ALDEHYDES &

KETONES (Booklet-2)
 ALDEHYDES & KETONES

SINGLE CORRECT QUESTIONS

1. A compound has a vapour density of 29. On warming an aqueous solution of alkali, it gives a yellow
precipitate. The compound is
(A) CH3CH2CHO (B) CH3CHOHCH3 (C) CH3COCH3 (D) CH3CH2COOH
2. 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 format (D) Benzyl alcohol and methyl alcohol
3. The reagent(s) which can be used to distinguish acetophenone from benzophenone is (are)
(A) 2, 4-dinitrophenylhydrazine (B) aqueous solution of NaHSO3
(C) Benedict reagent (D) I 2 and Na2 CO3
O
||
  C6 H5  2 C  COOH The reaction is known as

4. C6 H5 CO  COC6 H5 OH

(A) Benzilic acid rearrangement (B) Aldol condensation

(C) Birch reduction (D) Beckmann rearrangement

5. The reagent that can be used to distinguish acetophenone and benzophenone is -

(A) 2, 4-dinitrophenylhydrazine (B) aqueous NaHSO3
(C) Benedict’s reagent (D) I 2 and Na2 CO3
6. A cyanohydrin of a compound (X) on hydrolysis gives an-hydroxy acid which shows optical activity
after resolution. The compound (X) is
(A) Acetone (B) Formaldehyde (C) Diethyl ketone (D) Acetaldehyde
7. Acetaldehyde on treatment with a few drops of concentrated H2SO4 gives

(A) CH3CHOHCH2CHO (B) CH3CH = CHCHO (C) (D)

8. Phenylglyoxal, C6H5COCHO, on heating with concentrated NaOH gives

(A) C6H5COONa and CH3OH (B) C6H5CH2OH and HCOONa
(C) C6H5CHOHCOONa (D) C6H5COONa and HCOONa
9. Which of the following geminaldiols is the most unstable ?

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

10. Consider the following reaction sequence.

CH3COCH3  750º
A+B
B + CH3COOH  C
The products (A), (B) and (C) are, respectively,
(A) CH4, CH2 = C = O and (CH3CO)2O (B) C2H6, CO and CH3COOCH3

(C) H2, and (D) C2H4, HCHO and HCOOCOCH3

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11. 2-Methylcyclohexanone is allowed to react with metachloroperoxobenzoic acid. The major product
formed in the reaction is

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

12. The possible number of stereoisomers that may be produced by the reaction of racemic s-butyl methyl
ketone with ethylmagnesium bromide and subsequent hydrolysis is
(A) Two (B) Three (C) Four (D) Six
13. Consider the following sequence of reactions.
1.C 2 H 5 MgBr H SO heat
1.O 3
Ketone A   B 
2 4,
 C 
 
2.H 2 O  H2 O 2.Zn ,H 2 O

The ketone (A) is

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

14. An organic compound (A), C5H10O, reacts with hydrazine to form a hydrazone derivative (B). The
hydrazone (B) on being heated with KOH at about 180ºC, gives n-pentane. The compound (A) does not
respond positively to Tollens reagent and to the iodoform test. The compound (A) is

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

Raney   2
Pt.1 equi. H
15. B    
Ni , H 2

A, B and C are:

(A) in all cases (B) in all cases

(C) in all cases (D)A: , B: , C:


 ,CN
16. 
EtOH,H 2 O
 Benzoin. The reactant is obtained by dry distillation of the calcium salts of the following pairs
(A) C6 H5CH2 COOH, HCOOH (B) C6 H5COOH, HCOOH
(C) C6 H4  OH COOH, HCOOH (D) C6H4 (NH2 )COOH, HCOOH

17. HCHO and C6 H5CHO can be distinguished by –

(A) Fehling solution (B) Tollen’s reagent (C) KMnO4 (D) All of these
NH2 OH H2 O
18. C6 H5CHO   An oxime   A. The V. D. of A should be –
(A) 53 (B) 52 (C) 51 (D) 50
19. Replacement of carbonylic oxygen is observed in the reaction –
(A) C6 H5CHO /2H (B) C6 H5CHO /H2 N – NH2
(C) C6 H5COOH /PCl 5 (D) C6 H5CHO /HCN
20. Benzyl phenyl ketone is –
(A) C6 H5COC6 H5 (B) C6 H5 – CO – CO – C6H5
(C) C6 H5CH2 – CO – C6H5 (D) C6H5CH2  – CO – CH2 – C6H5

