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Chapter 26

Aldehydes, Ketones and Carboxylic Acids

1. A liquid was mixed with ethanol and a drop of 6. Iodoform can be prepared from all except
concentrated H2SO4 was added. A compound with [AIEEE-2012]
a fruity smell was formed. The liquid was
[AIEEE-2009] (1) Isopropyl alcohol

(1) HCHO (2) CH3COCH3 (2) 3 – Methyl – 2 – butanone


(3) CH3COOH (4) CH3OH (3) Isobutyl alcohol
2. Which of the following on heating with aqueous (4) Ethyl methyl ketone
KOH, produces acetaldehyde? [AIEEE-2009] 7. The most suitable reagent for the conversion of
(1) CH3CH2Cl (2) CH2ClCH2Cl R – CH2 – OH o R – CHO is [JEE (Main)-2014]
(3) CH3CHCl2 (4) CH3COCl (1) KMnO4
3. In Cannizzaro reaction given below (2) K2Cr2O7
(3) CrO3
: OH
:

2PhCHO PhCH2OH + Ph CO 2 (4) PCC (Pyridinium Chlorochromate)


the slowest step is [AIEEE-2009] 8. In the reaction,
(1) The transfer of hydride to the carbonyl group
LiAlH PCl
Alc.KOH
(2) The abstraction of proton from the carboxylic CH3 COOH 
4
o A 
5
oB  o C,
group the product C is [JEE (Main)-2014]
(3) The deprotonation of PhCH2OH (1) Acetaldehyde (2) Acetylene
(4) The attack of : OH at the carboxyl group (3) Ethylene (4) Acetyl chloride
4. Ozonolysis of an organic compound ‘A’ produces 9. In the following sequence of reactions :
acetone and propionaldehyde in equimolar mixture.
KMnO SOCl H /Pd
Identify ‘A’ from the following compounds Toluene o
4
A 
2
o B 
2
BaSO
o C,
4
[AIEEE-2011]
the product C is [JEE (Main)-2015]
(1) 2 - Methyl - 2 - pentene
(1) C6H5COOH (2) C6H5CH3
(2) 2 - Methyl - 1 - pentene
(3) C6H5CH2OH (4) C6H5CHO
(3) 1 - Pentene
10. W hich of the following, upon treatment with
(4) 2 - Pentene
tert-BuONa followed by addition of bromine water,
5. In the given transformation, which of the following fails to decolourize the colour of bromine?
is the most appropriate reagent? [AIEEE-2012]
[JEE (Main)-2017]
Reagent
CH = CHCOCH3
O
O
HO
(1) (2)
CH = CHCH2CH3 Br Br

HO O C6H5
(1) Zn – Hg/HCI (2) Na, Liq. NH3
(3) (4)
Br Br
(3) NaBH4 (4) NH2NH2, OH

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11. The major product obtained in the following reaction 14. The major product of following reaction is
is [JEE (Main)-2017]
(1) AIH(i-Bu)2
R C N ? [JEE (Main)-2019]
O (2) H 2O
O
(1) RCH2NH2 (2) RCHO

DIBAL-H (3) RCONH2 (4) RCOOH


15. The correct match between Item I and Item II is
COOH Item I Item II
(A) Benzaldehyde (P) Mobile phase
CHO CHO
(B) Alumina (Q) Adsorbent
(1) (2)
COOH CHO (C) Acetonitrile (R) Adsorbate

OH OH [JEE (Main)-2019]
(1) (A) o (Q), (B) o (R), (C) o (P)

(3) CHO (4) CHO (2) (A) o (Q), (B) o (P), (C) o (R)

COOH CHO (3) (A) o (P), (B) o (R), (C) o (Q)

12. Phenol reacts with methyl chloroformate in the (4) (A) o (R), (B) o (Q), (C) o (P)
presence of NaOH to form product A. A reacts with 16. The major product formed in the following reaction is
Br2 to form product B. A and B are respectively
[JEE (Main)-2018] O CH3
O
OH Br OH
(1) and H 3C H+ dil. NaOH
OCH3 OCH3
O O [JEE (Main)-2019]
O OH
O O O O
(2) and
O O (1)
H3C
Br
OH O

O O O O (2)
H 3C H
(3) and O
O Br O OH

OH OH (3) H
and H3C
(4)
OCH3 OCH3
O O OH O
Br
13. The compounds A and B in the following reaction (4) H3C
are, respectively [JEE (Main)-2019]
17. The major product ‘X’ formed in the following
HCHO + HCI AgCN reaction is
A B
O O
|| ||
(1) A = Benzyl alcohol, B = Benzyl isocyanide CH2—C—OCH3
NaBH 4
(2) A = Benzyl chloride, B = Benzyl cyanide X
MeOH
(3) A = Benzyl chloride, B = Benzyl isocyanide
[JEE (Main)-2019]
(4) A = Benzyl alcohol, B = Benzyl cyanide

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OH OH O (1) OHC
CH2CH2OH CH2 C OCH3
(1) (2) OH

O O OH
CH2 C H CH2CH2OH (2) CH == CH — CHO
(3) (4)
COOH
18. Which dicarboxylic acid in presence of a dehydrating (3)
agent is least reactive to give an anhydride?
[JEE (Main)-2019]
CHO
COOH CO 2H
(4)
(1) (2)
COOH CO 2H OH
21. The major product obtained in the following reaction
O is
CH 2
CH2 COOH CH2 OH
CO2Et
(3) (4) NaOEt /'
o
CH2 COOH CH2 OH
O
CH2 O
O [JEE (Main)-2019]

19. The decreasing order of ease of alkaline hydrolysis O


for the following esters is (1)

COOC 2H5 CO2Et

I O
(2)
CO2Et
Cl COOC 2H5
O
(3)
II CO2Et

O2N COOC2H5 O
(4)
III
CO2Et
CH 3O COOC 2H5 22. The major porduct of the following reaction is
O
IV
CH3N NaBH 4
[JEE (Main)-2019]
[JEE (Main)-2019]
(1) III > II > IV > I (2) IV > II > III > I
OH
(3) II > III > I > IV (4) III > II > I > IV (1) CH3N
20. An aromatic compound ‘A’ having molecular OH
formula C7H6O2 on treating with aqueous ammonia (2) CH3N
and heating forms compound ‘B’. The compound
‘B’ on reaction with molecular bromine and O
potassium hydroxide provides compound ‘C’ having (3) CH3NH
molecular formula C6H7N. The structure ‘A’ is
OH
[JEE (Main)-2019] (4) CH3NH

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23. The major product of the following reaction is
CN O
COCH3
(i) KMnO4/KOH, '
(3)
(ii) H2SO 4(dil)
CH3
[JEE (Main)-2019]
OCH3
COCOOH
CH
(1) (4) CH2
HOOC

COOH
26. In the following reaction
(2)
HCI
HOOC Aldehyde + Alcohol Acetal

COOH Aldehyde Alcohol


HCHO tBuOH
(3)
OHC CH3CHO MeOH
The best combination is [JEE (Main)-2019]
COCH3
(1) HCHO and MeOH
(4)
HOOC (2) HCHO and tBuOH
24. The major product of the following reaction is: (3) CH3CHO and tBuOH
O (4) CH3CHO and MeOH
27. In the following reactions, products A and B are
OEt (i) Ni/H2

CN (ii) DIBAL–H O O
dil NaOH
[JEE (Main)-2019] H3C H [A]
H3C CH3
H +
H3O
NH [A] [B] [JEE (Main)-2019]
O '
(1) (2)
CHO O O
CH3 CH3
(1) A = CH3 ;B= CH3
OH N
HO
(3) (4)
NH2 O O
25. Which of the following compounds reacts with CH3 CH3
ethylmagnesium bromide and also decolourizes (2) A = CH3 ;B= CH3
bromine water solution? [JEE (Main)-2019] HO

O
O
OH
C CH3
H3C H H
(1) (3) A = ;B=
H3C H 3C
CH3 CH3

OH
O O
OH H 2C
H3C H H
(2) (4) A = ;B=
H3C H 3C
CH3 CH3

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28. The major product of the following reaction CHO
CN
(C) H3CO
+
O (ii) H3O CHO

O (D) HOH2C
[JEE (Main)-2019] [JEE (Main)-2019]

CHO CHO (1) (B), (C) (2) (B), (D)


(1) (2) (3) (B), (C), (D) (4) (C), (D)
O OH
31. The major product of the following reaction is
O CHO
H3C O
NH2
CH = NH CHO O
(3) (4) +
(i) NaNO2/H
OH O +
OH (ii) CrO3/H [JEE (Main)-2019]
(iii) H2SO4 (conc.),'

29. The increasing order of the reactivity of the following HO


with LiAlH4 is (1)
O
O
CH3 O
(A) C2H5 NH2 (2)
O
O O

(B) C2H5 OCH3 O

HO
O (3)
(C) C2H5 Cl
O
O O
(D) C2H5 CH3 O
O C2H5
(4)
O
[JEE (Main)-2019]
(1) (A) < (B) < (C) < (D) 32. The major product of the following reaction is
O
(2) (B) < (A) < (D) < (C) Br NaBH 4
MeOH, 25°C
(3) (A) < (B) < (D) < (C)

(4) (B) < (A) < (C) < (D)


