Bhandarkars’ PU College kUndaPUra

CET/NEET – Chemistry – Aldehydes, Ketones and Carboxylic acids

1.Which of the following products is obtained by the oxidation of propanaldehyde?

a) Acetic acid
b) Formic and acetic acid
c) Propionic acid
d) N-Propyl alcohol

2. Which of the following will respond to Cannizzaro’s reaction

a) 2,2-Dimethylpropanal b) Acetaldehyde
c) Propinaldehyde d) Cinnamaldehyde

3. The correct order of strength of carboxylic acid is [NEET 16]

COOH COOH COOH

O
O
I II III
a. I>II>III b. II > III > I c. III > II > I d. II > I > III

4. Which of the following compounds does not react with sodium bisulphite?
a) Benzaldehyde b) benzophenone
c) acetone d) acetaldehyde
5. Consider the reactions, [NEET 2017]
Cu [Ag(NH3)2]+
X 573K
A NH OH- ,Δ Silver mirror observed
2N
(C2H 6O) HC
OH-, Δ ON
H
2

Y Z

Identify A , X , Y and Z
a. A- methoxy methane , X- ethanol, Y-ethanoic acid, Z- semicarbazide
b. A- ethanal, X-ethanol, Y-but-2-enal, Z- semicarbazone
c. A-ethanol, X- acetaldehyde, Y-butanone , Z- hydrazine
d. A- methoxymethane, X- ethanoic acid, Y- acetate ion, Z-hydrazine

6. In the reaction
𝐒𝐧𝐂𝐥𝟐+𝐇𝐂𝟏 𝑩𝒐𝒊𝒍𝒊𝒏𝒈
CH3CN+2H 𝐗 𝐘; 𝐭𝐡𝐞 𝐭𝐞𝐫𝐦 𝐢𝐬 ∶
𝐇𝟐𝐎
a) acetone b) ethyl amine
c) acetaldehyde d) dimethyl amine

7. An organic compound ‘X’ having molecular formula C5H10O yields phenyl hydrazine and
gives negative response to the iodoform test and Tollens test. It produces n-pentane on
reduction. ‘X’ could be
a. 3-pentanone b. n-amyl alcohol c. pentanal d. 2-pentanone
8. Predict the product in the given reaction
CHO

50% KOH

Cl
-
CH 2OH CH 2COO
a. CH 2OH OH
+ b.
+
Cl Cl OH OH
CH 2OH -
COO CH 2OH -
COO
c.
+ d.
+
Cl Cl OH OH
9. Lower carboxylic acids are soluble in water due to [CET 2017]
a. low molecular weight b. hydrogen bonding
c. dissociation into ions d. easy hydrolysis

10. A compound of molecular formula C8H8O2 reacts with acetophenone to form a single
cross-aldol product in the presence of base. The same compound on reaction with Conc.
NaOH forms benzyl alcohol as one of the products. The structure of the compound is [JEE-M-
17]
O O O O

a. CH3 H
b. OH OCH3
c.
d.
HO H3CO H3C

11. An organic compound X is oxidized by using K2Cr2O7 solution. The product obtained
reacts with phenyl hydrazine but does not answer silver mirror test. The compound X is [CET
16]
a. Etahnol b.propan-2-ol c. propane d. Ethanal

12. The IUPAC name of the compound

O

CH3
CH3

a. 5-formylhex-2-en-3-one b. 5-methyl -4-oxohex-2-en-5-al

c. 2-methyl -3-oxo-hex-5-enal d. 2-methyl -3-oxo-hex-4-enal
13. .Give the best reagent for the transformation of
O

CH3
CH3

HO
HO
a. Zn in dil HCl b. Zn-Hg /Conc. HCl
c. NH2-NH2 / NaOH d. alkaline KmnO4

14. Which of the following is correct order of acidity?

a) HCOOH>CH3COOH>ClCH2COOH>C2H5COOH
b) ClCH2COOH>HCOOH>CH3COOH>C2H5COOH
c) CH3COOH>HCOOH>ClCH2COOH>C2H5COOH
d) C2H5COOH>CH3COOH>HCOOH>ClCH2COOH
𝐂𝐥𝟐 𝐚𝐥𝐜.𝐊𝐎𝐇
15. CH3CH2COOH 𝐀 → 𝐁 What is B?
𝐫𝐞𝐝 𝐏
a) CH3CH2COCl b) CH3CH2CHO
c) CH2=CHCOOH d) ClCH2CH2COOH

