Hsslive-12. Aldehydes, Ketones & Carboxylic Acids
Hsslive-12. Aldehydes, Ketones & Carboxylic Acids
Hsslive-12. Aldehydes, Ketones & Carboxylic Acids
in ®
Previous HSE questions and Answers for the chapter “Aldehydes, Ketones and Carboxylic Acids”
Aldehydes, Ketones and Carboxylic Acids – Prepared by Anil Kumar K L, GHSS Ashtamudi Page 1
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ii) Aldehydes and ketones can be subjected to Clemmensen reduction and Wolff-Kishner reduction. Name the
reagents in both cases. (1)
b) How will you make the following conversions:
i) Ethanoic acid to ethanol.
ii) Propanoic acid to 2-chloropropanoic acid
iii) Toluene to benzoic acid. (3) [March 2010]
Ans: (a) i) Tollen’s test or Fehling’s test
ii) Clemmensen reduction: Zinc amalgam and Conc. HCl
Wolff-Kishner reduction: Hydrazine & KOH in ethylene glycol.
(b) i) By reduction using LiAlH4 followed by acidification, ethanoic acid gets converted to ethanol.
COOH
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iii) 3,4 –dinitrobenzoic acid is treated with LiAlH4 followed by reduction with H2 in presence of Pd, we
get 3,4-diaminobenzyl alcohol.
COOH CH2OH CH2OH
LiAlH4 H2/Pd
NO2
NO2 NO2 NH2
NO2 NO2 NH2
6. Aldehydes resemble ketones in many respects.
a) Give the reason for their resemblance. (1)
b) Give a reaction in which aldehydes resemble ketones. (1)
c) Write two tests to distinguish between aldehydes and ketones. (2)
d) What is Cannizzaro reaction? (1) [SAY 2011]
Ans: a) Because of the presence of carbonyl group in both aldehyde and ketones.
b) Both aldehydes and ketones undergo nucleophilic addition reaction with HCN and form cyanohydrins.
c) Aldehydes form bright silver mirror when heated with Tollens’ reagent (Tollens’ test).
When heated with Fehling’s solutions, aldehydes form red ppt (Fehling’s test). These two tests are not
answered by ketones.
d) Aldehydes having no α-hydrogen atom, when treated with conc. KOH undergo self oxidation and
reduction (disproportionation) to form alcohol and carboxylic acid salt. This reaction is called Cannizzaro
reaction.
2 HCHO Conc. KOH CH3-OH + H-COOK
Formaldehyde methanol potassium formate
7. a) Which named reaction is used to reduce CH3-CO-Cl to CH3-CHO? (1)
b) Aldehydes and ketones undergo reactions due to the presence of α-hydrogen atom.
i) Write the name reaction of aldehyde which takes place only because of the presence of α-hydrogen atom. (1)
ii) How will you bring about the above reaction? (1)
c) i) CH2Cl-COOH is a strong acid than CH3COOH. Why?
ii) How will you convert CH3-COOH to CH2Cl-COOH? (2) [March 2012]
Ans: (a) Rosenmund’s reduction
b) i) Aldol condensation
ii) By treating with dilute alkali (NaOH or KOH).
c) i) Due to the electron withdrawing inductive effect (-I effect) of Chlorine atom.
ii) By treating with Cl2 in presence of red phosphorus (HVZ reaction).
8. a) Complete the following: Write down the structures of A, B and C.
i) CH3-CH2-CHO KMnO4 A
ii) CH3-CH2-CO-CH3 Zn amalgam/HCl B
iii) CH3-CH2-CH2-COOH Bromine/Red P C
H2O
b) Write down the IUPAC names of A, B and C. (1½)
c) Explain the following reactions. i) Cannizzaro reaction. ii) Esterification. (1) [SAY 2012]
Ans: (a)
i) CH3-CH2-CHO KMnO4 CH3-CH2-COOH
ii) CH3-CH2-CO-CH3 Zn amalgam/HCl CH3-CH2-CH2-CH3
iii) CH3-CH2-CH2-COOH Bromine/Red P CH3-CH2-CHBr-COOH
H2O
(b) IUPAC name of A is propanoic acid, B is butane and C is 2-Bromobutanoic acid.