[JEE (Main)-2019]
30. The aldehydes which will not form Grignard product
OH OH
with one equivalent Grignard reagent are Br OMe

CHO (1) (2)


(A)

CHO O OMe
(3) (4)
(B) HO2C

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33. An organic compound ‘X’ showing the following 36. The major product of the following reaction is
solubility profile is
LiAlH
water
insoluble
CH3CH CHCO2CH3 
4
o
X 5% HCl
insoluble [JEE (Main)-2019]
10% NaOH (1) CH3CH2CH2CH2OH
soluble
10% NaHCO3 (2) CH3CH2CH2CHO
insoluble

[JEE (Main)-2019] (3) CH3CH2CH2CO2CH3

(1) Benzamide (2) Oleic acid (4) CH3CH = CHCH2OH


(3) o-Toluidine (4) m-Cresol 37. The major product of the following reaction is
34. An organic compound neither reacts with neutral
ferric chloride solution nor with Fehling solution. It OH
however, reacts with Grignard reagent and gives CH2OH H 2 SO4 (cat.)
positive iodoform test. The compound is CHCl3
CO 2Et
[JEE (Main)-2019]

O [JEE (Main)-2019]
O
C2 H5 CH 3
(1) (2)
CH 3 H O
O OH
O
(1) (2)
O
OH O CO2Et
O
CH 3 CH 3
(3) (4)
C2 H5
OH
O
O OH

35. The major product obtained in the following reaction


(3) (4)
is OEt
COOH
O
CH3 O
NaOH
OHC '
38. In the following reaction

[JEE (Main)-2019] HCl


ZZZZ
carbonyl compound  MeOH YZZZ X
Z acetal

H3C CH3 Rate of the reaction is the highest for


(1) H (2) H [JEE (Main)-2019]
O O
CH2 CH3 (1) Acetone as substrate and methanol in excess

(2) Propanal as substrate and methanol in


CH3 CH3 stoichiometric amount

(3) Propanal as substrate and methanol in excess


(3) (4)
(4) Acetone as substrate and methanol in
O O stoichiometric amount

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39. Major products of the following reaction are : 42. The major product of the following reaction is
CHO (i) 50% NaOH
+ HCHO +
(ii) H3O
HO (1) CrO3
(2) SOCI2/'
[JEE (Main)-2019] HO (3) '
CH2OH [JEE (Main)-2019]
(1) HCOOH and
O O

CH2OH COOH (1) (2)


(2) and
CI HO
COOH O O
(3) CH3OH and
(3) (4)
(4) CH3OH and HCO2H
HO Cl
40. The major product ‘Y’ in the following reaction is:
43. The major product of the following reaction is
Ph CH3
NaOCI (i) SOCI2
X Y CH2CH3
O (ii) aniline
[JEE (Main)-2019] (i) alkaline KMnO4
+
(ii) H3O
Ph
NH2 N
O [JEE (Main)-2019]
O
(1) (2)
Ph CH2COOH COOH

(1) (2)
O NH2

HN Ph CH2CHO COCH3
(3) (4)
(3) (4)
O Ph

41. Compound A (C9H10O) shows positive iodoform 44. The major product of the following reaction is
test. Oxidation of A with KMnO 4 /KOH gives
acid B (C8H6O4). Anhydride of B is used for the O
preparation of phenolphthalein. Compound A is:
NaBH4
[JEE (Main)-2019] 
EtOH
o [JEE (Main)-2019]
CH3 CH3
(1) (2) O OH
CH3
(1) (2)
O
O CH3
O
OH
CH3 CH2 – C – H OH
(3) (4)
O (3) (4)
CH3
OEt
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45. What is the product of following reaction? 48. An unsaturated hydrocarbon X absorbs two
hydrogen molecules on catalytic hydrogenation, and
(i) NaBH also gives following reaction
Hex – 3 – ynal 
(ii)PBr
4
o?
3
(iii)Mg/ether
(iv) CO2 /H3O O [ Ag(NH ) ]
X 3
Zn/H O
o A 
3 2
o
2

[JEE (Main)-2020]
B(3-oxo-hexanedicarboxylic acid)
(1) COOH
X will be [JEE (Main)-2020]

(2) COOH

(3) COOH (1) (2)

(4)
COOH O
46. A solution of m-chloroaniline, m-chlorophenol and m-
chlorobenzoic acid in ethyl acetate was extracted (3) (4)
initially with a saturated solution of NaHCO3 to give
fraction A. The left over organic phase was extracted
49. Identify (A) in the following reaction sequence.
with dilute NaOH solution to give fraction B. The final
organic layer was labelled as fraction C. Fractions (A) 
3

(i) CH MgBr
o(B) o
3 2 O / Zn, H O

A, B and C, contain respectively : Gives
(ii) H , H2 O
(iii) Conc. H2SO4 / '
Positive
[JEE (Main)-2020] iodoform
test
(1) m-chloroaniline, m-chlorobenzoic acid and m- O
chlorophenol C
H
(2) m-chlorophenol, m-chlorobenzoic acid and m-
chloroaniline CH3

(3) m-chlorobenzoic acid, m-chlorophenol and m- H3C C O


chloroaniline CH3

(4) m-chlorobenzoic acid, m-chloroaniline and m- [JEE (Main)-2020]


chlorophenol
CH3
47. The most suitable reagent for the given conversion
is (1)
CONH2 CH 3 CH3
O
C ==O CH3
?
CH3
HO2 C
(2)
CN
O CH3

CONH2 CH3
COCH3

(3)
HOH2 C
O CH3
CN
[JEE (Main)-2020]
(1) LiAIH4 (2) NaBH4 (4)
(3) H2/Pd (4) B2H6 O CH3

Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
50. The major product (Y) in the following reaction is CHO
CH3 (iii)
HgSO4, H2SO4 OCH3
CH3–CH–C CH X
H2O

(i) C2H5MgBr, H2O O2N CHO


(ii) Conc. H2SO4/'
Y [JEE (Main)-2020] (iv) [JEE (Main)-2020]

CH3
(1) CH3–CH–C=CH–CH3 (1) (iii) < (iv) < (ii) < (i)

CH3 (2) (iii) < (i) < (iv) < (ii)


(3) (iii) < (iv) < (i) < (ii)
CH3
(4) (i) < (iii) < (iv) < (ii)
(2) CH3–C=C–CH3
53. The increasing order of the reactivity of the following
CH2CH3 compounds in nucleophilic addition reaction is
CH2 Propanal, Benzaldehyde, Propanone, Butanone
(3) H3C–C–CH–CH3 [JEE (Main)-2020]
C2H5 (1) Propanal < Propanone < Butanone <
CH3 Benzaldehyde
(2) Benzaldehyde < Propanal < Propanone <
(4) CH3–CH–C=CH2
Butanone
CH2CH3
(3) Benzaldehyde < Butanone < Propanone <
51. In the following reaction A is Propanal
H O (4) Butanone < Propanone < Benzaldehyde <
Propanal
(i) Br2, hQ
54. The compound A in the following reactions is
(ii) KOH (alc.)
A (i) CH MgBr/H O
(iii) O3 A 
3 2
o
(ii) Conc. H2SO 4 / '
(iv) (CH3)2S
(i) O
(v) NaOH (aq) + ' B o
3
C D
(ii) Zn/H2O
[JEE (Main)-2020]
(i) Conc. KOH
C  o COO K + + CH2OH
(ii) '

(1) (2) CH3 O


I II
Ba(OH)2
D  o H3 C  C CH  C  CH3
'

[JEE (Main)-2020]
O
(3) (4) II
(1)
C6H5  C  CH2 CH3

52. The increasing order of the following compounds O


towards HCN addition is (2) II
C6H5  C  CH3
H3CO CHO
O
(i) II
(3)
C6H5  CH2  C  CH3
CHO O
II CH 3
(ii) (4) C6 H5  C  CH
NO2 CH 3

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55. An organic compound (A) (molecular formula 58. The correct match between Item-I (starting material)
C6H12O2) was hydrolysed with dil. H2SO4 to give a and Item-II (reagent) for the preparation of
carboxylic acid (B) and an alcohol (C). ‘C’ gives benzaldehyde is
white turbidity immediately when treated with Item-I Item-II
anhydrous ZnCl 2 and conc. HCl. The organic
(I) Benzene (P) HCl and SnCl2,
compound (A) is [JEE (Main)-2020]
H3O+
O O (II) Benzonitrile (Q) H2, Pd-BaSO4, S
(1) (2) O and quinoline
O
(III) Benzoyl Chloride (R) CO, HCl and AlCl3
O O [JEE (Main)-2020]
(3) (4) (1) (I) - (R), (II) - (P) and (III) - (Q)
O O
(2) (I) - (P), (II) - (Q) and (III) - (R)
56. [P] on treatment with Br2/FeBr3 in CCl4 produced
a single isomer C8H7O2Br while heating [P] with (3) (I) - (Q), (II) - (R) and (III) - (P)
sodalime gave toluene. The compound [P] is (4) (I) - (R), (II) - (Q) and (III) - (P)
[JEE (Main)-2020] 59. Consider the following reactions[JEE (Main)-2020]

COOH COOH
(i) CH MgBr
Cu
A 
3
 o B  o 2  methyl  2  butene
CH3 573 K
(ii) H3O

(1) (2) The mass percentage of carbon in A is ______ .