16. Y can be obtained by Etard’s reaction, Z undergoes disproportionation reaction with

concentrated alkali. X could be [CET 14]
Ozonolysis
X Y + Z
CH3
CH CH2 CH C C CH CH CH CH3
CH3
a. b. c. d.

17. Reduction of C=O to CH2 can be carried out with

a) Catalytic reduction
b) Na/C2H5OH
c) Wolf-Kishner reduction
d) LiAlH4
18.
CO, HCl

Anhyd. AlCl3
X + HCl
compound X is
a. C6H5CH3 b. C6H5Cl c.C6H5CHO d.C6H5COOH

19. In the following sequence of reactions : [JEE-M-15]

KMnO4 SOCl2 H2 /Pd
Toluene A B C , the product C is
BaSO4

a. benzaldehyde b. benzoic acid c. propanal d. benzoyl chloride

20.Benzene carbaldehyde is reacted with concentrated NaOH solution to give the products A
and B. The product A can be used as food preservative and the product B is and aromatic
hydroxyl compound where OH group is linked to sp3 hybridised carbon next to benzene ring.
The product A and B are respectively [CET 16]
a) Sodium benzoate and cresol
b) Sodium benzoate and phenol
c) Sodium benzoate and picric acid
d) Sodium benzoate and phenyl methanol
21. Which of the following compounds will react with NaHCO3 solution to give sodium salt
and carbon dioxide?
a) Acetic acid b) n-hexanol
c) Phenol d) both (b) and (c)
22. The acid formed when propyl magnesium bromide is treated with carbon dioxide is :
a) C3H7COOH b) C2H5COOH
c) C4H7CHO d) None of these

23.The major product of nitration of benzoic acid is

a. 3-nitro benzoic acid b. 4-nitro benzoic acid
c. 2-nitro benzoic acid d. 2,4-dinitro benzoic acid

24. Compound A , C8H10O is found to react with NaOI (produced by reacting Y with NaOH)
and yields a yellow precipitate with characterstic smell. A and Y respectively. [NEET 18]
HO OH
a.H3C CH2 and I 2 b. CH2 CH2 and I 2

CH3
OH
c.H C d.
3 OH and I 2 CH CH3 and I 2

25. The organic compound A and B react sodium to give hydrogen gas. A and B react each
other to give ethyl acetate. A and B are
a. CH3COOH and CH3OH b. HCOOH and C2H5OH
c. C2H5COOH and CH3OH d. CH3COOH and C2H5OH

26. Which carbonyl compound doesnot undergo Aldol condensation ?

a. HCHO b. CH3CHO c. CH3CH2CHO d. CH3COCH3

27. During reduction of carbonyl compounds by NH2NH2 and KOH , the first intermediate is
O
a. R C N b. R C NH2 c. RCH=NH d. RCH=NNH 2

28. Benzoic acid gives benzene on being heated wit X and phenol gives benzene on being
heated with Y . Therfore X and Y are respectively
a. soda-lime and copper b. Zn dust and NaOH
c. Zn dust and soda-lime d. sodalime and zinc dust
29. An aldehyde which undergoes Cannizzaro’s reaction and redu ces Schiff’s reagent but
does not reduce Fehling’s solution is
a. CH3CHO b. HCHO c. C6H5CHO d. C6H4(OH)CHO
30. Formaldehyde can be distinguished from acetaldehyde by the use of :
(a) Schiffs reagent (b) Tollen's reagent
(c) I2/Alkali (d) Fehling's solution

Home Assignment

1.A carbonyl compound reacts with hydrogen cyanide to form cyanohydrins which on hydrolysis forms a
racemic mixture of α-hydroxy acid.The carbonyl compound is
a.Acetaldehyde b.Acetone
c.Diethyl ketone d.Formaldehyde

