \( \ce{C2H6} \)
(c) \( \ce{C2H4} \)
(d) \( \ce{C2H2} \)
Show Answer & Explanation

Answer: (d) \( \ce{C2H2} \)

Explanation:
1. Hydration of ethyne under these conditions forms vinyl alcohol, which tautomerises to acetaldehyde.

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 8: \( \ce{CH3COCH3} \) can be obtained by
(a) Heating acetaldehyde with methanol
(b) Oxidation of propyl alcohol
(c) Oxidation of isopropyl alcohol
(d) Reduction of propionic acid
Show Answer & Explanation

Answer: (c) Oxidation of isopropyl alcohol

Explanation:
1. Oxidising the secondary alcohol propan-2-ol gives acetone.
2. Propyl alcohol is primary and gives propanal or propanoic acid.

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 9: Propyne on hydrolysis in the presence of HCl and \( \ce{HgSO4} \) gives
(a) Acetaldehyde
(b) Acetone
(c) Formaldehyde
(d) None of these
Show Answer & Explanation

Answer: (b) Acetone

Explanation:
1. Markovnikov hydration of propyne gives the enol of acetone, which tautomerises to propanone.

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 10: Formaldehyde reacts with ammonia to give a urinary antiseptic compound. The reactant is
(a) \( \ce{HCHO} \)
(b) \( \ce{CH3CHO} \)
(c) \( \ce{C6H5CHO} \)
(d) \( \ce{C6H5CH2CHO} \)
Show Answer & Explanation

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

Explanation:
1. Six molecules of methanal with four of ammonia give hexamethylenetetramine (urotropine), used as a urinary antiseptic.

Teacher's Note:
1. Urotropine, (CH2)6N4, comes from methanal and ammonia; it is a urinary antiseptic.
2. Check each reagent for whether it stops at the carbonyl stage or goes on to the acid.

Question 11: Hydrolysis of the ozonide of but-1-ene gives
(a) Ethylene only
(b) Acetaldehyde and formaldehyde
(c) Propionaldehyde and formaldehyde
(d) Acetaldehyde only
Show Answer & Explanation

Answer: (c) Propionaldehyde and formaldehyde

Explanation:
1. \( \ce{CH3CH2CH=CH2} \) is cleaved at the double bond to give propanal, \( \ce{CH3CH2CHO} \), and methanal, \( \ce{HCHO} \).

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 12: Ketones are prepared by
(a) Clemmensen reduction
(b) Cannizzaro reaction
(c) Rosenmund reduction
(d) Oppenauer oxidation
Show Answer & Explanation

Answer: (d) Oppenauer oxidation

Explanation:
1. Oppenauer oxidation converts secondary alcohols to ketones with aluminium alkoxide and excess acetone.
2. The other reactions do not form ketones.

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 13: Ozone reacts with ethene to form an ozonide. On hydrolysis (reductive work-up) it forms
(a) Ethylene oxide
(b) \( \ce{HCHO} \)
(c) Ethylene glycol
(d) Ethyl alcohol
Show Answer & Explanation

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

Explanation:
1. Cleavage of \( \ce{CH2=CH2} \) at the double bond gives two molecules of methanal.

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 14: \( \ce{CH3CH2C#CH} \) with \( \ce{HgSO4} \)/\( \ce{H2SO4} \) gives A. The compound A is
(a) \( \ce{CH3CH2COCH3} \)
(b) \( \ce{CH3CH2CH2CHO} \)
(c) \( \ce{CH3CH2CH2COOH} \)
(d) None of these
Show Answer & Explanation

Answer: (a) \( \ce{CH3CH2COCH3} \)

Explanation:
1. Markovnikov hydration of the terminal alkyne puts the carbonyl on the second carbon, giving butan-2-one.

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 15: When a mixture of methane and oxygen is passed through heated molybdenum oxide, the main product is
(a) Methanoic acid
(b) Ethanal
(c) Methanol
(d) Methanal
Show Answer & Explanation

Answer: (d) Methanal

Explanation:
1. Controlled oxidation of methane over molybdenum oxide gives methanal.

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 16: Benzoin is
(a) A compound containing an aldehyde and a ketonic group
(b) An alpha,beta-unsaturated acid
(c) An alpha-hydroxy aldehyde
(d) An alpha-hydroxy ketone
Show Answer & Explanation

Answer: (d) An alpha-hydroxy ketone

Explanation:
1. Benzoin is \( \ce{C6H5CH(OH)COC6H5} \), an alpha-hydroxy ketone formed by benzoin condensation of benzaldehyde.

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: The oxidation of benzyl chloride with lead nitrate gives
(a) Benzyl alcohol
(b) Benzoic acid
(c) Benzaldehyde
(d) p-Chlorobenzaldehyde
Show Answer & Explanation

Answer: (c) Benzaldehyde

Explanation:
1. Benzyl chloride heated with aqueous lead nitrate (or copper nitrate) is oxidised to benzaldehyde.