CH3 [JEE (Main)-2020]

COOH CH2COOH 60. The number of chiral centres present in [B] is


_____.

(3) (4) (i) C2 H5 MgBr


CH C N +
[A]
(ii) H3 O
CH3
CH3
57. Consider the following reactions (i) CH3 MgBr
[B] [JEE (Main)-2020]
ozonolysis (ii) H 2O
' A ' o 'B ' 'C '
(C7H14 ) 61. An organic compound [A], molecular formula
C10H20O2 was hydrolyzed with dilute sulphuric acid
(I2 + NaOH)
‘B’ yellow ppt to give a carboxylic acid [B] and an alcohol [C].
' Oxidation of [C] with CrO3 – H2SO4 produced [B].
Which of the following structures are not possible for
(Ag2O) [A]? [JEE (Main)-2020]
silver mirror
'
CH3
(I2 + NaOH) |
no yellow ppt (1) CH3  CH2  CH  OCOCH2CH  CH2CH3
‘C’ ' |
gives white CH3
LiAlH4 Anhydrous ZnCl 2 turbidity
‘D’ & Conc. HCl within
5 minutes
CH3
‘A’ is [JEE (Main)-2020] |
(2) CH3  CH2  CH  COOCH2  CH  CH2CH3
|
(1) (2)
CH3

(3) (CH3)3C – COOCH2C(CH3)3


(3) (4) (4) CH3(CH2)2CH2COOCH2(CH2)2CH2CH3

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62. Which of the following compound gives pink colour 65. Which one of the following reactions will not form
on reaction with phthalic anhydride in conc. H2SO4 acetaldehyde? [JEE (Main)-2021]
followed by treatment with NaOH? CrO 3 H2 SO 4
(1) CH3 CH2 OH  o
[JEE (Main)-2021]
Pd(II)/Cu(II)
(2) CH2 CH2  O2 HO
o
CH 3 2

(1) Cu
HO (3) CH3CH2OH
573 K
o
(i) DIBAL-H
(4) CH3CN 
(ii) H O
o
HO CH 3 2

(2) 66. The major product of the following chemical


reaction is:
HO CH3
1) H3 O  ,'
2) SOCl2
CH3 CH2 CN  
3) Pd/BaSO 4 ,H2
o?
H 3C CH3
(3) [JEE (Main)-2021]
(1) CH3CH2CH3 (2) CH3CH2CH2OH
HO OH
(3) CH3CH2CHO (4) (CH3CH2CO)2O
67. Compound(s) which will liberate carbon dioxide
CH3
with sodium bicarbonate solution is/are :
(4)
OH NH2

63. Which of the following reagent is used for the


following reaction?
A=
?
CH3 CH2CH3  o CH3 CH2CHO
NH2 NH2
[JEE (Main)-2021] OH
(1) Copper at high temperature and pressure
COOH
(2) Manganese acetate
(3) Molybdenum oxide
(4) Potassium permanganate B=

?
64. OH
O
NO2 NO2

Which of the following reagent is suitable for the


C=
preparation of the product in the above reaction?
[JEE (Main)-2021]
(1) Red P + Cl2 NO2
(2) Ni/H2
[JEE (Main)-2021]
(3) NaBH4
(1) B only (2) C only
–† (3) A and B only (4) B and C only
(4) NH2–NH2 /C2H5 ONa

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68. The correct sequence of reagents used in the 73. Identify A in the following chemical reaction.
preparation of 4-bromo-2-nitroethyl benzene from
benzene is: [JEE (Main)-2021] CHO
(i) HCHO, NaOH
(1) CH3COCl/AlCl3, Zn-Hg/HCl, Br2/AlBr3, HNO3/ A
(ii) CH3CH2 Br, NaH, DMF
CH3O (iii) HI, '
H2SO4
(2) HNO 3 /H 2 SO 4 , Br 2 /AlCl 3 ,CH 3 COCl/AlCl 3 , [JEE (Main)-2021]
Zn-Hg/HCl
(3) CH 3 COCl/AlCl 3 , Br 2 /AlBr 3 , HNO 3 /H 2 SO 4 , CH2I
Zn/HCl (1)
HO
(4) Br 2 /AlBr 3 , CH 3 COCl/AlCl 3 , HNO 3 /H 2 SO 4 ,
Zn/HCl
CH2OH
69. The major product of the following reaction is : (2)
HO
H /CO
CH3CH2CH CH2 
2
Rh catalyst
o
O
[JEE (Main)-2021]
C — OCH2CH3
(1) CH3CH2 C CH2 (3)
CHO HO

(2) CH3CH2CH2CHO
CH2 OH
(3) CH3CH2CH2CH2CHO
(4)
(4) CH3CH2CH == CH — CHO CH3O
70. The number of compound/s given below which
contain/s —COOH group is ____ . (Integer answer) 74. Identify A in the given chemical reaction.

[JEE (Main)-2021] CH2CH2 CHO


NaOH
(A) Sulphanilic acid (B) Picric acid C2H5 OH, H 2O
A (Major Product)
CH2CH2 CHO '
(C) Aspirin (D) Ascorbic Acid

A Hydrolysis B [JEE (Main)-2021]


71. (C4 H8O)
(C4 H8Cl2 ) 373K
CHO
B reacts with Hydroxyl amine but does not give (1)
Tollen’s test. Identify A and B.
[JEE (Main)-2021]
CH2CH2 COOH
(1) 2,2-Dichlorobutane and Butanal
(2)
(2) 1,1-Dichlorobutane and Butanal CH2CH2 CH2OH
(3) 1,1-Dichlorobutane and 2-Butanone
(4) 2,2-Dichlorobutane and Butan-2-one O
(3)
72. 2,4-DNP test can be used to identify O
[JEE (Main)-2021]
(1) Aldehyde O
(2) Amine C—H
(3) Ether
(4)
(4) Halogens

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O (i) C6H5MgBr Ether
O CN (1.0 equivalent), dry
X
i) DIBAL-H, Toluene, –78°C 78. (ii) H3O
+

75. + “P” Major Product


ii) H 3O
(Major Product)
OCH3
The product “P” in the above reaction is : The structure of X is: [JEE (Main)-2021]
[JEE (Main)-2021] O

CHO C6 H5 NH2
(1) (1) (2)
C6 H5

C6H 5
COOH O
(2)
NH2 C6 H5
(3) (4)
OH

OCH3 OCH3
(3) CHO
79. Mesityl oxide is a common name of
[JEE (Main)-2021]
O (1) 3-Methyl cyclohexane carbaldehyde
O–C–H
(2) 2, 4-Dimethyl pentan-3-one
(4) (3) 2-Methyl cyclohexanone
(4) 4-Methyl pent-3-en-2-one
O O Ethylene Glycol A
76. An unsaturated hydrocarbon X on ozonolysis gives (Major Product)
80.
A. Compound A when warmed with ammonical OC2H 5 H+
silver nitrate forms a bright silver mirror along the
The product “A” in the above reaction is
sides of the test tube. The unsaturated
[JEE (Main)-2021]
hydrocarbon X is: [JEE (Main)-2021]
CH 3 OH
(1) CH3 C = O
O
(1) OH
(2) CH3 C = C CH3 OC2 H5
CH3 CH3

(3) HC { C – CH2 – CH3


O
(4) CH3 – C { C – CH3 (2) O O

OH
CH 3 COO H
“A”
77.
O
OCH3 OCH3 (3) O O

OC 2H5
In the above reaction, the reagent “A” is:
[JEE (Main)-2021] O
(1) HCl, Zn – Hg
OC2H 5
(2) Alkaline KMnO4, H+ (4)
(3) LiAlH4
OH
(4) NaBH4, H3O+

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CH3 CH2NH 2 CONH 2
(1) (2)
Alkaline KMnO 4
81. "X"
H+

OCH 3 H
CH2NO2 C N OH
Considering the above chemical reaction, identify (3) (4)
the product “X” : [JEE (Main)-2021]

COOH CH 3 O

(1) X – (2) X – dil. NaOH H+, Heat


84. 2 “X” “Y”

OCH3 OH
Consider the above reaction, the product ‘X’ and ‘Y’
respectively are [JEE (Main)-2021]
CH2OH CHO
OH O
(3) X – (4) X –
(1) ,
OCH3 OCH 3 O

82. Reaction of Grignard reagent, C 2H 5MgBr with O O


C8H8O followed by hydrolysis gives compound "A"
which reacts instantly with Lucas reagent to give (2)
OH ,
compound B, C10H13Cl. [JEE (Main)-2021]

CH3 CH3 O O
Cl
CH 3
(1) (2) (3) ,
Cl OH

Cl O O
Cl CH3
(4) ,
OH
CH 3 CH3
(3) (4)
85. In Tollen’s test for aldehyde, the overall number of
electron(s) transferred to the Tollen’s reagent
formula [Ag(NH3)2]+ per aldehyde group to form
silver mirror is_______. (Round off to the Nearest
C N Integer). [JEE (Main)-2021]
86. The number of nitrogen atoms in a semicarbazone
H 2O molecule of acetone is _______.[JEE (Main)-2021]
83. +
“A”
H (Major Product)

COOH 87.
H2O
H,'
+

Which among the above compound/s does/do not


Consider the above chemical reaction and identify form Silver mirror when treated with Tollen’s reagent?
product “A” [JEE (Main)-2021] [JEE (Main)-2021]

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(1) (I), (III) and (IV) only (2) (III) and (IV) only 90. Which one of the following compounds will provide
(3) Only (IV) (4) Only (II) a tertiary butyl alcohol on reaction with excess of
88. The major product (P) in the following reaction is CH3MgBr followed by hydrolysis?