2.An organic compound X on treatment with acidified K2Cr2O7 gives compound Y which reacts with I2 and
sodium carbonate to form triiodomethane.The compound X can be
a.CH3OH b.CH3CHO
c.CH3COCH3 d.CH3CH(OH)CH3

3.Which is not true about acetophenone?

a.On oxidation with alkaline KMnO4 followed by hydrolysis gives benzoic acid
b.Reacts with I2/NaOH to form iodoform
c.Reacts with Tollen’s reagent to form silver mirror
d.Reacts to form 2,4-dinitrophenyl hydrazine

4.Consider the acidity of the following carboxylic acids

I.PhCOOH II.o-NO2C6H4COOH III.p-NO2C6H4COOH IV.m-NO2C6H4COOH
Which of the following order is correct?
a.I > II > III > IV b.II > IV > III > I
c.II > IV > I > III d.II > III > IV >I

5.Which one of the following acids will not form acid chloride with SOCl2?
a.C6H5COOH b.C6H5CH2COOH
c.CH3COOH d.HCOOH

6.The most reactive compound toward formation of cyanohydrins on treatment with HCN followed by
acidification is
a.Benzaldehyde b.p-Nitrobanzaldehyde
c.phenylacetaldehyde d.p-Hydroxybenzaldehyde
7.Identify the reaction which is used to obtain β-hydroxy ketone.
a.Condensation reaction b.Aldol condensation
c.Cross Cannizzaro condensation d.Cannizzaro reaction

8. The structure of the addition product formed when acetone reacts with a concentrated aqueous solution of
sodium bisulphite is
 H3C OSO 2Na H3C OSO 2H
a. C b. C
H3C OH H3C ONa

H3C SO3H OH
H3C
c. C d. C
H3C ONa H3C SO3Na

9.Name the reagent used to bring about the following transformation:But-2-ene to ethanal
a.K2Cr2O7 in acidic medium b.CrO2Cl2/H3O+
c.PCC d.O3/H2O-Zn dust

10.Conversion of benzene to acetophenone can be brought by

a.Wurtz reaction b.Wurtz-Fittig reaction
c.Friedel Crafts alkylation d.Friedel Crafts acylation

11.CH3COCl 2H Pd/BaSO4 CH3CHO + HCl

The above reaction is called
a.Reimer Tiemann reaction b.Cannizzaro reaction
c.Rosenmund reaction d.Etards reaction

12.Which of the following gases when passed through warm dilute solution of H2SO4 in presence of HgSO4
gives acetaldehyde?
a.CH4 b.C2H6
c.C2H4 d.C2H2

13.Acetophenone is prepared by the reaction of which of the following in the presence of AlCl3 catalyst
a.Phenol and acetic acid b.Benzene and acetone
c.Benzene and acetyl chloride d.Phenol and acetone

