Khattar Advance Question
Khattar Advance Question
Me Me Br Br Me Me
Me Me
I II III IV
(a) I, III and IV (b) I, II and III (c) I and III (d) III and IV
2. In the following reaction, the major product T is:
Me
(i) NaOMe
Br T
(ii) H3O+, reflux
O (iii) polyphosphoric acid
Me
Me Me
P
W
6. For each of the following pairs, identify the correct match.
Column-I Column-II
CH3 H CH3
CH3
CH3
CH3
(Q) CH3 H H3C (ii) Enantiomers
H H
H
CH3 CH3
H H
(R) (iii) Diastereo isomers
CH3 CH3
H H
H3O+
9.
DMSO
2
The Me-Cha-Nism Mantra PW
O
CH3 H2N — NH2
10. H3C
OH
O
Which of the following is the major product?
HO
(a) (b) (c) (d) CH3 C C CH3
O
C OMe
conc
11. Ph Ph H2SO4
Ph
The major product of this reaction is:
O
C OPh Ph O Ph Ph OH
Ph
F
Excess
12. BF3
D
OH
The major product of this reaction is
BF4
O OH
OH
13. What is the relationship between products formed?
O
H+
HO(CH2)3 C (CH2)3OH Acetal
(a) Enantiomers (b) Diastereomers (c) Positional isomers (d) Functional isomers
O
H+
14. D
O
The major product of the reaction is:
O O
(a) (b)
HO HO
O
(c) O (d)
HO HO
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15. 1 Eq
HBr
Br
(a) (b) (c) (d)
Br Br Br
O
14 15 D+
N N C
16. NO2
NO2
O
14 15
+ O
(c) D N N (d) 14 15
D N N +
C
1 Equivalent
17. Br – Cl
18. COOH
D2SO4
D
4
The Me-Cha-Nism Mantra PW
NH2
19. NaNO2 Base
HCl/0-5°C D
20.
HBr
Br Br
Br
(a) (b) (c) (d)
Br
O
O
21.
Br Br
NaNH2 O
(excess) Z D W
O O
O
(a) (b) O (c)
O O (d)
O
O O
O O
O O
O
22. Nitration of A can give rise to seven possible products (b – h) in principle.
NO2 NO2 NO2 NO2 NO2
O 2N
HNO3
H2SO4
O 2N
(a) (b) (c) (d)
NO2 NO2
NO2 NO2
NO2
NO2
NO2 NO2
(f) (g) (h)
(e)
However, only three are produced. Identify the correct set of products.
(a) d, e, f (b) b, c, h (c) b, d, g (d) e, f, h
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23. Consider the two compounds A and B shown below. A B
O O
CH3
Identify the correct observations upon standing an enantiomerically pure form in a solution of NaOEt.
(a) A losses its optical activity
(b) B losses its optical activity
(c) Both A and B losses its optical activity
(d) Neither A nor B losses its optical activity
24. Consider the following sequence of reactions.
O
C 1. BrCH2(CO2Et)2 1. PhCH2Cl
NK A B
2. C2H5ONa 2. HCl, H2O, heat
C
O
The major final product (B) is:
(a) H2NCH2COOH (b) PhCH2CH(NH2)COOH (c) PhCH(NH2)COOH (d) PhCH2C(COOEt)2
NH2
C6H5NHNH2
25. The product formed in the reaction C6H5CHOHCOC6H5 is:
(excess)
C6H5 C6H5 NNHC6H5 C6H5 O C6H5 OH
CHOH C C CH
(a) (b) (c) (d)
C C C CH
C6H5 NNHC6H5 C6H5 NNHC6H5 C6H5 O C6H5 OH
H+
Ph C OC2H5
O
the major product formed is:
O O
OH OH
6
The Me-Cha-Nism Mantra PW
The products (B) and (C) are respectively.