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21. The following compound is obtained on refluxing benzaldehyde with aqueosethanolic potassium
cyanide
(A) Benzoic acid (B) Benzyl acetate (C) Cinnamic acid (D) Benzoin

22. Which of the following is not a correct statement –

(A) Acetophenone does not give a red colour precipitate with fehling’s solution
(B) Benzaldehyde gives a red coloured precipitate with Fehling’s solution
(C) Benzaldehyde gives silver mirror with Tollen’s reagent
(D) Benzaldehyde gives a black grey precipitate with mercuric chloride solution
CH3 COONa
23. Benzaldehyde  I
 cinnamic acid, ‘I’ in the above reaction is obtained by –
(A) CH3COOH  PCl 5 (B) CH3CH2 OH  K2 Cr2 O7 /H2 SO4
(C) CH3COCl  CH3COONa (D) CH3CONH2  P2 O5
24. An example of Perkin's reaction is -
(A) C6 H5CHO + CH3NO2 
KOH
 C6H5CH = CHNO2
(B) C6 H5CHO + CH2  COOH 2 
Alc.NH3
 C6H5CH = CHCOOH
(C) C6 H5CHO + CH3CHO 
NaOH
 C6H5CH = CHCHO
CH3 COONa
(D) C6 H5CHO + (CH3CO)2 O   C6H5CH = CHCOOH

25. When calcium benzoate is heated with calcium formate, the major product formed is–
(A) benzaldehyde (B) acetophenone (C) benzophenone (D) acetaldehyde

26. In the Cannizzaro reaction;2PhOH 
OH
 PhCH2OH + PhCOO–, the slowest step is–
(A) the attack of the OH– at the carbonyl group
(B) the transfer of the hydride ion to the carbonyl group
(C) the abstraction of proton from the carboxylic acid
(D) the deprotonation of PhCH2OH

27. Consider the following two reactions.

CHO

NaBH4 SnCl2-HCl
A B
<100ºC
NO2
The two major products (A) and (B) are respectively–
CH2OH CHO CH2OH CHO

(A) and (B) and

NO2 NH2 NH2 NH2
CHO CH2OH CH2OH
CHO

(C) and (D) and

NH2 NH2 NH2 NH2

28. Product (A) is:

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

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29. Which of the following pair is differentiated by iodoform test?

(A) (B)

(C) (D)

30. product (A) is:

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

31. Which of the following reagents is best used for the conversion shown below?

(A) 1. NaBH4 /2. D3O (B) 1. NaBD4 /2. H3O

(C) 1. LiAlH4 /2. D3O (D) 1. H2 /Pt / 2. D 2 O

32.

Reaction between K 1 and K 2 is:

(A) K1  K 2 (B) K1  K 2 (C) K 2  K1 (D) K1  K2  1

33. is final product when which of following is reacted with base

(A) (B)

(C) (D)
34. When acetaldehyde is treated with Fehling’s solution, it gives a precipitate of:
(A) Cu (B) CuO (C) Cu2 O (D) Cu  Cu2 O  CuO
35. In Cannizzaro’s reaction, the intermediate which is the best hydride donor is:
H H
| |
(A) C6 H 5  C  O  (B) C6 H 5  C  O  (C) (D)
| |
OH O

CHO  X   MeO

CH COONa
36. MeO 3
Ether CH CH COOH

The compound (X) is

(A) CH3COOH (B) BrCH2COOH (C)(CH3CO)2O (D) OHC—COOH

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37. Compound A (Molecular formula C3H8O) 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 and sodium acetate gives a
product C. Identify the structure of C
(A) CH3CH2CH = N  NHCONH2 (B) H3 C  C  N.NHCONH2
|
CH3
(C) H3 C  C  N. CONHNH2 (D) CH3 CH2 CH  N  CONHNH2
|
CH3
38. A mixture of benzaldehyde& 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

