Carbonyl Compounds

Nomenclature 7. Nucleophilic addition reaction will be most favoured

in :
1. The IUPAC name of Cl3CCH2 CHO is :
(a) CH3CH2CHO
(a) chloral
(b) CH 3CHO
(b) 3,3,3-trichloropropanal
(c) 1,1,1-trichloropropanal
(d) 2,2,2-trichloropropanal (c)

2. The IUPAC name of CH3COCH(CH3 )2 is : (d) (CH3) 2C = O

(a) isopropyl methyl ketone 8. Reaction of acetaldehyde with HCN followed by hydrolysis
gives a compound which shows
(b) 2-methyl-3-butanone
(a) Optical isomerism (b) Geometrical isomerism
(c) 4-methyl-isopropyl ketone
(d) 3-methyl-2-butanone (c) Metamerism (d) Tautomerism

3. The IUPAC nameof the following structure is 9. Ethanedial has which functional group(s)

(a) One ketonic (b) Two aldehydic

(c) One double bond (d) Two double bond

10. Which of the aldehyde is most reactive ?

(a) 1-hydroxy 4-methyl 3-pentanone
(a) C6H5–CHO (b) CH3CHO
(b) 2-methyl 5-hydroxy 3-pentanone
(c) HCHO (d) All the equally reactive
(c) 4-methyl 3-oxo 1-pentanol
11. Correct order of reactivity of CH3CHO, C2H5COCH3 and
(d) Hexanol-1, one-3
CH3COCH3 is
General Characteristics
(a) CH3CHO > CH3COCH3 > CH3COC2H5
4. The general formula of both aldehydes and ketones is : (b) C2H5COCH3 > CH3COCH3 > CH3CHO
(a) CnH2n + 2O (b) CnH2n O
(c) CH3COCH3 > CH3CHO > C2H5COCH3
(c) CnH2n – 2O (d) CnH2n + 4O (d) CH3COCH3 > C2H5COCH3 > CH3CHO
5. Aldehydic group can occur :
Preparation
(a) any where in the carbon chain
12. Predict the product ‘B’ in the sequence of reaction
(b) in the middle of carbon chain
(c) only at the second carbon atom of the chain
(d) only at the end carbon atom of the carbon chain
(a) CH3COONa (b) CH3COOH
6. Formalin is an aqueous solution of :
(a) formic acid (b) fluorescein (c) CH3CHO (d)

(c) formaldehyde (d) furfuraldehyde

 20. Identify the reactant X and the product Y

13. On reductive ozonolysis yields

(a) 6-oxoheptanal (b) 6-oxoheptanoic acid

(c) 6-hydroxyheptanal (d) 3-hydroxypentanal

(a) X = MgCl2 ; Y = CH3CH = CH2
14. Benzaldehyde + NaOH o
(b) X = CH3MgCl ; Y = C2H5COCH3
(a) Benzyl alcohol (b) Benzoic alcohol
(c) X = CH3MgCl ; Y = (CH3)3C – OH
(c) Hydrobenzamide (d) Cinnamic acid
(d) X = C2H5MgCl ; Y = (CH3)3C – OH
15. When but-2-yne is treated dil.H2SO4/HgSO4 the product 21. A and B in the following reactions are
formed is :

(a) butan-1-ol (b)butan-2-ol

(c) acetone (d) butanone

16. The end product in the following sequence of reaction is

1% HgSO
3
4 o A  CH MgX O (a)
HC { CH 
20% H SO
o B 
o
2 4

(a) Acetic acid (b) Isopropyl alcohol

(c) Acetone (d) Ethanol (b)

17. Which of the following compound gives a ketone with

Grignard reagent
(c)
(a) Formaldehyde (b) Ethyl alcohol

(c) Methyl cyanide (d) Methyl iodide

(d) A = RR’CH2CN, B = NaOH
Chemical Reactions
22. For C6H5CHO which of the following is incorrect
18. Dry heating of calcium acetate gives (a) On oxidation it yields benzoic acid

(a) Acetaldehyde (b) Ethane (b) It is used in perfumery

(c) It is an aromatic aldehyde

(c) Acetic acid (d) Acetone
(d) On reduction yields phenol
19. On heating calcium acetate and calcium formate, the
product formed is 23. Grignard reagent on reaction with acetone forms