OH O
NMe2 NMe2
Br Br Br Br
(a) and (b) and
Br Br
Br CF3 Br Br Br CF3
Br
O NMe2 OH NMe2
Br Br Br Br
(c) and (d) and
CF3 Br Br CF3
Br Br
Br Br Br
28. For the reaction
O
1. MeMgBr (excess)
O
2. H3O+
O
the product expected is:
O O
Me OH
CHOHCH3
(a) O (b) O (c) O (d)
CHOHCH3
Me OH Me OH Me Me
29. The product of the reaction is:
OH
HCl
+ PhCOCH3 heat
CHO
+ –
O PhCl OH OCH2COPh O OH
(a) (b) (c) (d) Ph
CH CHCOPh CHO
NH3 excess
30. The major product of the reaction is: CH3COCH2CH2COCH3 heat
H3C CH3
(a) H3C C C CH3 (b) H3C CH3 (c) H3C CH3 (d)
HO OH
H2N NH2 N H2N NH2
NH NH H
31. Consider the following reaction.
OH
+ H2NCH2CH2COOH → pantothenic acid
O O
The structure of pantothenic acid is
OH H
N
(a) (b) COOH
COOH
O N O O
O
COOH
(c) HO N (d)
H COOH
OH O N
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32. The product formed in the reaction
KOH, EtOH
+
Br
A B C
In an experiment, 1.99 g of bromide A on reaction with ethanolic potassium hydroxide gave 1.062 g of a mixture of the olefins
B and C. If the ratio mass of olefins B : C formed is 2 : 1, the yields for their formation, respectively, are
(a) 60 and 30% (b) 50 and 25% (c) 66 and 33% (d) 54 and 27%
35. Consider the following reaction sequence
OH OH OH
Sn/HCl Ac2O
OH 90% 90%
(P)
HNO3 O2N H2N AcHN
70%
OH OH OH
Sn/HCl Ac2O
90% (Q)
90%
NO2 NH2 NHAc
(25%)
The overall yield for the formation of (P) and (Q), respectively, are approximately.
(a) 57% and 20% (b) 57% and 68% (c) 83% and 68% (d) 83% and 20%
36. The correct statement with respect to the stereochemistry of a-hydroxy acids P and Q formed in the following reactions is:
Br
OH Ag2O
P Me CO2H Q
H2O, OH
(a) Both P and Q are formed with retention of configuration.
(b) Both P and Q are formed with inversion of configuration.
(c) P is formed with retention of configuration and Q with inversion of configuration.
(d) P is formed with inversion of configuration and Q with retention of configuration.
8
The Me-Cha-Nism Mantra PW
37. Among the following, the most suitable reagent for carrying out resolution of racemic 3-methylcyclohexanone is:
OH Me OH OH
CO2Me
(a) (b) Ph CO2H (c) MeO2C (d)
OH OH HO
38. During a lab experiment, Pankaj Sir prepared four isomeric para-disubstituted aromatic compounds P, Q, R and S with molecular
formula C8H8O2. Based on the following observations, identify structures of the compounds.
(i) Both P and Q form a silver mirror with Tollen’s reagent; also Q gives a positive test with FeCl3 solution.
(ii) R gives positive iodoform test.
(iii) S is readily extracted in aqueous NaHCO3 solution.
Which among P, Q,R and S does contain phenolic group?
(a) P only (b) Q only (c) Both P and Q (d) Both Q and R
39. Dicoumarol (X) is an anticoagulant. The number of possible monochloro substituted isomeric derivatives and the volume of
hydrogen liberated at STP by the reaction of 0.5 mol of dicoumarol with sodium are respectively
(a) 5, 22.4 dm3 (b) 5, 11.2 dm3 (c) 6, 11.2 dm3 (d) 4, 22.4 dm3
O
40. (conc. HCl + Zn-Hg)
O
O O
O
(a) (b) (c) (d)
OH
41. The major product formed in the following reaction is
NaOMe, MeOH
→
(a) (b)
(c) (d)
42. In the following set of Aromatic compound (e.g. P, Q and R). Find the sum of the total no of position isomers in all the given
compounds.