39. Which of the following has the most acidic hydrogen?

(A) 3-hexanone (B) 2, 4-hexanedione (C) 2, 5-hexanedione (D) 2,3-hexanedione

40. The appropriate reagent for the following transformation :

O

CH3 CH2CH3

HO
HO
is
(A) Zn(Hg), HCl (B) NH2NH2, OH– (C)H2 / Ni (D) NaBH4

MULTIPLE CORRECT QUESTIONS

1. A new carbon-carbon bond formation is possible in
(A) Cannizzaro reaction (B) Friedel-Craftsalkylation
(C) Clemmensen reduction (D) Reimer-Tiemann reaction
2. Which of the possible compound will be formed in the following sequence of reaction.
HBr Na2CO3 Hydrolysis
CH2=CH2   X 
 Y  Z
I2excess
(A) C2H5I (B) C2H5OH (C)CHI3 (D) CH3 COO 

3. Which of the following are the examples of aldolreaction?

OH CH3

(A) 2CH 3CHO 

 (B) 2CH 3COCH 3   H3C
dil. NaOH dil. NaOH
CHO CH2COCH3
H3C
OH
dil. NaOH dil. NaOH
(C) 2HCHO   CH3OH (D) C6H5CHO+HCHO   C6H5CH2OH
4. Which of the following compound undergo cannizzaro reaction?

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

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5. In which of the following intramolecularaldol condensation reaction more than two product are
possible?

(A) (B)

(C) (D)

6. Which of the following gives positive test with 2, 4-DNP?

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

7. Which of the following the following compounds reacts with NaHSO3 ?

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

8. Which of the following compounds has active methylene group?

(A) (B)

(C) (D)

9. Which of the following products is/are correctly mentioned in the following reactions.
(A) HCOH 
NaOD
 HCOONa + CH3OD (B) HCDO 
NaOH
 DCOONa + CH2DOH
(C) HCDO 
NaOEt
 DCOOEt + DCH2ONa (D) D2CO 
NaOD
 DCOONa + CD3OD

HCN(excess) H 3 O /
10. Observe the following reaction CH3  C  CH2  C  CH3     Products.
|| ||
O O
The correct statement is

(A) The product is a mixture of two compounds

(B) The product is optically inactive
(C) The product is a mixture of two chiral and one achiral stereoisomer
(D) The product is a mixture of three stereoisomers.

11. In the given reaction

2 
Hg (1) CH3 MgX K 2 Cr2 O7 /H
CH  CH 
dil. H2 SO 4
(X) 
(2) H2 O
(Y)  (Z)

(A) X is CH3CHO (B) Y is CH 3  CH  CH 3

|
OH
(C) Z is CH 3  C  CH 3 (D) Z is CH3COOH
||
O

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12. Point out the correct synthesis :
OH
O
MgBr
(1) CH3 C CH3
(A)
(2) H+
OH
MgBr
(1) Mg, ether CH Ph
(B)
(2) Ph - CHO
N N
(3) H3O+
H
H
+
(2) H
(C) PhMgBr + CH2 CH2 Ph CH2 CH2 OH
O
(D) PhMgBr + HCHO Ph CH2 OH
(2) H+

13.  - caprolactum is a starting material for the synthesis of nylon-6. The lactum can be prepared by the
reaction:

O  

MCBPA
N  OH 
H 2 SO4

 

(A) (B)

O 
NaN
3
 O 
CH3 NH 2
H 2 , Ni 

H 2 SO4
(C) (D)

14. Which of the following correctly indicate(s) the rate.

OH
CH3 CHO
CN
–
(A) CH3CH   KCN + HCl Me – – CH
–

–
CN
OH (very fast)
–

CH3 CH  O
(B) (hydrate)   H2O/H+ hydrate
(fast)
HCN /OH CH3 MgBr
(C) Cyanohydrin   C2H5CHO   Adduct formation
slow fast
(D) All of these

15. Which of the following is an example of aldol condensation?

(A) 2CH3 CHO 
dil.NaOH
 CH3CH(OH)CH2 CHO
OH
|
dil. NaOH
(B) 2CH3COCH3   H3 C  C  CH2 COCH3
|
CH3
dil. NaOH
(C) 2HCHO   CH3OH  HCOONa
dil. NaOH
(D) C6 H5CHO   C6H5CH2 OH  HCOONa

