Aldehydes and Ketones: Topic

 JEE (ADVANCED) - RRB
TOPIC
ALDEHYDES AND KETONES
8
SECTION - I : STRAIGHT OBJECTIVE TYPE
– – 
 A  B 
 C
OH H
8.1 PhCOCHBr2 
OH
The compound 'C' is

(A) PhCH(OH)CHO (B) PhCH(OH)COOH
(C) PhCO C Br2 (D)

|
H
8.2 The product/s of the following reaction is
PhCO H
  
3

O O
Ph || Ph ||
C – C – O – Me C – O – C – Me
(A) (B)
Me Me
H H
O
Ph ||
(C) (D) C = O + HO – C – Me
Me
8.3 Which step is not feasible in the following loop ?
Br
EtOH, H |
CH2(Br)CH2CHO   
 
a CH2 — CH2CH (OEt )2
H O, H
CH2=CHCHO  2   CH2=CHCH(OEt)2
c
(A) step - a (B) step - b (C) step - c (D) step - d
254

 
8.4  P 
OH H3 O
 Q
2Q 2 
  R
H SO
4
The product R is :
(A) CH3 CH(OH)COOH (B)
(C) CH3 CH = CH – COOH (D) CH3 CH C CH3
O OH
  B Conc
  C Zn – Hg
8.5 CH3 – C – (CH2)4 – C – CH3 Ph – MgBr
A 
|| || .HCl
O O
The product ‘C’ is %
Ph O Ph Ph
Ph
(A) (B) (C) (D)
CH3 COONa
8.6 PhCHO + (CH3CO)2O    A  B
HBr
The product B is
(A) PhCH = CHCH2Br (B)
(C) PhCH2 CH(Br) COOH (D) PhCH = CH – COBr
8.7 The number of stereoisomeric products formed in the following reaction is
HO
+   
Ether 2
(A) 1 (B) 8 (C) 4 (D) 2
255

8.8 The end products of following reaction would be,
(A) + HCOONa (B) + HCOONa
(C) (D) + CH3OH
8.9 In which of the following compounds O18 exchange can be observed on keeping it in H2O18
(A) (B) (C) (D)
8.10 What will be the product of the following reaction

O O
|| ||
H / 
+ H3 C  C  (CH2 )2  C  CH3  
(A) (B) (C) (D)
8.11 The possible number of stereoisomers of the product of following reaction would be :
Ph – CH = CH – CH – CHO
| NH2OH
CH 3   

(A) 2 (B) 4 (C) 6 (D) 8
256

8.12 Which of the following ketone racemises in aqueous solution containing some acidic or basic impurities.
(A) (B)
(C) (D)
8.13 The final product (X) of the following reactions would be

. PCl  
5     (X)
Br2 / Fe
C 6H5  C  C 6H5    
NH2OH HCl
(1) ( 2) (3)
||
O
(A) (B)
(C) (D)
 
CH3 C C Na H , Pd CaCO 3 Al O 3
  X 2 Y 2      Z 2 
 W, W is :
H O
8.14 CH3COCH3 
(A) CH2=CH—CH=CH2 (B) CH3 – CH  CH — CH  CH2
CH3
|
CH  CH — C  CH2
(C) | (D) CH3–CH=CH–CH=CH–CH3
CH3
257

8.15
Identify X, Y, Z and W.
X Y Z W
Br CH3 CH3
C6H5 – C = CH – (CH2)2OH |
(A) | C6H5 – C – (CH2)3 – OH
CH3 |
CH3 OH
Br CH3
| CH3
C6H5 – C = CH – (CH2)2OH Br
(B) | C6H5 – C – (CH2)3 – OH
|
CH3
CH3
Br CH3
| CH3
(C) C6H5 – C = CH – (CH2)2OH C6H5 – C – (CH2)3 – Br
Br
|
CH3 |
CH3
Br CH3 CH3
| Br
(D) C6H5 – C = CH – (CH2)2OH C6H5 – C – (CH2)3 – OH
| |
CH3 CH3
(1) HCl (1) LiAlH4 / Et 2O H O

 Y   Z, Identify X, Y and Z
3
8.16   X     
( 2) CH2OH ( 2) H2O
|
CH2OH
X Y Z
O O
|| || HO CH2OH
(A) O
C–OC2H5 O COC2H5
O
O
|| O
O COOH HO CH2OH
(B) C–OC2H5
O
O
O
|| O O CH2OH
(C) O CH2OH
C–OC2H5
O O
O HO CH2OH HO COOH
(D) CH2OH
O
258