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 18: The reaction \( \ce{R-CH=CH2 + CO + H2} \) (high temperature, high pressure) giving \( \ce{RCH2CH2CHO} \) is called
(a) Mendius reaction
(b) Oxo process
(c) Sandmeyer reaction
(d) Stephen reaction
Show Answer & Explanation

Answer: (b) Oxo process

Explanation:
1. Hydroformylation of an alkene with CO and H2 over a cobalt catalyst is the oxo process.

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: Glycerol reacts with potassium bisulphate to produce
(a) Allyl iodide
(b) Acryl aldehyde
(c) Allyl sulphate
(d) Glycerol trisulphate
Show Answer & Explanation

Answer: (b) Acryl aldehyde

Explanation:
1. KHSO4 dehydrates glycerol twice to acrolein, \( \ce{CH2=CH-CHO} \) (acryl aldehyde).

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: The reagent used in the Gattermann-Koch aldehyde synthesis is
(a) \( \ce{Pb/BaSO4} \)
(b) Alkaline \( \ce{KMnO4} \)
(c) Acidic \( \ce{KMnO4} \)
(d) \( \ce{CO + HCl} \)
Show Answer & Explanation

Answer: (d) \( \ce{CO + HCl} \)

Explanation:
1. Benzene is formylated by CO and HCl with anhydrous AlCl3 and CuCl.

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 21: An alkene of formula \( \ce{C9H18} \) on ozonolysis gives 2,2-dimethylpropanal and butan-2-one. The alkene is
(a) 2,2,4-Trimethylhex-3-ene
(b) 2,2,6-Trimethylhex-3-ene
(c) 2,3,4-Trimethylpent-2-ene
(d) 2,2,4-Trimethylhex-2-ene
Show Answer & Explanation

Answer: (a) 2,2,4-Trimethylhex-3-ene

Explanation:
1. Joining \( \ce{(CH3)3C-CH} \) and \( \ce{C(CH3)CH2CH3} \) through the double bond gives \( \ce{(CH3)3C-CH=C(CH3)CH2CH3} \), which is 2,2,4-trimethylhex-3-ene.

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 22: In \( \ce{CH3COCH3 + X} \) giving \( \ce{(CH3)3C-OMgCl} \), followed by hydrolysis giving Y + Mg(OH)Cl, the reactant X and product Y are
(a) X = \( \ce{MgCl2} \); Y = \( \ce{CH3CH=CH2} \)
(b) X = \( \ce{CH3MgCl} \); Y = \( \ce{C2H5COCH3} \)
(c) X = \( \ce{CH3MgCl} \); Y = \( \ce{(CH3)3C-OH} \)
(d) X = \( \ce{C2H5MgCl} \); Y = \( \ce{(CH3)3C-OH} \)
Show Answer & Explanation

Answer: (c) X = \( \ce{CH3MgCl} \); Y = \( \ce{(CH3)3C-OH} \)

Explanation:
1. Methylmagnesium chloride adds to the carbonyl of acetone to give the alkoxide \( \ce{(CH3)3C-OMgCl} \), and hydrolysis gives tert-butyl alcohol.

Teacher's Note:
1. Use the tests: Tollens' and Fehling's for aldehydes, iodoform for CH3CO- and CH3CH(OH)-, 2,4-DNP for any carbonyl.
2. Aldol needs alpha-hydrogen; Cannizzaro needs none.

Question 23: When m-chlorobenzaldehyde is treated with 50% KOH solution, the products are
(a) 1,2-Bis(3-hydroxyphenyl)ethane-1,2-diol
(b) m-Hydroxybenzoate and m-hydroxybenzyl alcohol
(c) m-Chlorobenzoate and m-chlorobenzyl alcohol
(d) 1,2-Bis(3-chlorophenyl)ethane-1,2-diol
Show Answer & Explanation

Answer: (c) m-Chlorobenzoate and m-chlorobenzyl alcohol

Explanation:
1. The aldehyde has no alpha-hydrogen, so it undergoes Cannizzaro reaction in strong alkali.
2. The aryl chlorine is not replaced.

Teacher's Note:
1. Cannizzaro reaction: an aldehyde with no alpha-hydrogen, in strong alkali, gives equal amounts of alcohol and carboxylate through hydride transfer.
2. Aldol needs alpha-hydrogen; Cannizzaro needs none.