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PARAGRAPH BASED QUESTIONS
PARAGRAPH FOR NEXT FOUR QUESTIONS
Aldehydes and ketones show nucleophilic addition reactions. The -hydrogens in aldehydes and ketones
are acidic. Therefore, aldehydes and ketones having at least one -H undergo aldol condensation in the
presence of a base such as NaOH. Aldehydes having no -hydrogen undergo Cannizzaro reaction in the
presence of concentrated alkali. The carbonyl group of aldehydes and ketones can be reduced to methylene
group by Clemmensen or Wolf Kishner reduction. Aldehydes are easily oxidised to carboxylic acids by
Tollen’s reagent and Fehling solution. Functional derivatives of carboxylic acids undergo nucleophilic acyl
substitution with nucleophiles.
1. R O

O  H2N 
dil.H  H2O
 A  B
H NH
H2N
In the reaction correct statement(s) about A and B are:
I. A is optically active and dextrorotatory
II. A is racemic mixture and optically inactive
R R
B is N B is N O
H NH H NH
O NH2 NH2
III. IV.
(A) I and III (B) II and IV (C) II and III (D) I and IV
2. To convert CH2 = CH – CH2CHO to CH2 = CH – CH2COOH best reagent will be
(A) KMnO4 (B) P.C.C. (C) [Ag(NH3)2]OH (D) HIO4

3. The reactivity order of following toward nucleophilic substitution will be

O O O O O
|| || || || ||
R  C  OR  R  C  Cl R  CO CR R  C  NH 2
(I) (II) (III) (IV)
(A) I  III  IV  II (B) II  III  I  IV (C) III  IV  I  II (D) III  I  IV  II
OH
|
1. EtMgCl
4. A 
2. NH 4 Cl(aq.)
 Et  C  Et . The structure of A is:
|
Et
O
||
(A) COCl 2 (B) CH3  CH2  C  OEt
O
||
(C) CH 3  CH 2  C  CH 2  CH 3 (D)All

PARAGRAPH FOR NEXT THREE QUESTIONS

In presence of excess base and excess halogen a methyl ketone is converted first into a trihalo substituted
ketone and then into a carboxylic acid. After the trihgalo substituted ketone is formed hydroxide ion attacks
the carboxyl carbon because the trihalo methyl ion is the group more easily expelled from ktheteranhedral
intermediate. The conversion of a methyl ketone to a carboxylic acid is called a haloformreactioonbeacause
one of the product is haloform (CCHLI3) or CHI3 or CcHBr3.
O O
OH (excess) OH
R – C – CH3 R – C – CI3 R – C – CI3 R – C – OH + CI3 R – C – O + CHI3
I2 (excess)
O OH O O
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5. Which of the following compound show haloform reaction and recemisation in OD- / D2O.
O O Me Me
O Me
O O O C C C
Me Me Me Me
Me Me
(A) CH (A)2OH
(A)3CH23OH
CH CH33CH22(B)
OH (B) (B) Ph Ph(C) (C)Ph (C) (D)3 CH
(D) CH C CH
– C3 –(D)
CH– –CH ––CPh
33Ph – CH – Ph
Et Et Et
O O Et O
Et Et
Et
Ph – C – C – C – CH3 (1) I2 /OH +
6. product is
(2) H+
O Me O (3)

Me
(A) Ph  C  C  COOH (B) Ph  C  CH  Me (C) Ph  C  O  CH  Et (D) Ph  C  CH  OEt
O Et O Et O Me
O Et
O
Ph
O (1) NaIO
7. product is
(2) H ,

COOH COOH
HOOC Ph
O O O OH
(A) (B) (C) (D) Ph

PARAGRAPH FOR NEXT TWO QUESTIONS:

The conversion of aldehyde having no alpha hydrogen to a mixture of carboxylic acid and primary alcohol
is known as cannizzaro reaction. The most important feature of this reaction is the conjugate base of hydrate
of aldehyde.

8. Which step is rate determining step

(A) step I (B) step II (C) step III (D) step I & II both
9. In the given reaction final product is

(A) CH3OH + (B) HCOONa +

(C) HCOONa + (D) HCOONa +

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MATRIX MATCH QUESTIONS
1. Aldoldondensation proceeds by carbon-carbon bond formation between an enolate donor and a carbonyl
acceptor. For each of the following aldol products (1 through 4)
O O
CO2C2H5
OH
OH CH
CO2C2H5
CHO
(1) (2) (3) (4)

Match the donor and acceptor compound.