8.17 P Q S T U
The final product U is
(A) (B) S S (C) (D)

R R

 Y + Z 
O3 OH
8.18 X 
Zn,H2O 
Compound X in the above reaction is
(A) (B)
(C) (D)
SECTION - II : MULTIPLE CORRECT ANSWER TYPE
1.PCl
8.19  
5
X    Y 2 
NH 2 OH.HCl
 Z
H SO 4
2. CH3MgBr (1eq)
X, Y, Z are :
(A) (B)
(C) (D)
259

20 Which of the following products is/are correctly mentioned in the following reactions.
(A) HCHO   HCOONa + CH3OD
NaOD
(B) HCDO   DCOONa + CH2DOH

NaOH
(C) HCDO   DCOOEt + DCH2ONa

NaOEt
(D) D2CO   DCOONa + CD3OD

NaOD
8.21 The correct statement/s about the following reaction sequence is / are
(P)
(Q)
(A) 'R' gives an aldol condensation reaction on heating with NaOH solution
(B) The compound 'Q' gives a yellow precipitate in acetone
(C) Step '4' is an aromatic nucleophilic substitution reaction
(D) The end product is a mixture of three compounds
8.22 Which statement is /are correct ?

(A) The rates of acid catalysed chlorination, bromination of acetone are same
(B) The rate of deuteration in presence of heavy water and the rate of acid catalysed halogenation are same
(C) Base catalysed haloform reaction involves formation of carbanion
(D) Acid catalysed halogenation of CH3COCH3 inovolves enol formation
8.23 Which one can be the product of the following reaction ?
1. NaOH, 
      
2. H3 O 
(A) A diacid (B) A monoacid (C) A diol (D) An alcohol
8.24 Which of these carbonyl compounds on reduction with Zn – Hg / HCl will give the same compound as product
(A) (B)
H–C=O
|
(C) H3C CH2 – C – CH3 (D)
|
H
8.25 Which one of the following compound will not show enolisation ?
(A) (B) (C) (D)
260

SECTION - III : ASSERTION AND REASON TYPE
8.26 Statement-1 : When chloral is heated with concentrated potassium hydroxide, it yields
[ CCl3– COO– & CCl3CH2OH ]
Statement-2 : In the cannizaro reaction hydride transfer is the slowest step.
(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
KOH
8.27 Statement-1 :  
 Expected major product from the above

reaction is .
Statement-2 : With increase in electrophilicity on > C = O group, rate of attack of nuecleophile increases.
8.28 Statement-1 : PhCOCOCOPh forms stable hydrate.

Statement-2 : The compound in the hydrate form has intramolecular H-bonding.
8.29 Statement-1 : When PhCHO is made to react in OD / D2O no D is incorporated into the CH2 of PhCH2OH,
PhCOO– mixture during Cannizaro's reaction.
Statement-2 : Intermolecular H transfer takes place in the rate determining step, with out getting free in
solution.
8.30 Statement-1 : When 1mole of benzaldehyde and 1 mole of cyclohexanone is treated with 1mol of semi
carbazide, cyclohexanone semicarbazone precipitates first and finally precipitate of semicarbazone of
benzaldehyde is formed
Statement-2 : Initial one is Kinetically controlled product and later one is thermodynamically controlled
product.
261

SECTION - IV : COMPREHENSION TYPE

Comprehension # 1
Aldehydes and Ketones reacts with NH2OH to form Aldoximes and Ketoximes respectively. Configuration of
these can be determined by Beckmann rearrangement as that group migrates which is anti w.r.t –OH.
R R
..
..
C N H C N  R' C  N  R 
H2
O  R'  C  N  R R'C  NH  R