(a) Tertiary alcohol (b) Secondary alcohol

(a) CH3COCH3 (b) CH3CHO
(c) Acetic acid (d) Acetaldehyde
(c) HCHO + CaCO3 (d) CH3CHO + CaCO3
24. Consider the following statement Acetophenone can be Oxidation Reactions
prepared by
28. Ketones ( ) where R = R1 = alkyl group. It can
(1) Oxidation of 1-phenyethanol
(2) Reaction of 1-phenylethanol with methyl magnesium
bromide be obtained in one step by
(3) Friedel Craft’s reaction of benzene with acetyl chloride (a) Hydrolysis of esters
(4) Distillation of calcium benzoate
(b) Oxidation of primary alcohol
(a) 1 and 2 (b) 1 and 4
(c) Oxidation of secondary alcohol
(c) 1 and 3 (d) 3 and 4
(d) Reaction of acid halide with alcohols
25. Which one of the following pairs is not correctly matched
29. The oxidation of toluene to benzaldehyde by chromyl
(a) > C = O Clemenson
 's reduction
 o > CH2 chloride is called
(b) > C = O Wolf
  Kishner reduction
   o > CHOH (a) Cannizzaro reaction (b) Wurtz reaction

(c) – COCl Rosenmund 's reduction (c) Etard reaction (d) Reimer-Tiemann reaction
  o CHO
30. Methyl ethyl ketone is prepared by the oxidation of
(d) – C { N Stephen
 reduction
 o CHO
(a) 2-propanol (b) 1-butanol
26. Which of the following compounds containing carbonyl
group will give coloured crystalline compound with (c) 2-butanol (d) t-butyl alcohol
31. The oxidation product of 2-propanol with hot conc.
HNO is

(a) Ethanoic acid (b) Propanone

(c) Propanal (d) None of these
(a) CH COCl (b) CH COCH 32. Fehling’s test is positive for
(c) CH3CO(OC2H5) (d) CH3CONH2 (a) Acetaldehyde (b) Benzaldehyde
27. Which of the following oxidation reactions can be carried
(c) Ether (d) Alcohol
out with chromic acid in aqueous acetone at 5–10°C.
33. The reaction of acetaldehyde with conc. KMnO4 gives
(a)
(a) CH3COOH (b) CH3CH2OH

(c) HCHO (d) CH OH

34. An aldehyde on oxidation gives
(a) An alcohol (b) An acid
(c) A ketone (d) An ether
35. Aldehydes are first oxidation products of :
(b)
(a) primary alcohols (b) secondary alcohols
(c) tertiary alochols (d) monohydric alcohols
36. Isopropyl alcohol on oxidation forms :
(a) acetone (b) ether
(c)
(c) acetaldehyde (d) ethylene
(d) None of these
37. Oxidation of acetaldehyde with selenium dioxide produces: 44. Which of the following reagents converts both acetaldehyde
and acetone to alkanes ?
(a) ethanoic acid (b) methanoic acid
(c) glyoxal (d) oxalic acid (a) Ni/H2 (b) LiAlH4

Reduction Reactions (c) I2/NaOH (d) Zn-Hg/conc.HCl

45. What reagent is used in the Rosenmund’s reduction ?
38. In the following reaction, product P is
(a) H2/Pd-BaSO4
(b) LiAlH4

(c) NH2NH2/KOH/CH2OH-CH2OH

(a) RCH2OH (b) RCOOH (d) Zn-Hg/HCl

(c) RCHO (d) RCH3 Condensation Reactions

46. Aldol condensation will not be observed in
39. 2o
CH3COCl Pd
H
CH3CHO + HCl.
/ BaSO 4 (a) Chloral (b) Phenyl acetaldehyde

The above reaction is called (c) Hexanal (d) Ethanal

(a) Reimer-Tiemann reaction 47. Which of the following compound will undergo self aldol
condensation in the presence of cold dilute alkali
(b) Cannizzaro reaction
(c) Rosenmund reaction (a) C6 5
CHO (b) CH3CH2CHO

(d) Reformatsky reaction (c) (d)