O [JEE (Main)-2021]
CHO
KOH (alc.)
+
P
(ii) H , '
(major product)
O
O
[JEE (Main)-2021]
(1)
O
O
(1)
O

CHO O CH 3
(2)
(2) O
O

O OCH 2CH3

OHC NC
(3) C

CH
(3)

O
CH 3
(4)

OH
(4)

O O (i) C 2H5MgBr, dry ether


(ii) H 2O, HCl P
91. (Major product)
O
O O
89. (A) (B) Consider the above reaction, the major product ‘P’
R Cl R O R
is [JEE (Main)-2021]
O
O
H OH
(C) R (D) R N OH
R O H (1) (2) Cl
The correct order of their reactivity towards
hydrolysis at room temperature is
[JEE (Main)-2021]
(1) (A) > (B) > (C) > (D) OH
OH
(2) (A) > (C) > (B) > (D)
(3) (4)
(3) (D) > (A) > (B) > (C) Cl
(4) (D) > (B) > (A) > (C)
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O OEt H2C OEt
CH3CHO (i) I 2/NaOH, Filter
92. ‘P’ ‘X’ (3) EtO ,
NaOH (Major Product) (ii) Filtrate + HCI
OEt OEt
Consider the given reaction, the product ‘X’ is
O tBu
[JEE (Main)-2021]
(4) EtO CHO EtO ,
,
O OH O O OH

(1) (2) 95. A reaction of benzonitrile with one equivalent


CH 3 MgBr followed by hydrolysis produces a
yellow liquid “P”. The compound “P” will give
O O OH positive ______. [JEE (Main)-2021]
(1) Tollen’s test (2) Schiff’s test
(3) OH (4) CHO
(3) Ninhydrin’s test (4) Iodoform test

(i) DIBAL H
96. R  CN (ii) H O
oR  Y
2
93. O
Consider the above reaction and identify “Y”.
O [JEE (Main)-2021]
(1) –CH2NH
O
(2) –CHO
Maleic anhydride
(3) –COOH
Maleic anhydride can be prepared by : (4) –CONH2
[JEE (Main)-2021] 97. The major products formed in the following reaction
(1) Treating cis-but-2-enedioic acid with alcohol sequence A and B are [JEE (Main)-2021]
and acid O

(2) Heating cis-but-2-enedioic acid CH3 Br 2


A+ B
KOH
(3) Treating trans-but-2-enedioic acid with alcohol
and acid
O
(4) Heating trans-but-2-enedioic acid
(1) A = C , B = CHBr 3
EtOH excess
t
BuO K
– + OK
"A" "B"
94. Br CHO dry HCl gas (major (major
product) product)
Br O HO O
[where Et Ÿ –C2H5 tBu
Ÿ (CH3)3C – ] (2) A = C – CH 3, B= C – CH3
Consider the above reaction sequence, Product “A” Br HO
and Product “B” formed respectively are :
[JEE (Main)-2021] O
(3) A = C – CBr 3, B= CHO
OEt OEt
t
(1) Br , BuO
OEt OEt O
(4) A = C – CH2 – Br ,
OEt H2 C OEt O
Br
(2) Br , B= C – CH2 – OH
OEt OEt Br

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98. The major product formed in the following reaction OH
O
is [JEE (Main)-2021] 100.
“X” CN LiAlH4 “Y”
H HCN, H O +
2 H H3O (Major Product)

Consider the given reaction, Identify “X” and “Y”


[JEE (Main)-2021]

COCl OH
(1)
N NH2 NH2
H (1) X – NaOH Y- H

Cl CO2Me
(2) OH
N NH2
H
NH2
(2) X – HNO 3 Y- H

(3)
N NH2˜HCl
H OH
NH 2
(3)
X – NaOH Y- H
(4)
N NH2˜HCl
H˜HCl
OH
99. Match List-I with List-II. NH2
(4) X – HNO 3 Y- H
List-I List-II
(Chemical reaction) (Reagent used)
(a) CH3COOCH2CH3 (i) CH3MgBr/H3O+ 101. In the following sequence of reactions, the final
o CH3CH2OH (1 equivalent) product D is : [JEE (Main)-2021]

(b) CH3COOCH3 (ii) H2SO4/H2O


OH
o CH3CHO
Br CH3 H2/Pd-C
CH 3–C{C–H+NaNH2 A B C
(c) CH3C { N (iii) DIBAL-H/H2O
CrO3
o CH3CHO
D
(d) CH3 C { N (iv) SnCl2, HCl/H2O
O
o CH 3 CH3 O
||
(1) CH3  CH2  CH2  CH2  CH2  C  CH3
Choose the most appropriate match.
[JEE (Main)-2021] (2) H3C – CH = CH – CH(OH) – CH2 – CH2 – CH3

(1) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i) (3) CH3 – CH = CH – CH2 – CH2 – CH2 – COOH

(2) (a)-(iii), (b)-(ii), (c)-(i), (d)-(iv)


O
(3) (a)-(ii), (b)-(iv), (c)-(iii), (d)-(i) ||
(4) H3 C  CH2  CH2  CH2  CH2  C  H
(4) (a)-(iv), (b)-(ii), (c)-(iii), (d)-(i)

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102. The structure of the starting compound P used in
CH3
the reaction given below is:
NC CH3
1. NaOCl OH
P 2. H3O
+ (1)
O
CH3
[JEE (Main)-2021]
O CH3
O
CH3
(1) (2) (2) CH3
O

CH 3

H O
(3) (4) CH3

O CH3
NC
103. Which one of the following reactions will not yield (3)
propionic acid? [JEE (Main)-2021]
CH3
(1) CH3CH2CH3 + KMnO4(Heat), OH–/H3O+
(2) CH3CH2COCH3 + OI–/H3O+ O CH3
(3) CH3CH2CH2Br + Mg,CO2 dry ether/H3O+
CH3
(4) CH3CH2CCl3 + OH–/H3O+ (4) CH3
104. Given below are two statements :
CH 3
Statement I : Ethyl pent-4-yn-oate on reaction
with CH3MgBr gives a 3°-alcohol. 106. The structure of product C, formed by the following
Statement II : In this reaction one mole of ethyl sequence of reactions is :
pent-4-yn-oate utilizes two moles
of CH3MgBr.
Benzene KCN
CH3COOH + SOCl 2 A B C
In the light of the above statements, choose the AlCl3 –
OH
most appropriate answer from the options given
[JEE (Main)-2021]
below: [JEE (Main)-2021]
(1) Both Statement I and Statement II are true O

(2) Statement I is false but Statement II is true CH3


(1)
(3) Statement I is true but Statement II is false CN

(4) Both Statement I and Statement II are false H COOH


C
105. Which one of the following is the major product of CH 3
the given reaction? (2)

[JEE (Main)-2021]
CH2 – CH2 CN
(3)
CH3

NC O (i) 2CH 3 MgBr


+
NC OH
(ii) H 3O
(iii) H 2SO 4, heat CH3
(4)
CH3

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107. For the reaction given below : 111. Given below are two statements:
CHO Statement I : The nucleophilic addition of sodium
hydrogen sulphite to an aldehyde or a ketone
1. NaOH, ' involves proton transfer to form a stable ion.
Product
2. H 3O
+ Statement II : The nucleophilic addition of
hydrogen cyanide to an aldehyde or a ketone
CH2OH yields amine as final product.
[JEE (Main)-2021]
The compound which is not formed as a product in
In the light of the above statements, choose the
the reaction is a : [JEE (Main)-2021]
most appropriate answer from the options given
(1) Dicarboxylic acid below:
(2) Monocarboxylic acid (1) Statement I is true but Statement II is false
(2) Statement I is false but Statement II is true
(3) Compound with both alcohol and acid
(3) Both Statement I and Statement II are true
functional groups
(4) Both Statement I and Statement II are false
(4) Diol 112. ________ grams of 3-Hydroxy propanal (MW = 74)
108. Experimentally reducing a functional group cannot must be dehydrated to produce 7.8 g of acrolein (MW
be done by which one of the following reagents ? = 56) (C3H4O) if the percentage yield is 64.
(Round off to the Nearest Integer).
[JEE (Main)-2021]
[Given : Atomic masses : C : 12.0 u, H : 1.0 u, O :
(1) Pd-C/H2 (2) Pt-C/H2 16.0 u] [JEE (Main)-2021]
(3) Zn/H2O (4) Na/H2 113. What is ‘X’ in the given reaction?
109. In the following sequence of reactions a compound CH2OH
210°C
A, (molecular formula C6H12O2) with a straight + oxalic acid X
chain structure gives a C4 carboxylic acid. A is : CH2OH d uct)
(major prod

LiAlH4 Oxidation [JEE (Main)-2021]