R' OH R' OH2 | ||
OH O
It is interesting to note that the migration of group is completely Retentive and no loss of optical activity is
seen.
Me OH
O 2N C=N
8.31 H
Br
O O
|| ||
NH – C – Me C – NH – Me
(A) Br (B) Br
O2N O2N
O
O ||
|| C – NH – CH3
NH – C – Me
Br
(C) NO2 (D)
Br NO2
 H Br / KOH
8.32 CH3CHO + NH2OH  P Q 2  R (CH3NH2) (as only product)
Following is correct
(A) Oxime P is syn form of geometrical isomer (B) Oxime P is anti form
(C) Q is more basic than R (D) Q is H  C  NH  CH3

||
O
dil. H SO
8.33   2 4
Following is true about product

(A) It is also (+) laevorotatory (B) Both (+) (–) forms are obtained in equal amount
(C) It is having ‘S’ configuration for chiral carbon (D) It is having R configuration for chiral carbon.
262

Comprehension # 2
Intramolecular aldol condensation :
The aldol condensation also offer a convenient way to synthesize molecules with five and six membered ring.
This can be done by an intramolecular aldol condensation using a dialdehyde, a keto aldehyde or a diketone
as the substrate. The major product is formed by the attack of the enolate from the ketone side of the
molecule that adds to the aldehyde group. The reason the aldehyde group undergoes addition preferentially
may arise from the greater reactivity of aldehyde towards nucleophilic addition.
In reaction of this type five membered rings form far more readily than seven membered rings and six
membered rings are more favorable than four or eight membered rings when possible.
8.34 1–Ethylcyclopent–1–ene on reductive ozonolysis followed by aq. NaOH/ gives
(A) (B) (C) (D)
8.35 Which of the following compound on reaction with O3/Zn, H2O followed by aq. NaOH/ will form
(A) (B) (C) (D)
8.36 The true statement about the major product of in reaction with aq. NaOH
followed by heating is.

(A) It gives yellow ppt with I2/ O H (B) It gives silver mirror with Tollen’s reagent
(C) It shows stereoisomerism (D) It does not give yellow ppt with 2,4 DNP
Comprehension # 3
Observe the following reactions and its mechanistic steps and intermediate products.
Reaction-1 :
Reaction-2 : + + ACO 
263

8.37 The intermediate product similar to (IV) following in the reaction-(2) :
(A) (B)
(C) (D)
8.38 The leaving group of step (V) in reaction-2 :

(A) CH3COO (B) CO2 (C) PhCOO (D) Ph–CH=CH–COOH
8.39 If Ph–CH=O18 is used then O18 is traced in reaction -2 :
(A) Ph – C – O18 – H (B) CH3 – C – O18 – H

|| ||
O O
(C) Ph – CH  CH – C – O – H
18
(D) H – O – C – O18 – H
|| ||
O O
Comprehension # 4
In the 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 trihalo substituted ketone is formed hydroxide ion attacks
the carboxyl carbon because the trihalo methyl ion is the group more easily expelled from the tetrahedral
intermediate. The conversion of a methyl ketone to a carboxylic acid is called a haloform reaction because
one of the product is haloform (CHCI3) or CHI3 or CHBr3.

O H ( excess)
R – C – CH3   R – C – OH + CI3  R – C – O + CHI3
||  2 ( excess)
|| ||
O O
O
8.40 Which of the following compound show haloform reaction and racemisation in OD– / D2O.
O
Me Me
(A) CH3CH2OH (B) Ph
Et
(C) (D)
264

Et
|
(1)  2 / OH
Ph – C – C – C – CH3 
8.41   product is
|| | || ( 2 ) H
(3) 
O Me O
Me
|
(A) Ph – C – C – COOH (B) Ph – C – CH – Me
|| | || |
O Et O Et
(C) Ph – C – O – CH – Et (D) Ph – C – CH – OEt
|| | || |
O Me O Me
O
Ph
O
8.42   product is .
(1) NaOI
( 2 ) H ,
HOOC Ph
O
(A) O (B)
(C) (D)
SECTION - V : MATRIX - MATCH TYPE

8.43 Column-I Column-II
(A) (p) 1, 4-addition
(B) (q) Tautomerism
(C) CH3–CH=CH–CH = CH2 (r) AgNO3 / NH4OH
(D) (s) 2, 4 DNP test
(t) Br2 /H2O test
265

(A) (P) (Q) Product
(p) Formation of six member ring take place
(B) (P) (Q) (R) Product (q) Final product is ketone
(C) Product (r) Final product formed will give positive tollen's test
(D) Product (s) Final product will react with 2,4 DNP
(t) Final product have 5 membered ring.
(A) Product (p) Final product formed give positive tollen test
(B) Product (q) Final product give test with 2,4 DNP.
(C) Product (r) Final product react with NaHCO3 and liberated CO2 gas
(D) Ph–CH=O Product (s) Final product react with Na and liberated H2 gas.
(t) Final product lose CO2 on heating.
SECTION - VI : INTEGER TYPE