C6 H 4 XY, B3 N 3 H 4 XY C6 H 3 XYZ
(P) (Q) (R)
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43. The structure of Q in the following reaction scheme is
CHO
HO H
PhNHNH2 (excess) PhNHNH2 (excess) H 2 ,Ni
H OH N P Q
H OH
CH2OH
CH2OH CH2 OH CH2OH CH2OH
HO H H OH H OH HO H
(a) H OH (b) H OH (c) HO H (d) H OH
H OH H OH H OH HO H
CH2OH CH2 OH CH2OH CH2OH
44. The major product formed in the following reaction is
CF3COOH/H2O
o 2
CHCl3; 0 C, 1h
3 3
(a) (b)
(c) (d)
CH2
H O+
46. O
3
→ A, A is
CH3 OH
OH OH
HO
10
The Me-Cha-Nism Mantra PW
48. One mole of triphenyl methanol dissolved in 100g of 100% H2SO4 lowers freezing point
(a) Twice as much as one mole of methanol does
(b) As much as one mole of methanol does
(c) Thrice as much as one mole of methanol does
(d) No lowering in freezing point
49. Rank the organic amines shown below in the order of increasing pKa values.
(a) D < A < C < B (b) C < A < D < B (c) A < D < B < C (d) D < C < B < A
50. Many times enantiomers give rise to different odors. For example, (–)-Carvone (I) has sweetish minty smell and (+)-Carvone (II)
has a spicy aroma, like Persian cumin seeds. Similarly, (+)-Limonene (III) is found in oranges and (–)-Limonene (III) is found in
lemons. What would be the stereochemical descriptors of their absolute configurations?
(a) (I)-R, (II)-S, (III)-R, (IV)-S (b) (I)-S, (II)-R, (III)-S, (IV)-R
(c) (I)-R, (II)-S, (III)-S, (IV)-R (d) (I)-S, (II)-R, (III)-R, (IV)-S
51.
To distinguish between the above isomeric hydrocarbon molecules, which will work best?
(a) Bromine water test (b) O3/H2O, heating and passing evolved gas through lime water
(c) O3/H2O, ∆, I2/NaOH (d) Tollen’s test
52. Among the following compounds most basic amino acid is :
(a) Lysine (b) Asparagine (c) Serine (d) Histidine
53. When each of A and B undergoes reaction with KOH in methanol the rate of reaction
(a) is very slow for A compared with that of B. (b) is very slow for B compared with that of A
(c) is equal for both A and B (d) there is no reaction possible
54. In the following reaction, compound Q is
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55. The correct sequence of reactions for the synthesis of the following molecules is(are)
(a) (i) 4-Iodophenol, Mg, ether ; (ii) Cyclopropane carboxaldehyde, THF ; (iii) MeMgBr ; (iv) MeI, THF
(b) (i) Cyclopropyl bromide, Mg, ether ; (ii) 4-Hydroxybenzaldehyde, THF ; (iii) MeMgBr ; (iv) MeI, THF
(c) (i) 4-Iodophenol ; (ii) MeMgBr ; (iii) MeI, THF ; (ii) Mg, ether ; (iii) Cyclopropane carboxaldehyde, THF
(d) (i) Cyclopropyl bromide, Mg, ether ; (ii) Methyl 4-methoxybenzoate (limited), THF
56. The major product formed in the following reaction sequence is
i. EtMgBr, Et2O
ii. H2O
iii. Ph3P=CH2, THF
57.
(b) Following molecule is highly polar and the rotational barrier of central C–C bond is very small
(c) 3-methylenecyclobut-1-ene has been prepared and has no tendency to rearrange to 1-methylcyclobuta-1,3-diene
(d) The ionisation constant for 9-chloro-9-phenylfluorene in liquid sulphur dioxide is much less than that of analogous
triphenylmethyl chloride
12
The Me-Cha-Nism Mantra PW
59. Consider the following conjugated diketo compounds
Which of the following is the correct decreasing order of E° values?