14.CH3-CH2-C≡CH HgSO4/H2SO4 A, the compound A is

a.CH3-CH2-CO-CH3 b.CH3-CH2-CH2-CHO
c.CH3-CH2-CH2-COOH .None of these

15.The reagent used in Gattermann-Koch aldehyde synthesis is

a.Pb/BaSO4 b.alkaline KMnO4
c.acidic KMnO4 d.CO + HCl

16.Acetaldehyde reacts with C2H5MgCl the final product is

a.An aldehyde b.A ketone
c.A primary alcohol d.A secondary alcohol

17.Aldehydes and ketones give addition reaction with

a.Hydrazine b.Phenyl hydrazine
c.Semicarbazide d.Hydrogen cyanide

18.C2H5CHO and (CH3)2CO can be distinguished by testing with

a.Phenyl hydrazine b.Hydroxylamine
c.Fehling solution d.Sodium bisulphate

19.The Clemmensen reduction of acetone yields

a.Ethanol b.Ethanal
c.Propane d.Propanol

20. Which of the following pairs is not correctly matched?

a) >C= O Clemmenson’s reduction >CH2

b) >C =O Wolf –Kishner reduction >CHOH

c) --COCl Rosenmund’s reduction CHO

d)--C≡N Stephen’s reduction CHO

21.When acetaldehyde is heated with Fehling’s solution it gives a precipitate of

a.Cu b.CuO
c.Cu2O d.Cu+Cu2O+CuO

22.Acetaldehyde when treated with dilute NaOH gives

a.CH3CH2OH b.CH3COOH
c.CH3-CH(OH)-CH2-CHO d.CH3-CH3

23.If formaldehyde and KOH are heated,then we get

a.Acetylene b.Methane
c.Methyl alcohol d.Ethyl formate

24.What is the name of reaction when benzaldehyde changes into benzyl alcohol?
a.Friedel-Crafts reaction b.Kolbes’s reaction
c.Wurtz reaction d.Cannizzaro reaction

25. Reaction by which benzaldehyde cannot be prepared

+CO+HCl in the presence of anhydrous AlCl 3

COOH

+ Zn/Hg and Conc. HCl

CH3
+
+ CrO 2Cl2 in CS 2 followed by H 3O

COCl

+ H2 in prsence of Pd -BaSO4
26. Statement-1. p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.
Statement-2. o- Hydroxybenzoic acid has intramolecular hydrogen bonding.
a.Statement-1is True,Statement-2 is True;Statement-2 is a correct explanation for Statement-1
b.Statement-1is True,Statement-2 is True;Statement-2 is not a correct explanation for Statement-1
c.Statement-1is True,Statement-2 is False
d.Statement-1is False,Statement-2 is True

27.When formic acid reacts with PCl5 it forms

a.Formyl chloride b.Acetyl chloride
c.Methyl chloride d.Propionyl chloride

28.Carbolic acid is
a.C6H5CHO b.C6H6
c.C6H5COOH d.C6H5OH

29.The acid which reduces Fehling solution is

a.Methanoic acid b.Ethanoic acid
c.Butanoic acid d.Propanoic acid

30.Which of the following reagents may be used to distinguish between phenol and benzoic acid?
a.Aqueous NaOH b.Tollen’s reagent
c.Molisch reagent d.Neutral FeCl3

31.Sulphonation of benzoic acid produces mainly

a.o-sulphobenzoic acid b.m-sulphobenzoic acid
c.p-sulphobenzoic acid d.o- and p-sulphobenzoic acid

32.A liquid was mixed with ethanol and a drop of concentrated sulphuric acid was added. A compound with
a fruity smell was formed. The liquid was
a.CH3OH b.HCHO
c.CH3COCH3 d.CH3COOH

33.Benzoic acid has higher molecular weight in benzene and less in water because
a.Water has lower freezing point and higher boiling point than benzene.
b.It dissociates to a greater extent in benzene than in water.
c.It associates in water and dissociates in benzene.
d.It dissociates in water and associates in benzene.

34.Lactic acid molecule has

a.One chiral carbon atom b.Two chiral carbon atoms
c.No chiral carbon atom d.Three chiral carbon atoms

35.Right order of acidic strength is

a.CH2ClCOOH > HCOOH > C2H5COOH > CH3COOH
b.CH2ClCOOH > HCOOH > CH3COOH > C2H5COOH
c.C2H5COOH > CH3COOH > HCOOH > CH2ClCOOH
d.HCOOH > CH2ClCOOH > CH3COOH > C2H5COOH
36.Nitration of benzoic acid gives
a.3-nitrobenzoic acid b.2-nitrobenzoic acid
c.2,3-dinitrobenzoic acid d.2,4-dinitrobenzoic acid

37.X is heated with soda lime and gives ethane. X is

a.Ethanoic acid b.Methanoic acid
c.Propanoic acid d.Either a or c

38.When CH2=CH-COOH is reduced with LiAlH4, the compound obtained will be

a.CH3-CH2-COOH b.CH2=CH-CH2OH
c.CH3-CH2-CH2OH d.CH3-CH2CHO

39.When propionic acid is treated with aqueous sodium bicarbonate CO2 is liberated.The C of CO2 comes
from
a.Methyl group b.Carboxylic acid group
c.Methylene group d.Bicarbonate