(c) i) Cannizzaro reaction: Aldehydes having no α-hydrogen atom, when treated with conc. KOH undergo self
oxidation and reduction (disproportionation) to form alcohol and carboxylic acid salt.
2 HCHO Conc. KOH CH3-OH + H-COOK
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ii) Esterification: Carboxylic acids when heated with alcohols or phenols in the presence of conc. H2SO4
or HCl gas, we get esters.
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Ans: (a) (i) Aldehydes having at least one α-hydrogen atom when heated with dilute alkali, we get α,β-
unsaturated aldehyde. This reaction is called Aldol condensation.
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CH3
C=O Zn/Hg
CH3 HCl
CO/HCl
An. AlCl3/Cu (2) [March 2015]
Ans: (a) Ethyl acetate or ethyl ethanoate [CH3-COOC2H5]
(b) (i) Tollens’ test and Fehling’s test
(ii) (1) Propane [CH3-CH2-CH3]
Benzaldehyde [C6H5-CHO]
(2) Clemmensen reduction and Gattermann-Koch Reaction
14. a) Explain aldol condensation taking CH3-CHO as example. (2)
b) Write the named reactions involved in the following conversions:
i) CH3-CO-Cl H2/Pd-BaSO4 CH3-CHO
ii) 2 HCHO NaOH HCOONa + CH3-OH (1)
c) How are the following conversions achieved?
i) CH3-CN CH3-COOH
ii) CH3-COOH CH2Cl-COOH (2) [SAY 2015]
Ans: (a) Refer the answer of Question no. 11 (a)
(b) i) Rosenmund’s reduction
ii) Cannizzaro’s reaction
(c) i) CH3-CN H2O/H+ CH3-COOH
ii) CH3-COOH Cl2/Red P CH2Cl-COOH
15. Aldehydes, Ketones and Carboxylic acids are Carbonyl compounds.
a) Aldehydes differ from Ketones in their oxidation reactions. Illustrate with one example. (1)
b) How will you prepare benzaldehyde by Gatterman-Koch reaction? (1)
c) Write the reactions of carboxylic acid with the following reagents. (Write the chemical equations)
(i) Thionyl chloride (SOCl2)
(ii) Chlorine in presence of small amount of red phosphorous.
(iii) Lithium Aluminium hydride (LiAlH4)/ether. (3)
Ans: (a) Aldehydes readily undergo oxidation and form carboxylic acid. Ketones when oxidised using strong
oxidising agent undergo C-C bond cleavage and form a mixture of carboxylic acids.
(b) Benzene when treated with CO and HCl in the presence of anhydrous aluminium chloride or cuprous
chloride, we get benzaldehyde.
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b) How will you prepare benzaldehyde by Etard's reaction? (1)
c) How will you bring about the following conversions? (Write the chemical equations)
(i) Ethanol → Ethanoic acid
(ii) Benzamide → benzoic acid
(iii) Benzaldehyde → meta nitrobenzaldehyde (3) [March 2016]
Ans: (a) Tollens’ test
(b) When toluene is oxidised using chromyl chloride (CrO2Cl2) in CS2 followed by hydrolysis (acidification), we
get benzaldehyde. This reaction is called Etard reaction.