A +
B C4-carboxylic acid
H 3O CHO CH2
(1) (2)
CHO CH2
[JEE (Main)-2021]
(1) CH3 – CH2 – COO – CH2 – CH2 – CH3 CH – OH CH2OH
(3) (4)
(2) CH3 – CH2 – CH2 – O – CH = CH – CH2 – OH CH2 CHO

(3) CH3 – CH2 – CH2 – COO – CH2 = CH3 114. Which one of the following compounds will give
orange precipitate when treated with 2,
OH 4-dinitrophenyl hydrazine? [JEE (Main)-2021]
O
(4) CH3 – CH 2 – CH – CH2 – O – CH = CH 2
OCH2CH3
110. In the following sequence of reactions, (1)

+
H /H2O KIO O
C3 H6 A B+C
dil KOH C OH
The compounds B and C respectively are : (2)
[JEE (Main)-2021] OH
OH
(1) Cl3COOK, HCOOH (3)
OCH 2CH3
(2) CHl3, CH3COOK
O
(3) Cl3COOK, CH3l O

(4) CH3I, HCOOK (4)

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115. Two statements are given below:
Statement I: The melting point of monocarboxylic
acid with even number of carbon atoms is higher than
that of with odd number of carbon atoms acid
immediately below and above it in the series. (1) (2)
Statement II: The solubility of monocarboxylic acids
in water decreases with increase in molar mass.
Choose the most appropriate option:
[JEE (Main)-2022]
(1) Both Statement I and Statement II are
correct.
(2) Both Statement I and Statement II are
incorrect.
(3) (4)
(3) Statement I is correct but Statement II is
incorrect.
(4) Statement I is incorrect but Statement II is
correct.
118. Number of electrophilic centres in the given
116. Which of the following is an example of conjugated
compound is ______.
diketone?
[JEE (Main)-2022]

(1)

(2)
[JEE (Main)-2022]
119. Hex-4-ene-2-ol on treatment with PCC gives ‘A’ on
(3)
reaction with sodium hypoiodite gives ‘B’, which on
further heating with soda lime gives ‘C’. The
compound ‘C’ is
(4) [JEE (Main)-2022]
(1) 2-pentene (2) Proponaldehyde
(3) 2-butene (4) 4-methylpent-2-ene
120. The conversion of propan-1-ol to n-butylamine
involves the sequential addition of reagents. The
correct sequential order of reagents is
117. [JEE (Main)-2022]
(1) (i) SOCl2 (ii) KCN (iii) H2/Ni, Na(Hg)/C2H5OH
(2) (i) HCl (ii) H2/Ni, Na(Hg)/C2H5OH

The major product of the above reactions is : (3) (i) SOCl2 (ii) KCN (iii) CH3NH2

[JEE (Main)-2022] (4) (i) HCl (ii) CH3NH2

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121. In the given reaction

OH 124.

(i) 2 Mg, THF C


2A Consider the above reaction sequence and identify
(ii) Methyl benzoate
+
(iii) H2O/H the product B.
[JEE (Main)-2022]

‘A’ can be
[JEE (Main)-2022]
(1) Benzyl bromide (2) Bromo benzene (1)
(3) Cyclohexyl bromide (4) Methyl bromide
122. Which of the following conditions or reaction
sequence will NOT give acetophenone as the
major product?
[JEE (Main)-2022]
(2)

(1)

(3)

(2)

(4)
(3)

125. Oxidation of toluene to benzaldehyde can be easily


carried out with which of the following reagents?
(4) [JEE (Main)-2022]
(1) CrO3/acetic acid, H3O+
123. W hich of the following ketone will NOT give (2) CrO3/acetic anhydride, H3O+
enamine on treatment with secondary amines? (3) KMnO4/HCl, H3O+
[where t-Bu is –C(CH3)3] (4) CO/HCl, anhydrous AlCl3
[JEE (Main)-2022] 126. The reagent, from the following, which converts
benzoic acid to benzaldehyde in one step is

(1) (2)

[JEE (Main)-2022]
(1) LiAlH4 (2) KMnO4
(3) (4)
(3) MnO (4) NaBH4

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127. The final product ‘A’ in the following reaction 129. Decarboxylation of all six possible forms of
sequence diaminobenzoic acid C6H3(NH2)2COOH yields three
products A, B and C. Three acids give a product
‘A’, two acids give a product ‘B’ and one acid gives
a product ‘C’. The melting point of product ‘C’ is
[JEE (Main)-2022] [JEE (Main)-2022]
(1) 63ºC (2) 90ºC
(1) (3) 104ºC (4) 142ºC
130. The correct structure of product ‘A’ formed in the
following reaction,
(2)

(Ph is - C6H5) is
(3) [JEE (Main)-2022]

(1) (2)
(4)

128. W hich of the following reactions will yield


(3) (4)
benzaldehyde as a product?
131. The correct IUPAC name of the following
compound is:
(A)

[JEE (Main)-2022]
(1) 4-methyl-2-nitro-5-oxohept-3-enal
(B) (2) 4-methyl-5-oxo-2-nitrohept-3-enal
(3) 4-methyl-6-nitro-3-oxohept-4-enal
(4) 6-formyl-4-methyl-2-nitrohex-3-enal
132. Isobutyraldehyde on reaction with formaldehyde
and K2CO3 gives compound ‘A’. Compound ‘A’
(C)
reacts with KCN and yields compound ‘B’, which
on hydrolysis gives a stable compound ‘C’. The
compound ‘C’ is [JEE (Main)-2022]

(D) (1)

[JEE (Main)-2022]
(1) (B) and (C) (2) (C) and (D)
(2)
(3) (A) and (D) (4) (A) and (C)

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136. In the given reaction,

(3)

The number of S electrons present in the product


(4) ‘P’ is_____. [JEE (Main)-2022]
137. Which one of the following reactions does not
represent correct combination of substrate and
product under the given conditions?
133. [JEE (Main)-2022]

In the given conversion the compound A is: (1)


[JEE (Main)-2022]

(1) (2) (2)

(3) (4) (3)

134. Given below are two statements:


Statement I: The esterification of carboxylic acid (4)
with an alcohol is a nucleophilic acyl substitution.
Statement II: Electron withdrawing groups in the 138. In the given reaction,
carboxylic acid will increase the rate of esterification
reaction.
Choose the most appropriate option :
[JEE (Main)-2022]
(1) Both Statement I and Statement II are
correct.
(2) Both Statement I and Statement II are (where Et is –C2H5)
incorrect.
The number of chiral carbon(s) in product A is
(3) Statement I is correct but Statement II is
______.
incorrect.
(4) Statement I is incorrect but Statement II is [JEE (Main)-2022]
correct. 139. W hat is the major product of the following
reaction?
135. C H O 
Zymase NaOI
o A  o B  CHI3
6 12 6 '
The number of carbon atoms present in the
product B is ______.
[JEE (Main)-2022]

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[JEE (Main)-2022]

(1) (2)
(3)

(3) (4)

140.
(4)

142. Which reactant will give the following alcohol on


The correct structure of C is reaction with one mole of phenyl magnesium
[JEE (Main)-2022] bromide (PhMgBr) followed by acidic hydrolysis?
(1)

(2)

[JEE (Main)-2022]
(3) (1) CH3 – C { N (2) Ph – C { N

(4) (3) (4)

141. The products formed in the following reaction, A


and B are

143.

Consider the above reaction and predict the major


product.
[JEE (Main)-2022]
[JEE (Main)-2022]
(1)

(1) (2)

(3)

(2)
(4)

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144. The structure of A in the given reaction is: [JEE (Main)-2022]
(1) (A) - (IV), (B) - (III), (C) - (II), (D) - (I)
(2) (A) - (I), (B) - (II), (C) - (III), (D) - (IV)
(3) (A) - (II), (B) - (III), (C) - (IV), (D) - (I)
(4) (A) - (III), (B) - (II), (C) - (I), (D) - (IV)
[JEE (Main)-2022] 146. The spin only magnetic moment of the complex
present in Fehling’s reagent is_____ B.M. (Nearest
integer).
[JEE (Main)-2022]
(1)

147.

(2) In the above reaction, 5 g of toluene is converted


into benzaldehyde with 92% yield. The amount of
benzaldehyde produced is______ × 10 –2 g.
(Nearest integer).
(3) [JEE (Main)-2022]

148.
(4)

Find out the major product for the above reaction.


145. Match List-I with List-II [JEE (Main)-2022]
List-I List-II

o
(A) (I) Gatterman Koch (1)
o

reaction
I
(B) (II) Etard reaction
CO2 H
(2)
I
(C) (III) Stephen

reaction
o
(3)
o
(D) (IV) Rosenmund

reaction
Choose the correct answer from the options given o
(4)
below: o

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(1) H

149.

H
(2)
Consider the above reaction sequence, the product
‘C’ is
[JEE (Main)-2022]
(3) H

H
(1) (2) (4)

152. The number of stereoisomers formed in a reaction


of (±) Ph (C = O) C (OH) (CN) Ph with HCN
is_____.
[where Ph is –C6H5] [JEE (Main)-2022]
(3) (4)
153. 4-Bromophenyl acetic acid.