40.Identify the correct order of boiling points of the following compounds

1.CH3CH2CH2CH2OH, 2.CH3CH2CH2CHO, 3.CH3CH2CH2COOH
a.1>2>3 b.3>1>2
c.1>3>2 d.3>2>1

LiAlH4 PCl5 Alc.KOH

A C
41.In the reaction CH 3COOH B the product C is
a. acetaldehyde b. Acetylene c. Ethene d. Acetyl chloride

42. When acetaldehyde reacts with PCl5 the resulting compound is

a.Ethyl chloride b.Ethylene chloride
c.Ethylidene chloride d.Trichloro acetaldehyde

43.Hydrolysis of acetamide produces

a.Acetic acid b.Acetaldehyde
c.Methylamine d.Formic acid

44.Sodium acetate reacts with acetyl chloride to form

a.Acetic acid b.Acetone
c.Acetic anhydride d.Sodium formate

45.The reaction of acetamide with water is an example of

a.Alcoholysis b.Hydrolysis
c.Ammonolysis d.Saponification

46.The reagent which does not give acid chloride on treating with a carboxylic acid is
a.PCl5 b.Cl2
c.SOCl2 d.PCl3

47.The compound most suitable for the preparation of cyanohydrin is

a.C2H5COOH b.C6H5NH2
c.C2H5COC2H5 d.C2H5-C2H5

48.In the following reaction order, B is

CH3CH2COOH P/Br2 A alc.KOH B
a.CH2=CH-COOH b.CH3-CH(Br)COOH
c.CH3CH2COBr d.CH3CH2CH2OH

49.Clemmensen’s reduction will convert cyclohexanone into:

a.Cyclopentanone b.Cyclohexane
c.n-Hexane d.Benzene

50.The vapours of ethyl alcohol are passed over red hot copper at 573K to form:
a.Methane b.Formaldehyde
c.Acetone d.Acetaldehyde

51.Heating sodium benzoate with soda lime gives

a.Benzoic acid b.Benzaldehyde
c.Toluene d.Benzene

52.Hydrolysis of benzonitrile gives:

a.Benzylamine b.Phenol
c.Benzene d.Benzoic acid

53.CH3COOH LiAlH4 X Cu/300OC Y dilute NaOH Z

In the above reaction, Z is
a.Aldol b.Ketol c.Acetal d.Butanol

54.The carboxylic acid which does not undergo Hell Vohlard Zelinsky reaction is:
a.CH3COOH b.(CH3)2CHCOOH
c.CH3CH2CH2CH2COOH d.(CH3)3CCOOH

55.The correct order of increasing acid strength of the compounds:

A.CH3COOH B.MeOCH2COOH
C.CF3COOH D.(Me)2CHCOOH
a.d < a< c < b b.d< a < b < c
c.a < d < c < b ` d.b < d< a < c

56. Trichloroacetaldehyde was subjected to Cannizzaro’s reaction by using NaOH. The mixture of the
products contains sodium trichloroacetate and another compound. The other compound is :
a. 2,2,2-Trichloroethanol
b. Trichloromethanol
c. 2,2,2-Trichloropropanol
d. Chloroform

57.Ethyl magnesium bromide adds on CO2 which on hydrolysis gives:

a.methanoic acid b.butanoic acid
c.propanoic acid d.ethanoic acid
58.Which one of the following undergoes reaction with 50% NaOH Solution to give
the corresponding alcohol& acid ?
a) Phenol b) Benzoic Acid c) Butanal d) Bezaldehyde

59.Acetone reacts with Grignard reagent to form

a)30-alcohol b)20 alcohol c) Ether d)No Reacion

60.A comound on dehydrogenation gives a ketone. The original compound is

a.tertiary alcohol b.carboxylic acid c.primary alcohol d.secondary alcohol
***************

SOLUTIONS

1.a acetaldehyde
2.d CH3CH(OH)CH3 K2Cr2O7 CH3-CO-CH3

3.c Acetophenone is ketone.It does not reacts with Tollen’s reagent to give silver mirror.

4.d -NO2 group at any position shows electron withdrawing effect. Thus, acidic strength
increased.But o-nitrobenzoate ion is stabilized by intramolecular H-bonding.Its acidic
strength is maximum.