(3)
17. Aldehydes and ketones are the compounds having >C = O group.
a) Choose the IUPAC name of the compound CH3-CH = CH-CHO
(i) Propen-1-al (ii) But-2-en-1-al (iii) Butanal (iv) But-2-en-2-al (1)
b) Complete the following reactions:
(i) HCHO + Conc. KOH ∆
(ii) CH3-CHO dil. NaOH
(iii) CH3-CHO + H2N-NH2
(iv) C6H5COCH3 Zn/Hg + HCl (4)
Ans: (a) But-2-en-1-al
(b)
(i) HCHO + Conc. KOH ∆ CH3-OH + HCOOK
(ii) CH3-CHO dil. NaOH CH3-CHOH-CH2-CH3
(iii) CH3-CHO + H2N-NH2 CH3-CH=N-NH2
(iv) C6H5COCH3 Zn/Hg + HCl C6H5CH2CH3
18. Aldehydes, ketones and acids contain >C = O group.
a) Choose the IUPAC name of the compound (CH3)2CH-COOH.
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(i) Butanoic acid (ii) Ethanoic acid (iii) 2-Methylpropanoic acid (iv) Propanoic acid (1)
b) Complete the following reactions:
(i) CH3-CH2-COOH LiAlH4/ether
(ii) CH3-CH2-COOH + SOCl2
(iii) CH3-CH2-COOH Br2/Red P
(iv) CH3-CH2-COOH + CH3-OH H+ (4) [SAY 2016]
Ans: (a) 2-Methylpropanoic acid
(b)
(i) CH3-CH2-COOH LiAlH4/ether CH3-CH2-CH2OH
(ii) CH3-CH2-COOH + SOCl2 CH3-CH2-COCl
(iii) CH3-CH2-COOH Br2/Red P CH3-CHBr-COOH
+
(iv) CH3-CH2-COOH + CH3-OH H CH3-CH2-COOCH3
19. a) The product obtained when benzene is treated with carbon monoxide and hydrogen chloride in presence of
anhydrous AlCl3 is:
i) Chlorobenzene ii) Phenol iii) Benzaldehyde iv) Benzoic acid (1)
b) How will you carry out the following conversions?
Ans: (i) Esterification: Carboxylic acids when heated with alcohols or phenols in the presence of a mineral
acid like concentrated H2SO4 or HCl gas, we get esters. Or the equation:
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(ii) Tollen’s test: When an aldehyde is heated with Tollens’ reagent, we get a bright silver mirror.
Or the equation:
R-CHO + 2[Ag(NH3)2]+ + 3OH– R-COO– + 2 Ag + 2 H2O + 4 NH3
(iii) HVZ reaction: Carboxylic acids having an α-hydrogen atom, when treated with halogen (chlorine or
bromine) in the presence of red phosphorus, we get α-halocarboxylic acids. This reaction is known as Hell-
Volhard-Zelinsky(HVZ) reaction. Or the equation:
(iv) Decarboxylation of carboxylic acid: When sodium salt of carboxylic acid is heated with sodalime (a
mixture of NaOH and CaO), we get alkanes. Or the equation:
R-COONa + NaOH CaO/∆ R-H + Na2CO3
ii) Benzoic acid reacts with NH3 to form ammonium benzoate which on heating to form benzamide.
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c) Refer the answer of the question no. 6 (d)
23. Aromatic aldehydes undergo electrophilic substitution reactions. Write the nitration reaction of benzaldehyde with
chemical equation. (2)
Ans:
(2)
Ans: (a) A is CH3-OH and B is HCOOK
(b) A is CH3-CHOH-CH2-CH3 and B is CH3-CH=CH-CH3
27. How the conversion of carbon dioxide to carboxylic acid can be effected using Grignard reagent? (2)
Ans: CO2 reacts with Grignard reagent in dry ether followed by hydrolysis, we get carboxylic acid.
28. How the conversion of an aldehyde to acetal can carry out? (Write chemical equations) (3) [SAY 2018]
Ans: Aldehyde reacts with alcohol in the presence of dry HCl to give hemiacetal (alkoxyalcohol), which
further react with one molecule of alcohol to give a gem-dialkoxy compound known as acetal.