Question 24: A and B in \( \ce{R-CO-R'} \) (HCN/KCN) giving A, then B giving \( \ce{RR'C(OH)CH2NH2} \) are
(a) A = \( \ce{RR'C(OH)CN} \), B = \( \ce{LiAlH4} \)
(b) A = \( \ce{RR'C(OH)COOH} \), B = \( \ce{NH3} \)
(c) A = \( \ce{RR'C(OH)CN} \), B = \( \ce{H3O^+} \)
(d) A = \( \ce{RR'C(OH)CH2CN} \), B = NaOH
Show Answer & Explanation

Answer: (a) A = \( \ce{RR'C(OH)CN} \), B = \( \ce{LiAlH4} \)

Explanation:
1. HCN adds to the carbonyl to give the cyanohydrin A. Reducing the cyano group with LiAlH4 gives the amino alcohol.

Teacher's Note:
1. Compare reactivity with steric hindrance and electron donation: HCHO > RCHO > ArCHO > R2CO > Ar2CO.
2. Use the tests: Tollens' and Fehling's for aldehydes, iodoform for CH3CO- and CH3CH(OH)-, 2,4-DNP for any carbonyl.

Question 25: Reduction of aldehydes and ketones to hydrocarbons takes place in the presence of
(a) Zinc amalgam and HCl
(b) \( \ce{Pd/BaSO4} \)
(c) Anhydrous \( \ce{AlCl3} \)
(d) Ni/Pt
Show Answer & Explanation

Answer: (a) Zinc amalgam and HCl

Explanation:
1. Zn-Hg with concentrated HCl (Clemmensen reduction) reduces >C=O to >CH2.

Teacher's Note:
1. Clemmensen (Zn-Hg/HCl, acid) and Wolff-Kishner (N2H4/KOH, base) both convert C=O to CH2; choose by the acid or base sensitivity of the rest of the molecule.
2. Use the tests: Tollens' and Fehling's for aldehydes, iodoform for CH3CO- and CH3CH(OH)-, 2,4-DNP for any carbonyl.

Question 26: Reduction of >C=O to \( \ce{CH2} \) can be carried out with
(a) Catalytic reduction
(b) \( \ce{Na/C2H5OH} \)
(c) Wolff-Kishner reduction
(d) \( \ce{LiAlH4} \)
Show Answer & Explanation

Answer: (c) Wolff-Kishner reduction

Explanation:
1. Catalytic reduction, Na/alcohol and LiAlH4 give alcohols.
2. Hydrazine with KOH (Wolff-Kishner) converts the carbonyl to a methylene group.

Teacher's Note:
1. Clemmensen (Zn-Hg/HCl, acid) and Wolff-Kishner (N2H4/KOH, base) both convert C=O to CH2; choose by the acid or base sensitivity of the rest of the molecule.
2. Aldol needs alpha-hydrogen; Cannizzaro needs none.

Question 27: For \( \ce{C6H5CHO} \) which of the following is incorrect?
(a) On oxidation it yields benzoic acid
(b) It is used in perfumery
(c) It is an aromatic aldehyde
(d) On reduction it yields phenol
Show Answer & Explanation

Answer: (d) On reduction it yields phenol

Explanation:
1. Reduction of benzaldehyde gives benzyl alcohol or toluene, never phenol.

Teacher's Note:
1. Compare reactivity with steric hindrance and electron donation: HCHO > RCHO > ArCHO > R2CO > Ar2CO.
2. Use the tests: Tollens' and Fehling's for aldehydes, iodoform for CH3CO- and CH3CH(OH)-, 2,4-DNP for any carbonyl.

Question 28: Which of the following is incorrect?
(a) \( \ce{FeCl3} \) 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) \( \ce{NaHSO3} \) 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 detects aldehydes (a reducing group); unsaturation is detected with Baeyer's reagent or bromine water.

Teacher's Note:
1. Tollens' reagent, [Ag(NH3)2]+, is reduced to silver by aldehydes and not by ketones.
2. Aldol needs alpha-hydrogen; Cannizzaro needs none.

Question 29: Acetophenone can be prepared by (1) oxidation of 1-phenylethanol, (2) reaction of benzaldehyde with methylmagnesium bromide, (3) Friedel-Crafts reaction of benzene with acetyl chloride, (4) distillation of calcium benzoate. Correct choice:
(a) 1 and 2
(b) 1 and 4
(c) 1 and 3
(d) 3 and 4
Show Answer & Explanation

Answer: (c) 1 and 3

Explanation:
1. Oxidation of the secondary alcohol and Friedel-Crafts acylation both give acetophenone.
2. Benzaldehyde with CH3MgBr gives 1-phenylethanol, and calcium benzoate gives benzophenone.

Teacher's Note:
1. Compare reactivity with steric hindrance and electron donation: HCHO > RCHO > ArCHO > R2CO > Ar2CO.
2. Use the tests: Tollens' and Fehling's for aldehydes, iodoform for CH3CO- and CH3CH(OH)-, 2,4-DNP for any carbonyl.

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