CHEMISTRY

CARBONYL COMPOUND (CPP-1)

Ex - 1
1. Which one of the following is mixed ketone (Aliphatic & aromatic):
O O O O
|| || || ||
(A) CH3  C  CH3 (B) CH3  CH2  C  CH3 (C) Ph  C  CH3 (D) CH3  C6H4  C  CH2Ph

2. In which of the following reactions product will be aldehyde?

(A) (i) O3 (B) (i) HBr/R2O2
H 3C C C C 2 H5 H3 C CH CH2
(ii) H2O (ii) aq.KOH
H3C CH3
(iii) PCC
(C) (D) HOH/HgSO4 /H2 SO 4
B2H6
C CH H3 C C CH
H3C (kucherov reaction)
NaOH, H2O2

3. Two isomeric ketones, 3 – pentanone and 2 – pentanone can be distinguished by:

(A) I2 / NaOH (B) NaSO3H (C) NaCN / HCl (D) 2,4  DNP

4. Stability of hydrates of carbonyl compounds depends on:

(A) Steric hindrance (B) Presence of – I group gem diol carbon
(C) Intramolecular hydrogen bonding (D) angle strain in carbonyl compound

5. Which of boding give positive test with 2, 4 – DNP?

O O O
|| || ||
(A) CH3  C  H (B) CH3  C  CH3 (C) CH3  C  OH (D) CH3  CH2  OH

6. Fehling solution gives red precipitate with.

(A) Aromatic aldehyde (B) Aliphatic aldehyde (C) ketones (D)   hydroxy ketones

7. Silver mirror test with Tollen’s reagent is given by:

(A) C6H5 CHO (B) Ph  CH2  CHO
(C) C6H5  CH2  C  CH2 OH (D) CH3 CHO
||
O
8. Which one of the following compounds will not give aldol:
(A) Acetaldehyde (B) Formaldehyde (C) Pivaldehyde (D) Crotonaldehyde

9. Schiff’s reagent gives pink colour with:

(A) Acetaldehyde (B) Ph – CH3 (C) Acetic acid (D) Methyl acetate

10. Which of the following compounds will give positive Tollen’s test
(A) CH3 CHO (B)

O OH

(C) H3C CH2 CH2 CH2 CH OCH3 (D) OCH3

OH H 3C HC
OCH3

11. Mixture of Ph – CHO & HCHO is treated with NaOH then Cannizzaro reaction involves:
(A) Oxidation of HCHO (B) Reduction of HCHO
(C) Oxidation of Ph - CHO (D) Reduction of Ph - CHO
12. PhCHO  HCHO  Conc KOH

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Correct statement regarding reaction will be.
(A) It is an example of redox reaction (B) H CHO is oxidised
(C) It is cross Cannizzaro reaction (D) Ph – CHO is reduced

Paragraph for Question Nos. 13 to 15: -

Carbonyl group show characteristic reaction of nucleophilic addition in which nucleophile attack in rate determing
step on carbonyl carbon.
13. Which pH is suitable for oxime formation
(A) 4 - 5 (B) 1 - 2 (C) 8 – 10 (D) 12 – 14

14. Which of the reactant show geometrical isomerism when it react with hydrazine (NH 2 – NH2)
(A) O ((B) O (C) O (D) O

H H
15. CH O
PCl5 PhMgBr NH2 - NH2
w x y
C OH
O

Identify final product ‘y’ of the above given reaction:

(A) (B) (C) (D) N
N N

N
Ph
Ph Ph Ph

16. Match the following:

Column I Column II
(A) O (p) An enamine will form
H+
+

N
H
(B) OH (q) Schiff base will form

HN PH
H+

(-H 2O)

(C) O NH2 (r) Hydrazone will form

(D) O (s) Product form will undergo Lassigne test

+ H2N NH2

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Ex - II
Single choice Questions:
1. The reagent with which both acetaldehyde and acetone react easily is
(A) Tollen reagent (B) Schiff reagent (C) Grignard reagent (D) Fehling reagent

2. The Cannizzaro reaction is not given by

(A) trimethyl acetaldehyde (B) acetaldehyde
(C) benzaldehyde (D) formaldehyde

3. When acetaldehyde is heated with Fehling solution, it gives a precipitate of

(A) Cu (B) CuO (C) Cu2O (D) Cu  Cu2 O  CuO

4. The formation of cyanohydrins from a ketone is an example of;

(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic susbstitution (D) Electrophilic substitution

5. m – chlorobenzaldehyde on reaction with conc. KOH at room temperature gives:

(A) Potassium m – chlorobenzoate and m - hydroxybenzaldehyde
(B) m – hydroxybenzaldehyde and m – chlorobenzyl alcohol
(C) m – chlorobenzyl and m – hydroxybenzyl alcohol
(D) Potassium m – chlorobenzoate and m – chlorobenzyl alcohol

6. Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives:

(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol

7. An organic compound C3H6O does not give a precipitate with 2, 4- Dinitrophenyl hydrazine reagent and
does not react with metallic sodium. It could be:
(A) CH 3 CH2CHO (B) CH3 COCH3
(C) CH2  CH  CH2 OH (D) CH2  CH  O  CH3

8. Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane

9. In the reaction, P is
H3 C
CO P + Se + H2O
H3 C
(A) CH3 COCHO (B) CH3 COOCH3
(C) CH3 COCH2 OH (D) None

10. In the Cannizzaro reaction given below, 2Ph – CHO 
OH
 Ph  CH2OH  PhCO2 the slowest step is:
(A) the attack of OH- at the carbonyl group
(B) the transfer of hydride to the carbonyl group
(C) the abstraction of proton from the carboxylic acid
(D) the deprotonation of Ph  CH2OH
11. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe
12. In a Cannizzaro reaction the intermediate which is the best hydride donor is:
(A) H (B) H
- -
H5 C6 C O H5 C6 C O
-
OH O
(C) H (D) H
- -
O O
- -
O O
ON 2 H3CO
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13. CH3 CHO  H2NOH 
 CH3  CH  N  OH. The above reaction occurs at:
(A) pH  1 (B) pH  4.5 (C) Any value of pH (D) pH  12

14. Among the following compounds, which will react with acetone to give a product containing
C N ?
(A) C6H5NH2 (B)  CH3 3 N
(C) C6H5NHC6H5 (D) C6H5NHNH2

15. Which of the following will react with water:

(A) CHCl3 (B) Cl3CCHO (C) CCl4 (D) ClCH2CH2Cl

16. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol

17. 1 – propenol & 2 – propenol can be best distinguished by:

(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acidic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2SO4 followed by reaction with Fehling

18. Compound A (molecular formula C3H3O) is treated with acidified potassium dichromate to form a product B
(molecular formula C3H6O). B forms a shining silver mirror on warming with ammoniacal silver nitrate. B
when treated with an aqueous solution of H2NCONHNH2. HCl and sodium acetate gives a product C.
Identify the structure of C.
(A) CH3 CH2 CH  NNHCONH2 (B) H3C C NNHCONH 2
H3C
(C) H3C C NCONHNH 2 (D) CH3 CH2 CH  NCONHNH2
H3C
19. CHO OHC

(i) NaOH (excess) 100 °C

(ii) H+/H2O

CHO OHC

any one of the products formed is: CH2OH HOH2C

(A) COOH HOOC (B)

COOH HOOC CH2OH HOH2C

(C) CH2OH HOOC (D) O

COOH HOH2C
O

20. Which of the following compounds will give a yellow precipitate with iodine and alkali?
(A) 2 – hydroxyl propane (B) Acetophenone
(C) Methyl acetate (D) Acetamide

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2 
21. Ph  C  C  CH3 
Hg /H
A
A is
(A) O (B) Ph (C) O (D) Ph
Ph O Ph OH
H 3C H3C
H3 C H3 C

22. COOH

CHO
CH3COONa
+ X

OMe OMe

What is X?
(A) CH3COOH (B) BrCH2, COOH (C) (CH3CO)2O (D) CHO - COOH

23. How will you convert butane – 2 – one to propanoic acid?

(A) Tollen reagent (B) Fehling solution (C) NaOH/I2/H+ (D) NaOH/NaI/H+

24. The smallest ketone and its next homologue are reacted with NH2OH to form oxime.
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active

25. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product?
O
C
O

CH2

(A) COOCH3 (B) COOH

COOH CHO

(C) CHO (D) COOH

CHO COOH
26. Cyclohexane on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E
on further treatment with aqueous KOH yields compounds F. Compound F is
(A) (B) (C) (D) CO2H
CHO CHO COOH
CO2H

27. Statement -1: Glucose gives a reddish – brown precipitate with Fehling’s solution.
because
Statement – 2: Reaction of glucose with Fehling’s solution gives CuO and gluconic acid.
(A) Statement – 1 is True, Statement – 2 is True; Statement – 2 is a correct explanation for Statement – 1.
(B) Statement – 1 is True, Statement -2 is True; Statement 2 is NOT a correct explanation for Statement –
1.
(C) Statement – 1 is True, Statement – 2 is False.
(D) Statement – 1 is False, Statement – 2 is True.