Donor Acceptor

(A) CH 2 CHO (P) CH2 = O

(B) O (Q) CHO

(C) O (R) O

CO 2C2H 5
(D) CH 2 (S) CH 2 CHO
CO 2C2H 5

2. Match the following column

COLUMN-I COLUMN-II
(A) Ph–C–H alkaline KCN Product (P) Final product formed give positive tollen test
O

O 
(1) OH
 Product
(B) 
(2) H (Q) Final product give test with 2, 4 DNP
O

(1) C2H5ONa
(C) CH3–C–OEt Product
(R) Final product react with NaHCO3 and liberated
O CO2 gas
(1) KOH
(D) Ph–CH=O Product (S) Final product react with Na and liberated H2 gas
(2) H

NUMERICAL VALUE BASED QUESTIONS

1. Compound X is a carbonyl compound with lowest molecular mass that can show positive iodoform test.
Molar mass of X compound is completely divisable by eleven.The number comes after division is

2. Sum of the number of primary alcoholic group present in open chain structure of glucose and fructose
are.

3. A compound has two isomers (A) and (B) of formula C5H10O. Isomer (A) on treating with NaOH (aq.)
gives 2, 2-dimethylpropan-1-ol and 2, 2-dimethylpropanoic acid salt. The isomer (B) on treating with
NaOH (aq.) gives 3-hydroxy, 2-propylheptanal. If product of A are X, Y and sum of carbon in X, Y are
A + B and product of B having C number of carbon then what is the value of C – A + B.

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4. An organic compound ‘A’ on treatment with ethyl alcohol gives a carboxylic acid ‘B’ and compound ‘C’.
Hydrolysis of ‘C’ under acidic conditions gives ‘B’ and ‘D’. Oxidation of ‘D’ with KMnO4 also gives ‘B’.
‘B´ on heating with Ca(OH)2 gives ‘E’ (C3H6O). E does not give Tollen’s test and does not reduce Fehling’s
solution but form a 2,4-dinitrophenyl hydrazone. How many carbon are present in product (E).

5. How many aldol products are possible (structural only) when mixture of HCHO,CH3CHO and
O
||
CH 3  C  CH 3 are reacted in dilute NaOH?

HO , 
6. CH3  CH  O  CH3CH2  CH  O   mixture ofaldols (Z) total number of aldols including
stereoisomers. Find the mole of Z?

7. Observe the following reaction sequence

(1) NaOH(1eq) (3) HCN,HCl/AlCl
2
3 (Y)  (5) NH  NHPh
Phenol    (Z)
Me (4) H3O
(2) D I
H
Answer the following questions in the given format:
P Q R S
P = Number of organic products formed in step-1
Q = Number of organic products formed in step-2 (significant products)
R = Number of organic products formed in step-3 (significant products)
S = In which step aromatic electrophilic substitution has taken place

JEE ADVANCED
1. In the following reaction sequence, the amount of D (in g) formed from 10 moles of acetophenone
is ____.
(Atomic weights in g mol 1 : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%)
corresponding to the product in each step is given in the parenthesis) [2018]

PARAGRAPH FOR NEXT TWO QUESTIONS

In the following reaction
Pd  BaSO 2 6
4  C H  i. B H
C8H6  8 8 X
H2 ii. H2O2 , NaOH, H2X
H2O
HgSO4 ,H2SO4

i. EtMgBr, H O
2 Y
C8H8O 
 ii. H ,heat
[2015]

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2. Compound X is

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

3. The major compound Y is

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

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 ANSWER KEY

SINGLE CORRECT ANSWERS

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

MULTIPLE CORRECT ANSWER

1. BD 4. ABC 7. ABC 10. AC 13. AC
2. BCD 5. AB 8. BD 11. ABC 14. AC
3. AB 6. ABCD 9. ABCD 12. ACD 15. AB

PARAGRAPH BASED ANSWERS

1. C 3. B 5. D 7. A 9. C
2. C 4. D 6. B 8. B

MATRIX-MATCH ANSWERS
1. A  S; B  P; C  Q; D  R 2. A  PQS; B  RS; C  Q; D  RS

NUMERICAL VALUE BASED ANSWERS

1. 4 2. 3 3. 0 4. 3 5. 6 6. 12 7. 1123

JEE ADVANCED
1. 495 2. C 3. D

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