40. Catalyst used in Rosenmund reduction is 48. Which of the following will not undergo aldol condensation

(a) Pd/BaSO4 (b) Zn-Hg couple (a) Acetaldehyde (b) Propanaldehyde

(c) LiAlH4 (d) Ni/H2 (c) Benzaldehyde (d) Trideuteroacetaldehyde

41. Wolff-Kishner reduction is : 49. Benzaldehyde + NaOH o

(a) reduction of carbonyl compounds into hydrocarbons (a) Benzyl alcohol (b) Benzoic alcohol
(b) reduction of carbonyl compounds into alcohols (c) Hydrobenzamide (d) Cinnamic acid
(c) reduction of nitrobenzene into aniline
50. The following reagent converts C6 5
COCHO to
(d) reduction of carbohydrates into alcohols
C6H5CHOHCOONa
42. Reduction of acetonitrile in presence of SnCl2 /HCl,
followed by hydrolysis gives : (a) Aq. NaOH (b) Acidic Na2S2O3
(a) HCHO (b) CH3CHO
(c) Na2CrO4/H2SO4 (d) NaNO2/HCl
(c) CH3CH2CHO (d) CH3COCH3
51. Treatment of propionaldehyde with dilute NaOH solution
43. If pentan-2-one is reacted with NaBH4 , followed by gives
hydrolysis with D2O, the product will be :
(a) CH3CH2COOCH2CH2CH3
(a) CH3CD(OD)CH2CH2CH3
(b) CH3CD(OH)CH2CH2CH3 (b) CH3CH2CHOHCH(CH3)CHO

(c) CH3CH(OH)CH2CH2CH3 (c) CH3CH2CHOHCH2CH2CHO

(d) CH3CH(OD)CH2CH2CH3 (d) CH3CH2COCH2CH2CHO
52. Aldol condensation is : 58. Which compound does not form iodoform with alkali and iodine
(a) self condensation of aldehydes only having atleast one (a) Acetone (b) Ethanol
alpha hydrogen
(c) Diethyl ketone (d) Isopropyl alcohol
(b) self condensation of ketones only having atleast one
alpha hydrogen 59. Which compound does not gives yellow ppt. with iodine
(c) self condensation of both aldehydes and ketones having and alkali
atleast one alpha hydrogen (a) 2-hydroxy propane (b) Acetophenone
(d) self condensation of both aldehydes and ketones having
(c) Methyl ketone (d) Acetamide
no alpha hydrogen
53. Cannizzaro’s reaction is not given by : Chemical Tests
(a) CH3CHO (b) HCHO 60. Which of the following is incorrect

(c) benzaldehyde (d) triethyl acetaldehyde (a) FeCl3 is used in the detection of phenols

(b) Fehling solution is used in the detection of glucose

54. does not show aldol condensation (c) Tollen’s reagent is used in detection of unsaturation

(d) NaHSO3 is used in the detection of carbonyl compounds

because : 61. C2H5CHO and (CH3)2CO can be distinguished by testing with

(a) carbon is bounded by 3-heavy methyl groups (a) Phenyl hydrazine (b) Hydroxylamine
(b) due to the absence of D-hydrogen (c) Fehling solution (d) Sodium bisulphite
(c) it is a neutral molecule
62. Acetaldehyde cannot show
(d) due to hindrance created by methyl group for carbanion
(a) Iodoform test (b) Lucas test
Haloform Reaction
(c) Benedict’s test (d) Tollen’s test
55. Which of the following does not give iodoform test
63. Silver mirror is a test for
(a) CH3CH2OH (b) CH3OH (a) Aldehydes (b) Thio alcohols
(c) CH3CHO (d) PhCOCH3 (c) Amines (d) Ethers
56. Which of the following will not give iodoform test 64. Which of the following does not turn Schiff’s reagent to
pink
(a) Ethanal (b) Ethanol
(a) Formaldehyde (b) Benzaldehyde
(c) 2-propanone (d) 3-pentanone
(c) Acetone (d) Acetaldehyde
57. Which of the following is obtained when chloral is boiled
with NaOH

(a) CH3Cl (b) CHCl3

(c) CCl4 (d) None of these

 ANSWER KEY

1. (b) 2. (d) 3. (a) 4. (b) 5. (d) 6. (c) 7. (b) 8. (a)

9. (b) 10. (c) 11. (a) 12. (d) 13. (a) 14. (a) 15. (d) 16. (c)

17. (c) 18. (d) 19. (d) 20. (c) 21. (a) 22. (d) 23. (a) 24. (c)

25. (b) 26. (b) 27. (a) 28. (c) 29. (c) 30. (c) 31. (a) 32. (a)

33. (a) 34. (b) 35. (a) 36. (a) 37. (c) 38. (c) 39. (c) 40. (a)

41. (a) 42. (b) 43. (d) 44. (d) 45. (a) 46. (a) 47. (b) 48. (c)

49. (a) 50. (a) 51. (b) 52. (c) 53. (a) 54. (b) 55. (b) 56. (d)

57. (b) 58. (c) 59. (d) 60. (c) 61. (c) 62. (b) 63. (a) 64. (c)