Aldehydes,ketones and carboxylic acids
SOME DISTINGUISHING TESTS:
MULTIPLE CHOICE QUESTIONS (1 MARKS)
1.) Which aldehyde will give Cannizzaro’s reaction?
(a) CH3CH2CH2CHO (b) CH3CH2CHCHO (c) (CH3)3CCHO (d) (CH3)2CH2CH2CHO
2.) Carboxylic acids are more acidic than phenol and alcohol because of
(a) Formation of dimers (b) Resonance stabilization of their conjugate base (c) Highly acidic
hydrogen (d) Intermolecular hydrogen bonding
3.) Aldehydes and ketones undergo __________ reactions.
a) electrophilic addition b) electrophilic substitution c) nucleophilic addition d) nucleophilic
substitution
4.) What is the correct order of reactivity of the following towards nucleophilic addition?
a) Methanal > Ethanal > Acetone b) Acetone > Ethanal > Methanal c) Methanal > Acetone >
Ethanal d) Ethanal > Methanal > Acetone
5.) Identify the reagent for the conversion of but-2-ene to ethanal.
a) O3/H2O-Zn dust b) H2O, H2SO4, HgSO4 c) PCC d) DIBAL-H
6.) Which of the reactions below can result in ketones?
a) Oxidation of primary alcohols b) Oxidation of secondary alcohols c) Dehydrogenation of
tertiary alcohols d) Dehydrogenation of primary alcohols
7.) Which of the following orders of relative strengths of acids is correct?
(a) ClCH2COOH > FCH2COOH > BrCH2COOH (b) ClCH2COOH > BrCH2COOH > FCH2COOH (c)
BrCH2COOH > ClCH2COOH > FCH2COOH (d) FCH2COOH > ClCH2COOH > BrCH2COOH
8.) The reagent which does not react with both Propanone and Benzaldehyde:
(a) Grignard reagent (b) Tollen’s reagent (c) Zn-Hg amalgam (d)Fehling solution
9.) Which of the following compound will not give NaHCO3 test?
(a)Carbolic acid (b)Formic acid (c) Acetic acid (d) Benzoic acid
10.) In Clemmensen Reduction carbonyl compound is treated with __
(a) Zinc amalgam + HCl (b) Sodium amalgam + HCl (c) Zinc amalgam + nitric acid (d) Sodium
amalgam + HNO3
ASSERTION REASON TYPE QUESTIONS(1MARKS)
Note : In the following questions a statement of assertion followed by a statement of reason is
given. Choose the correct answer out of the following choices.
a) Assertion and reason both are correct statements and reason is correct explanation for
assertion.
b) Assertion and reason both are correct statements but reason is not correct explanation for
assertion.
c) Assertion is correct statement but reason is wrong statement.
d) Assertion is wrong statement but reason is correct statement.
11.) Assertion: Methanal, ethanal and propanone are miscible with water in all proportions.
Reason: The lower members of aldehydes and ketones form hydrogen bond with water.
12.) Assertion: Aldehydes are generally more reactive than ketones in nucleophilic addition
reactions.
Reason: Sterically, the presence of two relatively large substituents in ketones hinder the
approach of nucleophile to carbonyl carbon than in aldehydes having only one such substituent.
13.) Assertion: Sodium hydrogen sulphite adds to aldehydes and ketones to form the addition
product.
Reason: Reaction of aldehydes with Sodium hydrogen sulphite is useful for separation and
purification of aldehydes.
14.) Assertion: Pka of acetic acid is lower than that of phenol
Reason: Phenoxide ion is more resonance stabilized than acetate ion.
15.) Assertion : α-hydrogen atoms of carbonyl compounds are acidic in nature.
Reason: The strong electron donating effect of the carbonyl group and resonance destabilisation
of the conjugate base makes the alpha hydrogen acidic.
16) Write the structure of 3-oxopentanal.
17) Give a chemical test to distinguish between Benzoic acid and Phenol
18) Formaldehyde does not undergo aldol condensation reaction. Why?
19) Aldehydes and Ketones have lower boiling points than corresponding alcohols. Why?
20) Arrange the following compounds in increasing order of their reactivity in nucleophilic
addition reactions: (i)Ethanal, Propanal, Propanone, Butanone. (ii)Benzaldehyde,
p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
21) Write the structure of the product formed in the following reaction
22) Carboxylic acids do not give characteristic reactions of carbonyl group. Why?
23) Write the reagents required in the following reactions.
24) Why does benzoic acid not undergo Friedel-Craft reaction?
25) Why Pka of F-CH2COOH is lower than that of Cl–CH2COOH?
26) Draw structures of the following derivatives: (i) The 2,4-dinitrophenylhydrazone of
benzaldehyde (ii) Cyclopropanone oxime
27) How will you convert (i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde
28) Give the structure of the following compounds. (i) 4-Nitropropiophenone (ii)
2-Hydroxycyclopentanecarbaldehyde
29) Explain each of the following. (i) Cyanohydrin (ii) Acetal
30) What happens when Formaldehyde is treated with conc.KOH?
