NUCLEUS IIT ACADEMY CHEMISTRY

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TIME- 60 Minutes Topic :Carbonyl Compound

Q.1 Carbonyl compounds are best purified by: Q.6 Match List-I with List-II and then select the correct
(1) Steam distillation. answer from the codes given below the lists:
List-I List-II
(2) Hydrolysis of sodium bisulphite adducts.
(1) RCOR'  RCH2R'
Zn / Hg
(a) Meerwein-Ponndorf
(3) Fractional crystallisation. HCl
Verley reduction.
(4) Sublimation.
C = N – NH2
(2) 
Heat
(b) Clemmensen
Q.2 Acetaldehyde oxidises: C 2 H 5 ONa
reduction
CH2 + N2
(1) Fehling's solution.
(2) Ammoniacal AgNO3 solution (3) R–C=O + Aluminium (c) Tischenko
isopropoxide reaction
(3) NaOI. R
Heat R–CH–OH
(4) All of these

Q.3 Acetaldehyde on warming with fehling solution R’

(4) RCHO + Al(OC2H5)3 (d) Wolff-Kishner
gives a red precipitate of:

 Ester
Heat
reaction
(1) Elemental copper
Codes :
(2) Cuprous oxide
1 2 3 4
(3) Cupric oxide (1) b d c a
(4) Mixture of all of the above. (2) d b a c
(3) b d a c
Q.4 What are the products formed when a mixture of (4) a c b d
benzaldehyde and formaldehyde is heated with 

conc. alkali – Q.7 CH3––CHO O H

 CH3CH(OH)CH2CHO
(1) Benzyl alcohol and formic acid In the aldol condensation of acetaldehyde
represented above, which of the following
(2) Only benzyl alcohol intermediate species are obtained ?
(3) Methyl alcohol and benzoic acid O O

(4) Only methyl alcohol (1) CH2=C–H (2) : CH2–C–H
O O
Q.5 The conversion CH3CHO –– OHC–CHO can
(3) CH3–C–CH2–CH (4) All above
be effected by:
(1) CrO3 (2) SeO2 H
Q.8 The reaction of acetone with CN– is represented as –
(3) Br2/NaOH (4) KMnO4 CH3
C=O
Step (I)
CH3
CN
CH3 .–.
C–O
+ .–. CH3
CH3 .–. CN
C–O
Step (II) Step (III) H+
CH3 CH3 CN
C
CH3 OH
In the above reaction, which is the fast
step:
(1) Step (I) (2) Step (II)
(3) Step (III) (4) All steps take place with equal ease.

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Q.9 C6H5CHO NH
  An oxime H
2 OH
2O
 A. Q.15 Ethyl cyanide is allowed to react with
The V. D. of A should be – methylmagnesium iodide and subsequently
(1) 53 (2) 52 (3) 51 (4) 50 acidified with dilute HCl. The product formed is -
(1) propanone (2) propanal
Q.10 Which of the following statements is correct: (3) butanal (4) butanone
(1) All primary alcohol give iodoform reaction.
Q.16 In the reaction
(2) All secondary alcohols give iodoform reaction.
(3) Ethanol is the only primary alkanol that CH3CHO + HCN  CH3CHOHCN
gives positive iodoform test. the product obtained is -
(4) All aldehydes with  hydrogen atoms give (1) a meso compound
positive iodoform reaction: (2) a levorotatory compound
(3) a dextrorotatory compound
Q.11 Aldehyde not containing -hydrogen atom reacts (4) a recemic mixture
with aqueous alkali to form:
Q.17 Cannizzaro reaction does not take place with -
(1) An , unsaturated aldehyde.
(2) An , unsaturated acid. (1) (CH3)3CCHO (2) CHO
 (3) Corresponding alcohol and corresponding
carboxylate anion. (3) CHO (4) CH3CHO
(4) Corresponding carboxylic acid. O

Q.12 The compounds A, B and C in the reaction sequence Q.18 In the reaction’
CH3 CH3COCH3 + SeO2  P + Se + H2O
CO  A  B H2SO