(a) I > II > III (b) III > II > I (c) I > III > II (d) II > I > III
60. Which of the following is correct comparison of heat of hydrogenation of the following alkenes?
(a) II < IV < III < V < I (b) III < IV < I < V < II (c) V < IV < III < I < II (d) IV < V < I < III < II
The correct decreasing ease of hydrolysis is
(a) II > III > IV > I (b) II > IV > III > I (c) II > I > III > IV (d) IV > II > III > I
63. Product
O
Heat
64. + CCl3CONa Product.
13
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65. Predict the product of the following reaction
66. Which of the following is most reactive in base catalyzed decarboxylation reaction?
67. Indigotin has following isomers I and II. The correct statements for these isomers are
(1) I, II are diastereomers
(2) I, II are optically active
(3) II is more stable than I due to intramolecular hydrogen bonding
(4) II is more polar than I
(a) 1, 4 (b) 2, 3 (c) 1, 3 (d) 2, 4
68.
Identify A
69. Phenol reacts with acetone in the presence of conc. sulphuric acid to form a C15H16O2 product. Which of the following correspond
to this product?
(a) (b)
(c) (d)
14
The Me-Cha-Nism Mantra PW
70. Which of the following starting material would generate allopregnane, when treated with H2/Pt?
71. Which of the following polycyclic aromatic compounds(s) is most likely to undergo electrophilic addition reaction?
72. When triphenyl carbinol (C6H5)3COH is treated with acidic H2O2, then
(a) A 50:50 mixture of benzophenone and phenol is produced
(b) Only Benzophenone is produced
(c) Only Phenol is produced
(d) None of these
73. Compare the relative ease of substitution of labelled chlorine by –OCH3 in aromatic nucleophilc substitution reaction.
(a) II < I < III (b) III < II < I (c) III < I < II (d) I < II < III
74. A C9H12O compound is reacted with a solution of lithium in liquid ammonia. After evaporation of the ammonia, the residue is
warmed with 10% HCl and extracted with ether. The product is identified as 3-cyclohexenone. Which of the following might be
the starting compound?
(a) C6H5OC3H7 (b) C6H5CH2CH2CH2OH
(c) C6H5CH2CH2OCH3 (d) C6H5CH2CH(OH)CH3
75. Choose the major product of the following reaction sequence
(a) (b)
(c) (d)
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76. Heating a mixture of 1, 3-diphenyl acetone and acrolein in trimethyl amine gives a product C18H16O in 53% yield. The mechanism
for the product formation is believed to be a Michael addition followed by an intermolecular aldol condensation. Which is the
product of reaction?
77. Identify the reactions leading to correct major products in the following reaction
(a) (b)
79. To find molecular mass of base (acidity = 4) by chloroplatinate salt method, following graph is plotted (where y = ω of platinum
salt, x = ω of residue, here ω refers to weight).
Molar mass (in g/mol) of base will be:
80.
on reaction with Baeyer’s reagent gives a product containing x no. of ‘O’ atoms , ‘y’ no. of sp3 carbons , ‘z’ no. of sp2 carbons.
Consider the following statements :
S1 :x is the sum of structural isomers of C6H14 and C4H8
S2 : y is the no. of ‘H’ atoms in an alkane whose no. of isomers are half of the isomers of C4H8.
S3 : The no. of cyclic isomers of Cz H2 are equal to (y – z).
Z
S4 : x — z is the no. of isomers of C3 H6Cl2.
How many statements are correct :
(a) 1 (b) 2 (c) 3 (d) 4
16
The Me-Cha-Nism Mantra PW
81.