29. Identify the products and give the name of the following reaction :
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C6H5-CHO conc. NaOH/∆ Products (2)
Ans: C6H5-CHO conc. NaOH/∆ C6H5-CH2OH + C6H5-COONa
The reaction is known as Cannizzaro reaction.
30. Explain Haloform reaction. (2)
Ans: Compounds having CH3-CO- group or CH3-CHOH- group, when treated with sodium hypohalite or
halogen in presence of NaOH, we get a haloform (CHX3). This reaction is called haloform reaction.
R-CO-CH3 NaOX R-COONa + CHX3 (where X = Cl, Br or I)
Or, X2/NaOH
31. Identify A, B and C in the following sequence of reactions :
CH3COOH + NH3 CH3COO-NH4+ ∆ A H3O+ B Br2/Red P C (3) [March 2019]
Ans: A = CH3-CONH2, B = CH3-COOH and C= CH2Br-COOH
32. Describe the following with equations : (a) Etard reaction (b) Aldol condensation (4) [SAY 2019]
Ans: Refer the answer of the question numbers 11 (a) and 16 (b)
33. Among the following which is more acidic? (a) HCOOH b) CH3CH2COOH (c) CH3COOH (d) CH3CH2CH2COOH (1)
Ans: HCOOH
34. Give a chemical test to distinguish between propanal and propanone. (2)
Ans: Propanal (being an aldehyde) gives the following tests:
i) Tollen’s test: When heated with Tollen’s reagent, Propanal gives a bright silver mirror
iii) Fehling’s test: When heated with equal volume of Fehling’s solutions A and B, Propanal gives reddish
brown ppt.
iv) Schiff’s test: Propanal restore the pink colour of Schiff’s reagent.
The above tests are not answered by propanone (being a ketone).
Iodoform (Haloform) Test: Propanone gives an yellow ppt, when treated with sodium hypoiodite or I2 in
presence of NaOH. Propanal does not give this test. [Only one test is required]
35. Explain the following reactions: (a) Rosenmund reduction (b) Cannizzaro reaction. (2 x 2 = 4) [March 2020]
Ans: (a) Rosenmund reduction : Acid chlorides react with hydrogen in presence of Pd supported on BaSO4, we
get aldehydes. This reaction is called Rosenmund’s reduction.
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(b) Carbonyl group (>CO) of aldehydes and ketones can be reduced to CH2 group in Clemmensen reduction. Name the
reagent used. (1)
Ans: (a) Tollens’ test
(b) Zinc amalgam and Conc. HCl.
39. With the help of chemical reaction explain the following name reactions:
(a) Aldol condensation (b) HVZ reaction (2 x 2 = 4) [SAY 2020]
Ans: (a) Refer the answer of the question no. 11 (a)
(b) Refer the answer of the question no. 20 (iii)
40. (i) The test to distinguish Propanal and Propanone is ………….
(A) Tollens' test (B) Lucas test (C) Hinsberg test (D) Bromine-Water test (1)
(ii) Which is more reactive towards nucleophilic addition, CH3CHO or C6H5-CHO? Give reason. (2)
Ans: (i) Tollens’ test
(ii) CH3-CHO
C6H5-CHO (Benzaldehyde) is less reactive because of the less electrophilicity of the carbonyl carbon due to
resonance. Or, due to the presence of bulky phenyl group (steric hindrance).
41. Identify the products and name the reactions.
(i) HCHO Conc.KOH/∆ ………………….. (1)
(ii) CH3CHO dil. NaOH ………………….. (1)
Ans: (i) CH3-OH
(ii) CH3-CH(OH)-CH2-CH3
42. (i) How will you prepare Benzaldehyde from the following:
A. Toluene
B. Benzene
C. Benzoyl chloride (3)
(ii) Identify the product obtained when Acetic acid is heated with P2O5. (1) [March 2021]
Ans: (i) Refer the answer of the question no. 12 (b) and 22 (b)
(ii) Ethanoic anhydride or acetic anhydride or (CH3-CO)2O
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