4  C are
2I Ag
Alkali  Hg  2 the product (P) is -
CH3
given by the set – (1) CH3COOCH3
(1) Iodoform, ethylene, ethyl alcohol. (2) CH3COOCH2OH
(2) Iodoform, acetylene, acetaldehyde.
(3) CH3COCHO
(3) Iodoform, propyne, acetone.
(4) Iodoform, 2-propanol, propanone. (4) CH3OCOOCH3

Q.13 The following compound is obtained on

Q.19 An alkene C7H14 on reductive ozonolysis gives
refluxing benzaldehyde with aqueos ethanolic
potassium cyanide – an aldehyde with formula C3H6O and a ketone.
(1) Benzoic acid (2) Benzyl acetate The ketone is -
(3) Cinnamic acid (4) Benzoin
(1) 2-butanone (2) 2-pentanone
Q.14 In the reaction sequence: (3) 3-pentanone (4) propanone
Dil. H2SO4,Hg2 CHCl3
CH3–CCH A B
I2 + NaOH Q.20 Identify the compounds A and B in the
C following reaction sequence
A, B and C are given by the set: 
(CH3)2C = O   a 3  b
NaCN H O
(1) CH3CH2CHO, CH3CH2CH2Cl, CHI3. HCl Heat
(2) CH3COCH3, CCl3–C–CH3 , CHI3 (1) a = CH3CO2H, b = (CH3CO)2O
O (2) a = (CH3)2C(OH)CN,
(3) CH3COCH3, CCl3–C(CH3)2 , CHI3.
b = (CH3)2C(OH)CO2H
OH
(3) a = CH3CHO, b = CH3CO2H
(4) CH3CH2CHO, CCl3–CH– CH2–CH3, CHI3.
(4) a = (CH3)2C(OH)CN, b = (CH3)2C = O
OH

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Q.21 Necleophilic addition reaction will be most Q.26 The major product obtained from photochemical
favoured in - chlorination of ethylbenzene (in excess) is
(1) CH3CHO hydrolyzed with aqueous KOH and the product
O is then oxidized with PCC. The final product
formed is
(2) CH3–CH2– CH2C–CH3 (1) PhCH2CHO (2) PhCOCH3
(3) (CH3)2C = O (3) PhCHO (4) PhCOOH
(4) CH3CH2CHO
Q.27 The reagent one would choose to transform
CH3CH2COCl into CH3CH2COCH3 is
Q.22 Benzamide on heating with bromine and caustic (1) CH3MgI (2) (CH3)2Cd
alkali gives - (3) (CH3O)2Mg (4) CH3Cl
(1) benzene
(2) methyl amino and benzene Q.28 Consider the following two reactions.
(3) aniline CHO
(4) m-Bromo-benzaldehyde SnCl 2 HCl
A  
NaBH 4
  B
100C
NO2
Q.23 Which one of the following on treatment with
The two major products (1) and (2) are
50% aqueous sodium hydroxide yields the respectively–
corresponding alcohol and acid - CH2OH CHO
(1) CH3COCH3 (2) C6H5CH2CHO
(3) C6H5CHO (4) CH3CH2CH2CHO (1) and
NO2 NH2
Q.24 Which of the following is an example of aldol CH2OH CHO
condensation ?
(2) and
(1) C6H5CHO + HCHO NaOH  C6H5CH2OH
Heat
NH2 NH2
(2) 2CH3COOC2H5   


1.C 2 H 5 ONa
CHO CH2OH
2. H 3 O
CH3COCH2COOC2H5 (3) and
(3) CH3COCH3 + (CH3)2NH 
NH2 NH2
CH3 CH3 CH2OH
CHO
CH3 – C – N – CH3
(4) and
OH
(4) 2CH3COCH3 Ba
( 
OH ) 2 NH2 NH2
CH3C(OH)(CH3)CH2COCH3
Q.29 A cyanohydrin of a compound (X) on hydrolysis
Q.25 An example of Perkin's reaction is - gives an -hydroxy acid which shows optical
(1) C6H5CHO + CH3NO2 KOH
 activity after resolution. The compound (X) is
C6H5CH=CHNO2 (1) Acetone (2) Formaldehyde
(2) C6H5CHO + CH2(COOH)2 (3) Diethyl ketone (4) Acetaldehyde