5.d HCOOH, Because HCOCl is unstable.

6.b Addition of HCN to a carbonyl compound is a nucleophilic addition reaction.. –NO2

group being electron withdrawing increases the polarity of carbonyl carbon and thus, makes
the C=O group of benzaldehyde more reactive towards HCN.

7.b Aldol condensation

8.d

9.d

10.d Friedel Crafts acylation

11. c. CH3COCl 2H Pd/BaSO4 CH3CHO + HCl

12. d
13. c C6H5 + CH3COCl only AlCl3 C6H5COCH3 + HCl

14. a

15. d

16. d

17. d
18. c C2H5CHO + 2Cu2+ 5OH- Cu2O + 3H2O C2H5COO –
CH3COCH3 + 2Cu2+ + 5OH- No reaction

19. c

20. b Wolff-Kishner reduction does not convert > CO to CHOH but converts it to > CH2
21. c CH3CHO + 2Cu2+ + OH- Cu2O- + CH3COOH
22. c 2CH3CHO dil. NaOH CH3CH(OH)CH2CHO
23. c HCHO + HCHO KOH HCOOK + CH3OH

24. d Cannizzaro’s reaction involve self-oxidation and self-reduction.

25. b
26. c CH3CHO + PCl5 CH3CHCl2 + POCl3
27. a HCOOH + PCl5 HCOCl + POCl3 + HCl

28. d Phenol was discovered by Runge in the middle oil fraction coal-tar distillation and named
it ‘carbolic acid’ or phenol containing 5% water in liquid at room temperature and it is
termed as carbolic acid.
29. a Methanoic acid resembles with aldehyde due to its structure. So it reduces Fehling
reagent.

30. d

Reagent Phenol Benzoic acid Conclusion

a.Aqueous Salt formation Salt formation No specific colour
NaOH change
b.Tollens reagent No effect No effect
c.Molisch No effect No effect
reagent
d.Neutral fecl3 Violet colour Buff-coloured Thus, FeCl3 can be
precipitate used to make
distinction

31. b C6H5COOH + Conc. H2SO4 COOH

+ H2O

SO3H

32. d A liquid + C2H5OH Conc. H2SO4 Compound

Fruity smell is the characteristic property of ester, thus the above reaction leads

to the formation of ester.

CH3COOH + C2H5OH Conc. H2SO4 CH3COOC2H5 + H2O

The reaction is called esterification.

33. d C6H5COOH + H2O C6H5COO - + H3O +

In benzene solution

C6H5COOH O …… H -- O
C -- O – H …… O = C

34. a Lactic acid has one asymmetric (chiral) carbon atom, hence it has (21 = 2) optical
isomers .

35. b
36. a

37. c X NaOH/CaO C2H6

C2H5COOH NaOH/CaO C2H6

38. b CH2 = CH – COOH LiAlH4 CH2 = CH – CH2 OH + H2O

39. d CH3CH2COOH (aq) + NaHCO3 (aq) CH3CH2COONa + CO2 + H2O

40. b -COOH group shows strong hydrogen bonding so it forms dimer and have more boiling
point than –OH group. While -CHO group does not form hydrogen bond.

41. c

42. d

43. a CH3CONH2 H2O CH3COOH + NH3

44. c CH3COONa + CH3COCl NaCl + CH3COOCOCH3

45.b. The reaction of acetamide with water is an example of hydrolysis.

46.b

47.c. Ketones react with HCN to form addition product, known as cyanohydrin compounds.

48.a

49.b cyclohexane

50.d CH3CH2OH Cu/573K CH3CHO

51.d. It is decarboxylation reaction.

52.d C6H5CN H2O C6H5COOH

53.a X=CH3CH2OH Y=CH3CHO Z=CH3-CH(OH)-CH2-CHO

54.d

55.b d<a<b<c

56.a

57.c C2H5MgBr + CO2 Hydrolysis C2H5COOH + Mg(OH)Br

58.d Benzaldehyde(do not contain α-hydrogen atoms) and undergoes Cannizzaro reaction.

59.b

60.d. Secondary alcohol

*****************