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Aldehydes and Ketones: Topic
Aldehydes and Ketones: Topic
TOPIC
ALDEHYDES AND KETONES
8
SECTION - I : STRAIGHT OBJECTIVE TYPE
– –
A B
C
OH H
8.1 PhCOCHBr2
OH
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
Br
EtOH, H |
CH2(Br)CH2CHO
a CH2 — CH2CH (OEt )2
H O, H
CH2=CHCHO 2 CH2=CHCH(OEt)2
c
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8.4 P
OH H3 O
Q
2Q 2
R
H SO
4
The product R is :
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)
HO
+
Ether 2
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8.9 In which of the following compounds O18 exchange can be observed on keeping it in H2O18
8.11 The possible number of stereoisomers of the product of following reaction would be :
Ph – CH = CH – CH – CHO
| NH2OH
CH 3
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8.12 Which of the following ketone racemises in aqueous solution containing some acidic or basic impurities.
(A) (B)
(C) (D)
(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
CH3
|
CH CH — C CH2
(C) | (D) CH3–CH=CH–CH=CH–CH3
CH3
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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
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
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8.17 P Q S T U
Y + Z
O3 OH
8.18 X
Zn,H2O
(A) (B)
(C) (D)
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)
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20 Which of the following products is/are correctly mentioned in the following reactions.
(A) HCHO HCOONa + CH3OD
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
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 ?
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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.
(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
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.
(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
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.
(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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..
..
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
dil. H SO
8.33 2 4
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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.
8.35 Which of the following compound on reaction with O3/Zn, H2O followed by aq. NaOH/ will form
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 :
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8.37 The intermediate product similar to (IV) following in the reaction-(2) :
(A) (B)
(C) (D)
(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)
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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)
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8.44 Column-I Column-II
(C) Product (r) Final product formed will give positive tollen's test
(D) Product (s) Final product will react with 2,4 DNP
(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.
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.
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