8.46 A compound (A) of molecular formula C14H10O2 is formed from C14H14O2 by oxidation Cr2O7–2. (A) upon
treatment with OH– gives (B). (B) on treatment with conc. H2SO4 and heat gives compound (C) of molecular
formula C28H20O4 (B) responds to NaHCO3 test and effervescence comes out. What should be the molecular
wt. of B ?
8.47 C8H6O2 on reaction with conc. NaOH undergoes a redox reaction to yield (A) which on treatment with
KMnO4 / H followed by NaOH / CaO gives an aromatic compound (X). Calculate the mol. mass of aromatic
compound (X).
8.48 Methyl cyclohexene on reductive ozonolysis followed by reaction with dil. NaOH gives [X] number of products.
A mixture of HCHO + PhCHO on treatment with conc. NaOH gives Y numberof products. 1, 2-Dimethyl
cyclohexene on reaction with metachloroperbenzoic acid gives [Z] number of products.
8.49 NH3 reacts with a gas fumes produced when methanol is passed through Cu tube at 573K. The compound
obtained is polycyclic. How many rings does it contain = [X]. The number of Nitrogen atoms it has = [Y] ?
HO
8.50 CH3—CH=O + PhCH2—CH=O   mixture of aldols
(z) total number of aldols including stereoisomers.
266

Aldehydes and Ketones: Topic

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 JEE (ADVANCED) - RRB

The compound 'C' is

(C) PhCO C Br2 (D)

8.2 The product/s of the following reaction is

8.3 Which step is not feasible in the following loop ?

(A) step - a (B) step - b (C) step - c (D) step - d

(A) CH3 CH(OH)COOH (B)

(C) CH3 CH = CH – COOH (D) CH3 CH C CH3

(C) PhCH2 CH(Br) COOH (D) PhCH = CH – COBr

8.7 The number of stereoisomeric products formed in the following reaction is

(A) 1 (B) 8 (C) 4 (D) 2

8.8 The end products of following reaction would be,

(A) + HCOONa (B) + HCOONa

(C) (D) + CH3OH

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

8.10 What will be the product of the following reaction

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

(A) 2 (B) 4 (C) 6 (D) 8

8.13 The final product (X) of the following reactions would be

(A) CH2=CH—CH=CH2 (B) CH3 – CH  CH — CH  CH2

(1) HCl (1) LiAlH4 / Et 2O H O

The final product U is

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

Compound X in the above reaction is

SECTION - II : MULTIPLE CORRECT ANSWER TYPE

(B) HCDO   DCOONa + CH2DOH

(C) HCDO   DCOOEt + DCH2ONa

(D) D2CO   DCOONa + CD3OD

8.22 Which statement is /are correct ?

8.23 Which one can be the product of the following reaction ?

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

SECTION - III : ASSERTION AND REASON TYPE

8.28 Statement-1 : PhCOCOCOPh forms stable hydrate.

SECTION - IV : COMPREHENSION TYPE

(C) Q is more basic than R (D) Q is H  C  NH  CH3

Following is true about product

8.34 1–Ethylcyclopent–1–ene on reductive ozonolysis followed by aq. NaOH/ gives

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

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

Reaction-2 : + + ACO 

8.38 The leaving group of step (V) in reaction-2 :

8.39 If Ph–CH=O18 is used then O18 is traced in reaction -2 :

(A) Ph – C – O18 – H (B) CH3 – C – O18 – H

SECTION - V : MATRIX - MATCH TYPE

(A) (p) 1, 4-addition

(B) (q) Tautomerism

(C) CH3–CH=CH–CH = CH2 (r) AgNO3 / NH4OH

(D) (s) 2, 4 DNP test

(t) Br2 /H2O test

(A) (P) (Q) Product

(p) Formation of six member ring take place

(B) (P) (Q) (R) Product (q) Final product is ketone

(t) Final product have 5 membered ring.

8.45 Column-I Column-II

(t) Final product lose CO2 on heating.

SECTION - VI : INTEGER TYPE

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