(a) (b)
(c) (d)
(a) (b)
(c) (d)
84. Which would produce chiral molecule after treatment with Lindlar's catalyst?
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85. Identify the product R in the following reaction
86. Sulphanilic acid has both acidic and basic groups. It is soluble in:
(P) Organic solvents (Q) Water
(R) Alkalies (S) Mineral acids
(a) S only (b) Q, R and S
(c) R only (d) R and S both
87. Identify the product of the reaction
89. The correct sequence of the amino acids present in the tripeptide given below is
Me OH
Me Me O
H
H2N N N OH
H
O O
OH
(a) Val-Ser-Thr (b) Val-Thr-Ser (c) Leu-Ser-Thr (d) Leu-Thr-Ser
90. Major product formed in the given reaction is:
acetone (excess)
a-D-glucose H+
OH O
Me Me H
O OH O O
(a) Me (b) Me O Me
O H O Me
O OH
HO H
H
OH H O O
Me HO Me
O O
(c) Me Me (d) Me
O O
O O Me H
O Me O
Me
18
The Me-Cha-Nism Mantra PW
91. Correct characteristics of the functional groups of adenine in DNA base pair are: 10
NH2
(a) N(3) is a hydrogen bond acceptor and C(6)-NH2 is a hydrogen bond donor 7 6
N 5
N1
(b) N(1) is a hydrogen bond acceptor and C(6)-NH2 is a hydrogen bond donor 8
2
(c) Both N(3) and C(6)-NH2 are hydrogen bond acceptors 9N 4 N
3
(d) Both N(1) and C(6)-NH2 are hydrogen bond acceptors H
adenine
92. A polymer sample has the following composition:
Number of molecules Molecular weight
10 1000
50 2000
40 4000
The polydispersity index (P.D.I) of the polymer is:
(a) 85000/27 (b) 85/81 (c) 850/729 (d) 729/850
93. A tripeptide on treatment with PhNCS (pH = 8.0) followed by heating with dilute HCl afforded a cyclic compound M and a
dipeptide. The dipeptide on treatment with PhNCS (pH = 8.0) followed by heating with dilute HCl afforded a cyclic compound N
and an acyclic compound O. The CORRECT sequence (from N-to C-terminus) of the tripeptide is
S S
Ph Ph
NH2
M= N NH ; N = N NH ; O = HO2C
O O Ph
(a) glycline-phenylalanine-valine (b) valine-phenylalanine-glycine
(c) glycine-tyrosine-valine (d) glycine-phenylalanine-alanine
94. The correct match for the compounds in Column-I with the property in Column-II is:
Column-I Column-II
(P) Dichlorodifluoromethane (i) Antiseptic
(Q) Sulfapyridine (ii) Insecticidal
(R) Furacine (iii) Antibacterial
(S) Hexachlorobenzene (iv) Ozone layer depletion
(a) P-(ii); Q-(i); R-(iv); S-(iii) (b) P-(iv); Q-(i); R-(ii); S-(iii)
(c) P-(i); Q-(iii); R-(ii); S-(iv) (d) P-(iv); Q-(iii); R-(i); S-(ii)
95. Among the following, the correct statements about ribose is are:
1. On reduction with NaBH4 it gives optically inactive product
2. On reaction with methanolic HCl it gives a furanoside.
3. On reaction with Br2—CaCO3—water it gives optically inactive product.
4. It gives positive Tollen’s test.
(a) 1, 2 and 4 (b) 1, 2 and 3 (c) 2 and 3 (d) 4 only
96. The amino acid constituents of artificial sweetener given below are
COOH
H
N COOH
H2N
O Ph
(a) D-Glutamic acid and L-phenylglycine (b) L-Glutamic acid and L-phenylalanine
(c) L-Aspartic acid and L-phenylalanine (d) L-Aspartic acid and L-tyrosine
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97. The most basic amino acid among the following is
(a) tyrosine (b) methionine (c) arginine (d) glutamine
98. The incorrect statement regarding the major product (D) obtained in the following reaction sequence is:
HS(CH2)3SH BuLi CH3Cl HgCl2/CdCO3
Ph—CHO A B C D
H2O
(a) It gives positive Tollen’s test (b) It gives positive lodoform test
(c) It shows tautomerism (d) Its degree of unsaturation is 5
99. A mono-acid organic base gave the following results on analysis: C = 78.6%, H = 8.4% and N = 13.0%. 0.4 g of the platinichloride
salt on ignition yielded 0.125 g of Pt. What is the molecular formula of the base?