 3  C6H5CH=CHCOOH
Alc. NH
Q.30 Phenylglyoxal, [C6H5COCHO] on heating with
(3) C6H5CHO + CH3CHO  NaOH
concentrated NaOH gives
C6H5CH=CHCHO (1) C6H5COONa and CH3OH
(4) C6H5CHO + (CH3CO)2O (2) C6H5CH2OH and HCOONa
(3) C6H5CHOHCOONa
3  C6H5CH=CHCOOH
CH COONa
(4) C6H5COONa and HCOONa

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Q.31 2-Methylcyclohexanone is allowed to react with Q.36 In the reaction sequence

metachloroperoxobenzoic acid. The major 
2 CH3CHO OH  A  B ,
product formed in the reaction is the product B is:
O O O
CHO O (1) CH3–C–CH3
(1) (2)
CH3 (2) CH3–CH2–CH2–CH3
(3) CH3–CH=CH–CHO
O
H3C O (4) CH3–CH2–CH2–CH2–OH
O
(3) (4) O
Q.37 The correct sequence of reagents for the
CH3 following conversion will be :
O HO CH3
Q.32 An organic compound (1), C5H10O, reacts with
hydrazine to form a hydrazone derivative (2).
The hydrazone (2) on being heated with KOH at
HO CH3
about 180ºC, gives n-pentane. The compound (1) CHO CH3
does not respond positively to Tollens reagent (1) CH3MgBr, [Ag(NH3)2]+OH–, H+/CH3OH
and to the iodoform test. The compound (1) is (2) [Ag(NH3)2]+OH–, CH3MgBr, H+/CH3OH
O O (3) [Ag(NH3)2]+OH–, H+/CH3OH, CH3MgBr
(1) (2) (4) CH3MgBr, H+/CH3OH, [Ag(NH3)2]+OH–
H
O OH Q.38 CHO + X 3 
CH COONa
(3) (4) MeO


MeO CH = CH – COOH ,
Q.33 Cannizaro's reaction is not given by -
‘X’ is -
CHO
(1) CH3COOH (2) BrCH2  COOH
(1) CHO (2)
CH3 CHO
(3) CH3CHO (4) HCHO (3) COOH (CH3CO)2O (4) (CH3CO)2O

Q.34 Which is the major product formed when Q.39 Compounds P and R upon ozonolysis produce Q
acetone is heated with iodine and potassium and S, respectively. The molecular formula of Q
hydroxide ? and S is C8H8O. Q undergoes Cannizzaro
(1) Iodoacetone (2) Acetic acid reaction but not haloform reaction, whereas S
(3) Iodoform (4) Acetophenone undergoes halfoform reaction but not Cannizzaro
reaction.
Q.35 In the following sequence of reactions : (i) P  
i) O 3 / CH 2 Cl 2
Q
ii) Zn / H 2 O
Toluene   A SOCl
KMnO 4
2    C,
H 2 / Pd (C8 H 8 O)
BaSO 4

The product C is : (ii) R  

i) O 3 / CH 2 Cl 2
S
ii) Zn / H 2 O (C8 H 8 O)
(1) C6H5COOH (2) C6H5CH3
(3) C6H5CH2OH (4) C6H5CHO The option(s) with suitable combination of P and
R, respectively, is(are)

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 H3C
CH3 CH3
(1) and
CH3
H 3C
H3C CH3
CH3 CH3
(2) and
CH3
CH3

(3) H3C and

CH3

(4) H3C and H3C

CH3

Q.40 The reaction(s) leading to the formation of 1,3,5-

trimethylbenzene is (are)
O
Conc. H2SO4
(1) 

(2) Me heated Iron

 tube
H   
873 K

O
1) Br3 , NaOH
2) H3 O 
(3)    
3 ) Sodaime, 

O O
CHO
Zn / Hg , HCl
(4)   
OHC CHO

ANSWER KEY & SOLUTIONS

Answer-key
Ques. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 4 2 1 2 3 4 3 1 3 3 2 4 3 4
Ques. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 4 4 3 1 2 1 3 3 4 4 2 2 1 4 3
Ques. 31 32 33 34 35 36 37 38 39 40
Ans. 3 3 3 3 4 3 3 4 1,3 1,2,3

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