150. Consider the following reaction sequence :

In the above reaction ‘A’ is [JEE (Main)-2022]

The product ‘B’ is : (1)


[JEE (Main)-2022]

(1)

(2) (2)

(3)

(3)
(4)

151. Correct structure of J-methylcyclohexane


carbaldehyde is [JEE (Main)-2022]
(4)

‰‰‰

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Chapter 26
Aldehydes, Ketones and Carboxylic Acids

1. Answer (3) LiAlH4


CH3COOH CH3CH2OH 'A'

H
Liquid + ethanol o Fruity smell compound PCl5

p p CH3CH2Cl 'B'
Carboxylic acid Must be ester Alc. KOH

H
CH3COOH + C2H5OH o CH3COOC2H5 CH2 = CH2 'C'
2. Answer (3) 9. Answer (4)
OH
aq. KOH CH3 COOH COCl CHO
CH3CHCl2 CH3CH
gem-dihalide OH KMnO4 SOCl2 H2/Pd
unstable BaSO4
–H2O (A) (B) (C)

CH3CHO 10. Answer (3)


3. Answer (1) CH3
In Cannizzaro reaction, the transfer of hydride to + –
Na O C CH3
the carbonyl group is the rate determining step.
O
4. Answer (1) CH3
Br
CH3 H
O3 CH3
CH3 C C CH2 CH3
Zn/H2O
O O C CH3
CH3 O
CH3
CH3 C O + CH3 CH2 C H (Product)
acetone
5. Answer (4) The above product does not have any C = C or
6. Answer (3) C { C bond, so, it will not give Br2-water test.
11. Answer (4)
7. Answer (4) DIBAL — H reduces esters and carboxylic acids
PCC is mild oxidising agent, it will convert into aldehydes
R  CH2  OH oR  CHO O O OH H O

8. Answer (3)
DIBAL-H
Ethylene

COOH CHO

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12. Answer (3) 16. Answer (4)
O
OH3 O– O – C – O – CH3
O O O





OH– Cl – C – O – CH3 –
C – CH3 OH – C – CH2



Br 2
CH3 – C – H
O O OH




O – C – O – CH3 C – CH2 – CH – CH3

Br
Hence, option (3) is correct. 17. Answer (2)
13. Answer (3) NaBH4 selectively reduces the ketone, it does not
CH2 – Cl affect alkene and ester.

+ HCHO + HCl
O
O
Benzyl chloride CH 2 – C – OCH 3
NaBH 4
AgCN MeOH

O
CH2 – NC OH
CH2 – C – OCH 3

Benzyl isocyanide
+
CH2 = O + H + CH2 = O – H
18. Answer (3)
CH2 = OH
+ H
CH2 OH CH2 O
CH2 COOH '
+ CO 2 + H2 O
–H
+
CH2 COOH
CH2
CH2 OH
HCl
This compound does not form anhydride.
19. Answer (4)
CH 2 – Cl CH2 – NC
N { C–Ag
+ AgCl Rate of reaction v positive charge on carbonyl
carbon so E.W.G. increase rate while E.D.G.
14. Answer (2) decrease the rate.
(1)AlH(i–Bu)
(2) R — C { N 
2 H2 O
2
o R — CHO
O2N C – OC2H5 > Cl COOC2H5
AlH (i – Bu)2 is DIBALH which reduces nitrites to O
aldehydes. III > II >
15. Answer (4)
Alumina is an adsorbent (stationary phase)
COOC2H5 > MeO COOC2H5
Benzaldehyde is adsorbate.

Acetonitrile is mobile phase. I > IV

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20. Answer (3) 25. Answer (2)
C7H6O2 – A Phenol or unsaturated hydrocarbon (alkene or
alkyne) decolourised bromine water solution.
O
C2H5MgBr will react with carbonyl carbon or acidic
COOH C — NH2 hydrogen.
OH
aq·NH3 Br2, KOH
'
reacts with C2H5MgBr and also
A B
NH2 decolourized bromine water solution
26. Answer (1)
HCl
Aldehyde + Alcohol Acetal

C
more less steric
? A is Benzoic Acid reactive alcohol
21. Answer (4) aldehyde
? Best combination is HCHO and MeOH
27. Answer (2)
CO2Et NaOEt/' CO2Et

O O O O
O O OH
O H H
O

O
O O
' OH
Condensation
HO
C=O CO2Et +/'
H 3O
|
OEt O

22. Answer (4)

O
28. Answer (2)
CH3N
DIBAL-H followed by hydrolysis converts nitrile to
NaBH4 aldehyde and ester to aldehyde and alcohol.
OH
CHO
CH3NH
CN
DIBAL-H OH
23. Answer (2) O +
H3O H
COCH3 COOH O
O
KMnO4/KOH/'
CH3 H2SO4(dil) HOOC 29. Answer (3)
24. Answer (4) The reactivity order of carboxylic acid derivatives
depends on the leaving tendency of the leaving
O group. Higher the leaving tendency of the leaving
C CH group, higher will be the reactivity of the compound.
OEt (i) Ni/H2 N Therefore, reactivity order towards LiAlH4 is
CN (ii) DIBAL - H Acid halide > Acid anhydride > Ester > Amide

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30. Answer (2) 34. Answer (3)
Grignard reagent will not react with aldehydes if OH O
it has a functional group which contains acidic –
hydrogen. Options (B) and (D) have —COOH and CH — CH3 C—O
I 2/NaOH
—CH2OH respectively which contan acidic H-atom. + CHI3
31. Answer (1) OC2H5 OC2H5

OH
NH 2 NaNO2
CH3 O CH — CH 3
C H
+

O OH
OH OC2H5

+ o Reacts with Grignard’s reagent due to acidic


CrO3/H
hydrogen.
OH
OH o Fehling solution test is negative as there is
no – CHO group.
H 2SO 4 (conc.)/'
o Neutral FeCl3 test is negative as there is no
HO phenolic group
O
O 35. Answer (3)
O
32. Answer (3) C=O
H H

O O
OH
CH2Br NaBH4 CH2 Br Na OH (dil)
MeOH, 25ºC
O O
O OH
'
CH CH2
36. Answer (4)
LiAlH4 reduces esters to alcohols but does not
33. Answer (4)
reduce C = C.
CH3 – CH = CH – CO 2Me
CH 3
LiAlH 4

X is Meta cresol CH3 – CH = CH – CH 2


OH
CH 3 OH
37. Answer (2)
CH3 NaOH (10%)
OH OH
ONa OH
H2SO4(cat.)
CHCl3 O
OH NaHCO 3 (10%) C–O–Et
Insoluble O
O
Acid catalysed intramolecular esterification
Benzamide is amphoteric
OH OH OH
Oleic acid will dissolve in NaOH as well as
OH
NaHCO3 due to acidic nature. H+ –H
+

+O–H O
C–O–Et
O O O

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38. Answer (3) 41. Answer (2)
O O
O
C––CH3 C––O–Na+
CH 3 C CH3 CH3 CH 2 C HO
I2 + NaOH
+ CHI 3
Generally, aldehydes are more reactive than
CH3 CH3
ketones in nucleophilic addition reactions.
? Rate of reaction with alcohol to form acetal KMnO4
and ketal is
O O
O
C––OH C
CH 3 CH 2 CHO > CH 3 C CH3 D
O + H2O
39. Answer (1) C––OH C
O– O O

CH 2==O + OH o H—C—H C8 H6O 4 anhydride

OH 42. Answer (2)


O O

O
C—H + H—C—H
OH OH
OH CrO 3
+
H
O– O HO HO
Proton
C—H + C—H Exchange SOCl 2
H OH

OH O O
+
– H3 O O
C—H + H—C—O Cl
'
H
CH2OH + HCOOH HO HO

43. Answer (2)


40. Answer (3)
O O Alkaline KMnO 4 converts R with a
C––CH3 C––OH
benzylic hydrogen into benzoic acid.
1. NaOCl C2H 5 COOH
+
2. H
(ii) al ka line KMn O4
+
SOCl2 (ii) H 3O

44. Answer (2)


O
O OH
C––Cl
O
NaBH
 4
o
aniline EtO H
Ph––C––NH––Ph
NaBH4 does not reduces the double bond in E-J
unsaturated aldehydes/ ketones.
Only the keto group will be reduced.