31. Give plausible explanation for each of the following:
(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not.
(ii) There are two – NH2 groups in semicarbazide. However, only one is involved in the
formation of semicarbazones.
(iii)During the preparation of esters from a carboxylic acid and an alcohol in the presence of an
acid catalyst, the water or the ester should be removed as soon as it is formed
32. Identify the compounds A, B and C in the following reaction.
33. Give simple chemical tests to distinguish between the following pairs of compounds. (i)
Propanal and Propanone (ii) Acetophenone and Benzophenone (iii)Phenol and Benzoic acid
34. Write structures of compounds A, B and C in the following reactions:
35. Predict the products of the following reactions.
Long Answer Type Questions (5 marks each):
36. Describe the following : (i) Aldol Condensation (ii)Cannizzaro Reaction (iii)Clemmensen
Reduction (iv)Rosenmund Reduction (v) Hell Volhard Zelinsky Reaction.
.
37. An aromatic compound ‘A’ (Molecular formula C8H8O) gives positive 2,4-DNP test. It gives a
yellow precipitate of compound ‘B’ on treatment with iodine and sodium hydroxide solution.
Compound ‘A’ does not give Tollen’s or Fehling’s test. On drastic oxidation with potassium
permanganate, it forms a carboxylic acid ‘C’ (Molecular formula C7H6O2 ), which is also formed
along with the yellow compound in the above reaction. Identify A, B and C and write all the
reactions involved.
Case based; Source based Integrated Questions 38.) Read the following passage and answer the
questions given below the passage. Reductive alkylation is the term applied to the process of
introducing alkyl groups into ammonia or a primary or secondary amine by means of an
aldehyde or ketone in the presence of a reducing agent. The present discussion is limited to
those reductive alkylations in which the reducing agent is hydrogen and a catalyst or "nascent"
hydrogen, usually from a metal acid combination; most of these reductive alkylations have been
carried out with hydrogen and a catalyst. The principal variation excluded is that in which the
reducing agent is formic acid or one of its derivatives; this modification is known as the Leuckart
reaction. The process of reductive alkylation of ammonia consists in the addition of ammonia to
a carbonyl compound and reduction of the addition compound or its dehydration product. The
reaction usually is carried out in ethanol solution when the reduction is to be affected
catalytically Since the primary amine is formed in the presence of the aldehyde it may react in
the same way as ammonia, yielding an addition compound, a Schiff's base (RCH= NCH2R) and
finally, a secondary amine. Similarly, the primary amine may react with the imine, forming an
addition product which also is reduced to a secondary amine Finally, the secondary amine may
react with either the aldehyde or the imine to give products which are reduced to tertiary
amines. Similar reactions may occur when the carbonyl compound employed is a ketone
A] Write equations for the following reactions.
(i) Acetone with hydroxyl amine (ii) Ethanal with ammonia
B] A compound gives 2,4 DNP test, further it reduces Tollen’s reagent. what conclusions can be
drawn from this information?
C]What type of reaction takes place when aldehydes or ketones are treated with ammonia and
its derivatives?
39.) Read the following passage and answer the questions given below the passage. The
addition reaction of enol or enolate to the carbonyl functional group of aldehyde or ketone is
known as aldol addition. The b-hydroxy aldehyde or b-hydroxyketone so obtained undergo
dehydration in second step to produce a conjugated enone. The first part of reaction is an
addition reaction and the second part is an elimination reaction. Carbonyl compound having
alpha-hydrogen undergoes aldol condensation reaction. When an aldehyde with no
alpha-hydrogen reacts with concentrated aqueous NaOH, half the aldehyde is converted to
carboxylic acid salt and other half is converted to an alcohol. In other words, half of the reactant
is oxidized and another half is reduced. This reaction is known as Cannizzaro reaction.
A] How will you convert ethanol to But-2-enal?
B] Name the products of aldol condensation of Propanone and Ethanal.
C] What happens when Benzaldehyde is treated with Conc. NaOH?
40.) Read the following passage and answer the questions given below the passage. The
carbonyl group of aldehydes and ketones is reduced to -CH2- group on treatment with zinc
amalgam and concentrated hydrochloric acid [Clemmensen reduction] or with hydrazine
followed by heating with sodium or potassium hydroxide in high boiling solvent such as
ethylene glycol (Wolf-Kishner reduction). Aldehydes differ from ketones in their oxidation
reactions. Aldehydes are easily oxidised to carboxylic acids on treatment with common oxidising
agents like nitric acid, potassium permanganate, potassium dichromate, etc. Even mild oxidising
agents, mainly Tollens’ reagent and Fehling’s reagent also oxidise aldehydes. Ketones are
generally oxidised under vigorous conditions, i.e., strong oxidising agents and at elevated
temperatures. Their oxidation involves carboncarbon bond cleavage to afford a mixture of
carboxylic acids having lesser number of carbon atoms than the parent ketone. A] Write a
chemical equation to convert Propanone to propane. Mention the name of the reaction.
B]Name the reagents used in the following conversions? i) Butan-1-ol to Butanal ii) Ethanal to
Ethanoic acid