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28. The number of aldol reaction(s) that occurs in the given transformation is:
OH OH

CH3 CHO  4HCHO  conc.aq.NaOH

HO OH
(A) 1 (B) 2 (C) 3 (D) 4

29. The major product H in the given reaction sequence is


95%H2 SO4
CH3  CH2  CO  CH3 
CN
 G 
Heat
H
(A) H3C CH C COOH (B) H3C CH C CN
CH3 CH3

(C) OH (D) H3C CH C CO NH2

H3C CH2 C COOH CH3
CH3
30. Which of the following carboxylic acids undergoes decarboxylation easily?
(A) C6H5 COCH2 COOH (B) C6H5 COCOOH
(C) C6H5 CH  OH COOH (D) C6H5 CH NH2  COOH

31. In which of the following reaction diastereomer will form?

(A) O (B) O (C) O (D) O

LiAIH4 LiAIH4 LiAIH4 LiAIH4

32. Match the compounds/ion in column I with their properties/ reaction in column II. Indicate your answer by
darkening the appropriate bubbles of the 4  4 matrix given in the ORS.

Column I Column II
(A) C6H5 CHO (p) Gives precipitate with 2, 4 – dinitrophenylhydrazine
(B) CH3 C  CH (q) Gives precipitate with AgNO3
(C) CN- (r) is a nucleophile
(D) I- (s) is involved in cyanohydrins formation

33. Match the compounds/ion in column I with their properties/ reaction in column II. Indicate your answer by
darkening the appropriate bubbles of the 4  4 matrixes given in the ORS.

Column I Column II
(A)   (p) Sodium fusion extract of the compound gives Prussian
H2N  NH3 Cl blue colour with FeSO4
+ -
(B) N H3I (q) Gives positive FeCl3 test
HO
COOH

(C) + -
(r) Gives white precipitate with AgNO3
HO N H3Cl

(D) + -
(s) Reacts with aldehydes to form the corresponding.
O 2N NH N H3Br hydrazone derivative

NO2

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Paragraph for Question No. 34 to 36:
A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds J and
K Compound J upon reaction with KOH gives benzyl alcohol and compound L, whereas K on reaction with KOH
gives only M.
O
H3 C
Ph
M =

Ph H

34. Compound H is formed by the reaction of

(A) O (B) O
+ PhMgBr + PhCH2MgBr
Ph CH3 Ph CH3

(C) O (D) O Me
+ PhCH2MgBr +
Ph H Ph H Ph MgBr

35. The structure of compound I is

(A) Ph CH3 (B) H3C Ph (C) Ph CH3 (D) H3C CH3

H Ph H Ph H CH2Ph Ph H

36. The structures of compounds J, K and L, respectively, are

(A) PhCOCH3 ,PhCH2COCH3 and PhCH2COO K  (B) PhCHO, PhCH2 CHO and PhCOO K 
(C) PhCOOCH3 , PhCH2CHO and CH3COO K  (D) PhCHO,PhCOCH3 and PhCOO K 

Paragraph for Question No. 37 to 38:

An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through
the following sequence of reaction, in which Q is an intermediate organic compound.
i  conc.H2SO4 O
 
i dil.H SO /HgSO  catalytic amount
P 
 ii NaBH4 / ethanol  Q 
2 4 4
 ii  O3 2
 C6H10  C
 iii  Zn/H2O
H3 C CH3
37. The structure of compound P is:
(A) CH3  CH2 CH2CH2  C  C  H (B) H3 CCH2  C  C  CH2 CH3
(C) H3C (D) H3C
H C C C CH3 H3C C C C H
H3C H 3C

38. The structure of the compound Q is:

(A) H C HO (B) H C HO
3 3
H C C C CH2CH3 H C C CH3
H3 C H H3 C H

(C) H3C HO (D) HO

H C CH2 CH CH3 H3C CH2 CH2 CH CH2CH3
H3 C
Paragraph for Question No. 39 to 40:
Two aliphatic aldehydes P and Q react in the presence of aqueous K2CO3 to give compound R, which upon
treatment with HCN provides compound S. On acidification and heating. S gives the product shown below:

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H3C OH
H3C

O O
39. The compounds P and Q respectively are -
(A) CH3 (B) CH3
H3 C H H H
CH H C CH H C
H3 C C H3 C C
and and
O O
O O