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45. Answer (4) 50. Answer (2)

CH3 CH3 O
O H2O
CH3–CH–C CH HgSO4, H2SO4
H3C–CH–C–CH 3
NaBH4
H OH (1) EtMgBr (2) H2O
PBr3
CH3 OH
Br H3C CH3
C=C CH3–CH–C–CH3
Mg/Ether H3C CH2–CH3 H2SO4, '
CH2–CH3
†
O CO2 MgBr
51. Answer (4)
O
+
H
COOH
Br
Br2 Alc.KOH
hQ
46. Answer (3)
m-chlorobenzoic acid dissolves in aq NaHCO3 while
O3
m-chlorophenol dissolves in aq NaOH
47. Answer (4) –
CHO HO
Diborane selectively reduces carboxylic acid to H
– O O
alcohol in preference to other functional groups like
amide, carbonyl group and cyanide group. ' dil.NaOH

48. Answer (2)


O O

O
O3 CHO
Zn/H2O
CHO 52. Answer (2)
(X) (A) Attack of nucleophile on carbonyl centres depends
+
upon
[Ag(NH3 )2]

2 (i) Sterric factor


O 1
3 COOH (ii) Electronic factor
4 5 COOH ? Rate of reaction should follow the order
6
(B)
(ii) > (iv) > (i) > (iii)
53. Answer (4)
49. Answer (1) Increasing hindrence and electron
CH3 CH3 relasing group (ERG) attached on carboxyl group
CH3 MgBr decrease the reactivity.
H 3O
+ CH3
O CH3 HO Correct order of nucleophilic addition reaction is
CH3
Conc. H2SO 4

(A)
CHO
'

O
C H
O O3 /Zn, H 2O
CH3—CH2—C—CH3 < CH3—C—CH3 <
CH3
C C CH3 CH3 O O
CH3 CH3
H3C < CH3CHO

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54. Answer (3) 57. Answer (2)

– +
O
COO K CH2 – OH
Ozonolysis + C
(i) KOH O C2H5 C2H5
' C (ii) ' +
(A) (B)

(B) I2 + NaOH
? C is Ph – CHO HCOONa  CHI3 (Yellow ppt)
Ag 2O
CH3 COO  Ag p (Silver mirror)
CH3 O
(C) I2 + NaOH
Ba(OH)2 No Yellow ppt
' D CH3 – C == CH – C – CH3
' LiAlH 4 ZnCl2
C2H5  CH(OH)  C2H5  o
HCl

C2H5 – CH(Cl) – C2H5


O
58. Answer (1)
? D is CH3 – C – CH3
CHO

B is Ph – CH = C – CH3 CO, HCl (Gatterman koch


CH3 AlCl3 Reaction)

C{{N CHO
O
+
A is C6H5 – CH2 – C – CH3 SnCl2 + H3O (Stephen's
HCl Reduction)
55. Answer (1)

hydrolysis O
Ester  o Acid alcohol
(B) (C) C—Cl CHO
Since C gives turbidity immediately with Lucas
reagent (anhydrous ZnCl 2 + conc. HCl). This H2, Pd-BaSO4 (Rosenmund
means C should be 3° alcohol. Quinoline, S Reduction)

O CH3 59. Answer (66.67)


CH3 – COOH + CH3 – C – OH
O B
CH3 O
3° alcohol (C)
CH3 – C – CH2 – CH 3
56. Answer (3) (A) 1. CH3MgBr
+
2. H3O

COOH COOH OH
FeBr3 /Br2 CH3 – C – CH2 – CH 3

Br CH3
CH3 CH3
Cu/573 K
monobromo
' CaO derivative
CH3 – C = CH – CH3
CH3

CH3 A is C4H8O
Toluene
48
% of C= u 100 = 66.67
72
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60. Answer (4) Mo O
O2  CH3  CH2  CH3 
2 3
'
o CH3  CH2  CHO

Mn(OAc)2 – manganese acetate oxidizes alkanes


CH – C { N
to carboxylic acids in presence of O2 and heat.
CH3 64. Answer (4)
+
(i) C 2H5MgBr (ii) H3O NH2–NH2
O C2H5O Na
– +

O
CH – C – C2H5
65. Answer (1)
CH3 CrO H SO
(A) CH3CH2OH 
3 2 4
Jones reagent
oCH3COOH

In the rest of the options acetaldehyde will be


(i) CH3MgBr (ii) H2O formed.
OH 66. Answer (3)
* – C*– C H
* CH H3O
+

2 5 CH3 CH2 CN ' CH3 – CH2 – COOH


* O
CH3 CH3 SOCl 2
(B) CH3– CH2 – C – Cl

Pd/BaSO 4, H2
Number of chiral centres in the product (B) = 4.
61. Answer (1) O
CH3 CH3 – CH2 – C – H
CH3—CH2—CH—O—COCH2—CH—CH2—CH3
Correct option should be (3)
Hydrolysis
CH3 67. Answer (4)
CH3
COOH OH
CH3—CH2—CH—OH + HOOC—CH2—CH—CH2—CH3
[B] O2N NO2
CH3
[C] and are acidic
CrO3—H2SO4
NO2
CH3—CH 2—C==O
enough to liberate CO2 with NaHCO3 solution.
CH3
68. Answer (1)
62. Answer (4)
O
O OH C2H 5

O + CH3 COCl Zn – Hg
AlCl3 HCl
O (i) H 2SO 4
(ii) NaOH Br2 /AlBr3

O
C2H 5 C2H 5
O NO 2
HNO 3/H2 SO4

HO OH Br Br
Derivative of phenolphthalein
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69. Answer (3) 73. Answer (1)
H2 /CO
CH3CH2 CH = CH2 CH3 CH2CH2 – CH2 – CHO CH2 OH
Rh catalyst
CHO –
HCHO, OH
70. Answer (1) + HCOO

(cannizzaro
The structures of the given compounds are CH3O reaction))
OCH3
SO3H
NaH


CH2OC2H 5 CH2 – O
(A) Sulphanilic acid
C2 H5 Br
NH2
HI
OH OCH3 OCH3
O2N NO2 CH2I

(B) Picric acid + C2H5 OH + CH3OH

NO2
OH

OCOCH3 74. Answer (4)


COOH
(C) Aspirin O OH
CH2 – CH 2 – CH CH2 – CH 2 – CH
NaOH

HO CH2 – CH – CHO CH2 – CH


H – OH CHO
O O '
(D) Ascorbic Acid HO CHO

OH OH

? Only 1 compound has –COOH group


75. Answer (3)
71. Answer (4)
DIBAL-H – diisobutylaluminium hydride selectively
reduces nitriles and esters to aldehydes.
O
Cl Cl Hydrolysis O
O OH
373 K H
i) DIBAL-H, Toluene, –78°C
(C 4H8 Cl2) (C4H 8O) ii) H 3O
+

O
A B
P
B is a ketone, cannot give Tollen’s test. 76. Answer (3)
A o 2, 2-Dichlorobutane
(i) O3
B o Butan-2-one HC C CH2 CH3 (ii) Zn

So correct option should be (4) O


72. Answer (1) H C C CH2 CH3
O
2,4 DNP test is used to identify – C – group. It O
[Ag(NH3 )2]NO 3
gives addition reaction with carbonyl compounds. O
So, it can be used to identify aldehyde in the given –
Ag + O C C CH2 CH3
option. It gives yellow/orange PPt with carbonyl
(bright silver
containing compounds. O
mirror)

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77. Answer (2) 83. Answer (2)
CH 3 COO H CN COOH
(1) KMnO 4/OH–
(2) H +
H2 O H2 O
+ +
H H
OCH3 OCH3

78. Answer (4) 84. Answer (4)

C6 H5
C N G– G+ C = N MgBr
C6H5MgBr (1 eq) O O O–
ether
H
H –
OCH3 OCH3
OH–

H 3 O+ O O O
O–

C6 H5 –
+
C=O

H2O

OCH3
O
OH
79. Answer (4)
Mesityl oxide is the common name of aldol
condensation product of acetone. Its structure and
IUPAC name are X
O O
O OH
+
H
+ H2O
Heat
CH3
Y

80. Answer (3)


Ethylene glycol in presence of H + will convert
ketone into cyclic ketal and the ester group 85. Answer (2)
remains intact. +
RCHO + 2 ¬ª Ag NH3 2¼
º  3OH– 
o
O O Ethylene Glycol
O O
O RCOO + 2Ag + 2H2O + 4NH3
H+
OC 2 H5
OC2 H5 for 1 mol of R-CHO, 2 mol of [Ag(NH3)2]+ is reduced.
81. Answer (1) +
2 ª¬ Ag NH3 2¼
º + 2e – o 2Ag + 2NH3
CH3 COOH
Alk. KMnO4
86. Answer (3)
H+ O O

OCH 3 OCH3
+ NH2 C NH NH 2
82. Answer (1) O
Reaction occur through formation of carbocation.
N–NH– C–NH 2
O OH Cl o
C 2H 5MgBr Lucas
H 2O Reagent

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87. Answer (4) 90. Answer (2)
O
OH OH
O
1. CH3MgBr (excess)
+
2. H3O
(II)
OH
O
Aldehyde gives Silver mirror test with Tollen’s O OH
1. CH3MgBr (excess)
reagent but not ketones.
+
O 2. H3 O

O – O CH3
OH H
+ CH 3 C CH3
O H O
(IV) gives test OH
O –
O O
[Ag(NH 3)2 ] OH
+ – C
R C H CH3 CH3MgBr (excess) C
H2 O CH3
CH 3
+
O H 3O
OH –O
R C OH + 2Ag + 4NH3 + 2H2O OH

88. Answer (1)


This problem is based on intramolecular aldol
condensation reaction. OH
91. Answer (3)

O O OMgBr
O H – C2H 5MgBr, dry ether
O CH2
CHO C O
O
OH
O O O
OH H 2O , HCl
O O
+
alcohol H OH
'
O O

Cl
P(major product)
92. Answer (3)
89. Answer (1)
O O OH
O
Order of hydrolysis
O O H
O
NaOH
R – C – Cl > R O R
O O
–I > + M
+M>–I
– +
I2/NaOH O Na
O O Iodoform reaction
> > R – C – NH2 Filtrate + HCl
R OR
+M>–I
O O
+M>–I
–NH2 has greater denoting power than –OR group
making –C = O less electron deficient. OH

