Professional Documents
Culture Documents
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
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
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)
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]
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
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]
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)
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
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
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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
(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
(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
CONH2 CH3
COCH3
(3)
HOH2 C
O CH3
CN
[JEE (Main)-2020]
(1) LiAIH4 (2) NaBH4 (4)
(3) H2/Pd (4) B2H6 O CH3
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50. The major product (Y) in the following reaction is CHO
CH3 (iii)
HgSO4, H2SO4 OCH3
CH3–CH–C CH X
H2O
CH3
(1) CH3–CH–C=CH–CH3 (1) (iii) < (iv) < (ii) < (i)
[JEE (Main)-2020]
O
(3) (4) II
(1)
C6H5 C CH2 CH3
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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
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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
?
64. OH
O
NO2 NO2
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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.
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O (i) C6H5MgBr Ether
O CN (1.0 equivalent), dry
X
i) DIBAL-H, Toluene, –78°C 78. (ii) H3O
+
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
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
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
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,'
+
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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)
(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
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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)
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 NH2HCl
H OH
NH 2
(3)
X – NaOH Y- H
(4)
N NH2HCl
HHCl
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]
(1) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i) (3) CH3 – CH = CH – CH2 – CH2 – CH2 – COOH
Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
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
[JEE (Main)-2021]
CH2 – CH2 CN
(3)
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
(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
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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
Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456
121. In the given reaction
OH 124.
‘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)
(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)
[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)
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[JEE (Main)-2022]
(1) (2)
(3)
(3) (4)
140.
(4)
(2)
[JEE (Main)-2022]
(3) (1) CH3 – C { N (2) Ph – C { N
143.
(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.
148.
(4)
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)
(1)
(2) (2)
(3)
(3)
(4)
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Chapter 26
Aldehydes, Ketones and Carboxylic Acids
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)
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.
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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
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–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 O O
+
– H3 O O
C—H + H—C—O Cl
'
H
CH2OH + HCOOH HO HO
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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
O
O3 CHO
Zn/H2O
CHO 52. Answer (2)
(X) (A) Attack of nucleophile on carbonyl centres depends
+
upon
[Ag(NH3 )2]
(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
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)
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
O
CH – C – C2H5
65. Answer (1)
CH3 CrO H SO
(A) CH3CH2OH
3 2 4
Jones reagent
oCH3COOH
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
NO2
OH
OH OH
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
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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
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
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
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
OEt
O
CH3MgBr
95. Answer (4) (d) CH3C { N CH3 – C – CH 3
H3O
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)
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)
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)
KCN
CH3 – CH2 – CH2 – Cl o
H /Ni
CH3 – CH2 – CH2 – CN 2
Na(Hg)/C H OH
o
2 5
S+
Br MgBr
S–
2Mg, THF
2 2
'A' O
C – O – CH3
O–
OH
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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)
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)
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137. Answer (4) 141. Answer (3)
OH
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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)
Number of stereoisomers = 3
153. Answer (3)
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