(C) H3C CH2 H3 C H (D) H3C CH2 H H H

H C C
HC C HC C
and and
O O
CH3 O CH3 O

40. The compound R is

(A) O (B) O

H3 C C H3 C C
C H C H
H3 C H3 C
CH
H 2C H 3C OH
OH
(C) CH3 O (D) CH3 O
CH C CH CH
H3 C HC H H3 C HC H

CH2 CH
H3 C OH
OH
41. The compound S is
(A) CH3 O (B) O

CH H3C C
C C H
H3 C HC H H 3C
H2 C
CH2 CN
CN

(C) CH3 CN (D) CN

CH CH H3 C CH
H3 C OH C OH
HC H3 C
H 2C
CH2
OH
OH

Ex - III
Subjective:

1. Acetophenone on reaction with hydroxylamine – hydrochloride can produce two isomeric oximes. Write
structures of the oximes.

2. Five isomeric para – disubstituted aromatic compounds A to E with molecular formula C 8H8O2 were given
for identification. Based on the following observations, give structure of the compounds.
(i) Both A and B form a silver mirror with Tollen’s reagent; also, B gives a positive test with FeCl3 solution
(ii) C gives positive iodoform test.
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(iii) D is readily extracted in aqueous NaHCO3 solution
(iv) E on acid hydrolysis gives 1, 4 - dihydroxybenzene

3. HCl
C6H12 C6H13Cl + (C)
(A) (B)

A/c. KOH ozonolysis

(D) (E)
(-HCl)

 A  
ozonolysis
F    G  
NaOH
 HCOONa  1o alcohol
(D) is isomer A. E gives negative test with Fehling solution but gives iodoform test. F and G gives Tollen’s
test but do not give iodoform test. Identify A to G.

4. Give major products A, B, C and D in following reaction sequence.

CH2 Cl

  A  

 B  
H3 O 
  C    D 
i NaOEt /EtOH (i)SOCl2

KCN
DMF (ii)PhCHO/  (ii)CH3 NH2

5. Which of the following disaccharide will not reduce Tollen’s reagent?

CH2OH CH2OH HOH2C CH2OH
(a) H O (b) OH O OH
OH O H H O O H H
H
H OH H OH H OH OH

O H H O H
H
OH H OH H OH H H OH

(Q) (P)
6. OH
H+,  (i) O3 aq.KOH
X Y (Z)
(ii) Zn/CH3COOH  major product

Identify X, Y and Z.

7. In the scheme given below, the total number of intramolecular aldol condensation products formed from ‘Y’
is
1.O3 1. NaOH (aq)
Y
2. Zn, H2O 2. heat

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Answer (ex - I)
1. CD 2. BC 3. AB 4. ABCD 5. AB 6. BD 7. ABCD

8. BC 9. A 10. ABC 11. AD 12. ABCD 13. A 14. D

15. C

16. A  P,S; B  Q,S; C  Q,S; D  R,S.

Answer (ex - II)

1. C 2. B 3. C 4. B 5. D 6. B 7. D

8. D 9. A 10. B 11. A 12. D 13. B 14. A

15. B 16. A 17. C 18. A 19. C 20. AB 21. A

22. C 23. C 24. B 25. C 26. A 27. C 28. C

29. A 30. A 31. ABD

32. A  p,s; B  q,r; C  q,r,s; D  q,r.

33. A  r,s; B  p,q; C  p,q,r; D  p,s. or A  r; B  p,q; C  p,q,r; D  p.

34. B 35. A 36. D 37. D 38. B 39. B 40. A

41. D

Answer (ex - III)

1. H5C6 C CH3 H5 C 6 C CH3
and
N OH HO N
syn anti(isomers)

O
2.
CHO CHO CH2CHO C CH3 COOH O CH CH2

(a) or (b) (c) (d) (e)

OCH3 CH2OH OH OH CH3 OH

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3. Me3 C  CH  CH2 
HCl
 Me2 C  CHMe2  Me3 C  C H  Me
(A) | |
Cl Cl
(B) (C)

O
O3
CHMe2 alc.KOH
Me 2 C Zn, H2O

Cl (E)
(D)
 A   HCHO Me3 C  CHO 
Ozonolysis
F  G
NaOH


HCOONa  Me3 C  CH2OH 10 alcohol 
H3CHNOC
4. CN COOH
HC C
CH C CH C
CH2 CN

(a) (b) (c) (d)

5. In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that why
Tollen’s solution cannot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce
Tollen’s solution.

6. O
O
(X) CH3
(Y) H3C C (CH2)4 CH O, (Z)
,

CH3

7. 1

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