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93. Answer (2) 98. Answer (3)
Maleic anhydride can be prepared by heating O O O
cis-but-2-enedioic acid C
OH S
Cl C
Cl Cl + HCl
N NH2
N NH2
O O H |
H

O
H C H C
C
C OH Heat C Cl
O + H2On N
+
NH3Cl

C OH C |
H
H C H C
CH3OH
O
O O C
OMe
NH2HCl
94. Answer (2) N
|
H

99. Answer (1)


Et O H (excess) OEt
Br CHO Br CH H2 SO 4
dry HCl (a) CH3 COOCH2CH3 
H O
o
2

OEt CH3 COOH  CH3 CH2 OH


(acetal)
DIBAL-H
(b) CH3 COOCH3 o
H O
CH3  CHO
– 2
tBuO
SnCl , HCl
OEt (c) CH3 C { N 
2
HO
o CH3  CHO
H 2C = C 2

OEt
O
CH3MgBr
95. Answer (4) (d) CH3C { N CH3 – C – CH 3
H3O

CN CH3C = NMgBr So, the correct match is


(a)-(ii), (b)-(iii), (c)-(iv), (d)-(i)
CH3MgBr
(1 eq) Cyanides can be converted to aldehydes by
DIBAL-H/H2O as well.
+
H3O 100. Answer (1)
O
O OH OH
C NaOH (X) CN LiAlH 4 NH 2
H HCN, H O
CH3
+
2 H H3O
Y

(P) Addition of HCN to aldehydes and ketones occurs


slowly because HCN is weak electrolyte and does
P can give Iodoform test not produce enough CN– ion. A catalytic amount of
base can fasten the reaction.
96. Answer (2)
HCN  OH o H2O  CN
i) DIBAL – H
R – CN ii) H O R – CHO –
2 O O
+ H H2O
97. Answer (1) CN

H
CN

O
COO –Na+
CH3 Br 2 OH OH
+ CHBr3 LiAlH4 / H 2O
NaOH NH2
H
CN H
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101. Answer (1) 105. Answer (4)

CH3  C { C  H  NaNH2 o CH3  C { CNa  NH3 (g) CH 3 CH3


(A ) BrMgN=C –
O MgBr
+

NC O
2CH 3MgBr
CH 3
OH
CH3
+
H3O
O
(A) CH3
C O=C OH
OH H3C H 3O +

CH 3
| H2
CH3  C { C  CH2  CH2  CH CH3
(B) Pd /C 106. Answer (4)
OH CH3COOH + SOCl 2 CH 3COCl
|
CH3  CH2  CH2  CH2  CH2  CH CH3 (A)
(C)
C6H6 AlCl 3

O
|| KCN / H2 O
CrO3
o CH3  CH2  CH2  CH2  CH2  C  CH3
(D)
HO – C – CH3 O = C – CH3
Note : The anion of (A) is a strong base and on (B)
its reaction with 4-bromobutan-2-ol, it is likely to CN
(C)
pick up proton from alcohol. But looking at the
options, nucleophilic substitution is considered to 107. Answer (1)
get (B). –
O O
102. Answer (2)
H H
Aldehydes and ketones having 3 D-hydrogen atoms Na OH
+ –
OH
undergo haloform reaction with NaOCl. The '
HOH2C
carbonyl compound may or may not have a double HOH2C
bond. –
O O
O
H H
NaOCl OH
CH3–CH=CH–C–CH3 –CHCl3
+
O O HOH 2C HOH2C
+
– + H3O
CH3–CH=CH–C–ONa CH3–CH=CH–C–OH
103. Answer (3) O OH
– +
Mg O Na
CH3 CH2 CH2Br CH3 CH2CH 2MgBr
+
O=C= O HOH2C
OH

O H3O
+
diol
+
H 3O
CH3 CH2 CH2COOH CH3CH2CH 2 C –
O MgBr
Butanoic COOH
Acid
104. Answer (3)
HOH2C
O 108. Answer (4)
CH 3MgBr + –
BrMg
O – • Na in presence of H2, will not release electron
O
which are required for reduction.
For 1 mole o 3 moles of CH3MgBr is used.
• H2 gas also not get adsorbed on Na. Hence
(2 moles required for ester and 1
mole for acidic H of ethyne) Na/H2 cannot be used as a reducing agent

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109. Answer (3)
7.8
LiAlH4 56 u 100
CH3 CH 2 CH2 COO CH 2 C H3 ? 64
H 3O
+
x
74
CH3CH 2OH + CH3CH 2CH 2CH2OH
x | 16
Oxidation 113. Answer (2)

CH 3COOH + CH 3CH2CH 2COOH O O


C 4 - Carboxylic CH2 – OH HO – C CH2 – O – C
acid +
CH2 – OH HO – C CH2 – O – C
110. Answer (2)
O
+
O
H 3O 210°C
CH3 – CH = CH 2 CH3 CH CH 3
(A)
OH CH2
(major)
KIO/KOH CH2
CH3COOK + CHI 3
(B) (C) 114. Answer (4)
111. Answer (1) O
– +
O ONa SO 3H
+ NaHSO 3 CH3 give orange ppt with
R R R R
2, 4-dinitrophenyl hydrazine.
Proton transfer
115. Answer (1)
Statement (I) is correct as monocarboxylic acids
OH SO 3Na
with even number of carbon atoms show better
R R packing efficiency in solid state, statement (II) is
Crystalline solid
also correct as the solubility of carboxylic acids
decreases with increase in molar mass due to
increase in the hydrophobic portion with increase in
O OH
Base the number of carbon atoms.
+ HCN
H 2O
R R R R 116. Answer (3)
CN
Cyanide as final is a conjugated diketone.
product not amine

112. Answer (16) In rest of the diketones given in the question, the
3-Hydroxy propanal o Acrolein two (C = O) groups are not in conjugation with each
Let xg 7.8 other.

7.8
Moles of acrolein produced = moles
56

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117. Answer (4) 119. Answer (3)

120. Answer (1)


SOCl
CH3 – CH2 – CH2 – OH 
2
o
Propan-1-ol

KCN
CH3 – CH2 – CH2 – Cl  o
H /Ni
CH3 – CH2 – CH2 – CN 2
Na(Hg)/C H OH
o
2 5

CH3 – CH2 – CH2 – CH2 – NH2


n butyla min e

121. Answer (2)

S+
Br MgBr
S–

2Mg, THF
2 2

'A' O
C – O – CH3

O–

Hence, the correct option is (4).


118. Answer (3)
Given compounds : H2O/H
+

OH

Number of electrophilic centres = 3


Hence ‘A’ is bromobenzene.

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122. Answer (3) 126. Answer (3)
C will not give acetophenone Benzoic acid can be converted to benzaldehyde in
presence of MnO.
127. Answer (1)

123. Answer (3)


In order to form enamine from the reaction of
carbonyl compound with 2º amine, the carbonyl
compound must have D-hydrogen.
128. Answer (3)
O

In C No D-hydrogen is present. (A)

t-Bu t-Bu
Along with this, due to steric crowding by t-Bu
group, it is difficult for 2º amine to attack on this
compound.
124. Answer (1)

(B)

(C)

(D)
125. Answer (2)

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129. Answer (4) 132. Answer (3)
The six possible forms of diaminobenzoic acid are
COOH COOH
NH2
; ;
H2N NH2
NH2
(1) (2)
COOH
H2N NH2 NH2
–CO2

NH2
(3) (A)
COOH COOH NH2

NH2 NH2
–CO2
;
NH2 NH2
NH2 (B)
133. Answer (2)
COOH NH2
NH2
–CO2
134. Answer (1)
H2N Esterification of carboxylic acid with an alcohol is
NH2 nucleophilic acyl substitution and presence of
(C) electron withdrawing group in the carboxylic acid
Melting point of product (C) = 142ºC increases the rate of esterification reaction.
130. Answer (1)
135. Answer (1)

zymose NaOI
C6H12O6  o C2H5 OH  o
HCOONa  CHI3
(B)

136. Answer (4)

131. Answer (3)

Total 4S electrons are there. Reaction is aldol


condensation.
4-methyl-6-nitro-3-oxohept-4-enal

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137. Answer (4) 141. Answer (3)

OH

Na2Cr2O7, H2SO 4/H2O is the strongest oxidising


agent and it will oxidise 1° alcohol into acids.
138. Answer (2)

142. Answer (4)

143. Answer (1)

DIBAL-H reduces both the cyanides and esters to


aldehydes.

2 chiral carbons are there in product A.


139. Answer (2) 144. Answer (3)

145. Answer (1)


140. Answer (1)

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146. Answer (02.00) 150. Answer (2)
In the complex present in Fehling’s reagent, Cu+2
ion is present.
So, spin only magnetic moment
= 1(1  2)
CN
3  2 B.M
147. Answer (530)

5
Moles
92
Moles of benzaldehyde produced
5
u 0.92 0.05
92
? Mass of benzaldehyde formed
= 0.05 × 106 2nd reaction is the cross aldol reaction.
151. Answer (1)
= 5.3 g
= 530 × 10–2
148. Answer (3)

J-Methyl cyclohexane carbaldehyde


152. Answer (3)

Number of stereoisomers = 3
153. Answer (3)

149. Answer (4)

‰‰‰
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