(a) C2H7N (b) C3H9N (c) C7H9N (d) C4H11N
100. 0.5g of the chloroplatinate of organic mono-acid base on ignition gave 0.195g of platinum residue. 0.36g of the base in Kjeldahl’s
experiment liberated 0.136g of NH3. Find the molecular formula of the base if it contains 53.33% C and 15.56% hydrogen.
(At. wt., Pt = 195).
(a) C2H7N (b) C3H9N (c) C7H9N (d) C4H11N
101. Among the following, the optically active compound is:
OH
HNO3
102. HO CHO product. Here product mixture is:
H2O
OH
(a) Optically inactive as it racemic mixture (b) Optically inactive as it is meso
(c) Optically active as it is a single diastereomer (d) Optically active as it is a single enantiomer
103. Identify incorrect statement(s).
Br
Br
Me2CuLi
Me
(a) cis-3,5-dimethylcyclohexanone, which is chiral (b) trans-3,5-dimethylcyclohexanone, which is chiral
(c) cis-3,5-dimethylcyclohexanone, which is achiral (d) trans-3,5-dimethylcyclohexanone, which is achiral
20
The Me-Cha-Nism Mantra PW
105. The [a]D of a 90% optically pure 2-arylpropanoic acid solution is +135°. On treatment with a base at RT for one hour, [a]D changed
to + 120°. The optical purity is reduced to 40% after 3 hours. If so, the optical purity of the solution after 1 hour, and its [a]D after
3 hours, respectively, would be:
(a) 80% and 60° (b) 70% and 40° (c) 80% and 90° (d) 70% and 60°s
OH
OH
(c) OH (d)
O
N
N COCH2CH2N(CH2CH3)2 N N CH2CH2N(CH2CH3)2
O
O
O
(c) CH3 C CH2 CH2 CH O (d) OHC CH CH CHO
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109. Compound ‘W’ is:
CHO
HCHO, | &
COOH
On complete reduction by Na-EtOH, Agathene dicarboxylic acid give hydrocarbon C20H38 which have 5 chiral carbon in it.
113. The structure of Agathene dicarboxylic acid is
(a) (b)
(c) (d)
114. Structure of product formed when Agathene dicarboxylic acid is heated with soda lime is:
22
The Me-Cha-Nism Mantra PW
115. True statement about Agathene dicarboxylic acid is:
(a) it gives red colour with cerric ammonium nitrate (b) it gives red colour with 2,4-dinitrophenyl hydrazine
12 14
(c) it gives off effervescence of CO2 with NaHCO3 (d) none of the above
Comprehension (from Q. 116 to Q. 118)
A compound known as Hagemann’s ester,
can be prepared by treating a mixture of formaldehyde and ethylaceto acetate first with base and then with acid and heat. In the reaction,
first step is an aldol-like condensation.
Second step is Michael addition
Third step is an intramolecular aldol condensation
Fourth step is hydrolysis followed by decarboxylation.
116. Which of the following is Michael addition product?
3 3
3
(a) (b)
3
3 3
3 3
(c) (d) 3
3
3 3
117. Ethylacetoacetate, first treated with base, which is usually ethoxide, on treatment with formaldehyde gives Hagemann’s ester. If
two equivalents of CH3CH2O– will be taken in the beginning, then the first step (of synthesis) product will be.
(a) (b)
(c) (d)
118. If ethylacetoacetate condensation takes place with instead of HCHO, then the methyl substituted Hagemann’s ester is
formed which can be written as
(a) (b)
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Comprehension (from Q.119 to Q.121)
Compound X is a trisaccharide which occurs principally in cotton seed meal. Compound X does not react with Benedict’s or
Fehling’s solutions nor does it mutarotate. Acid catalysed hydrolysis gives three different D-hexoses, A, B and C. Compounds A and B
as well as compound 1 (given below), all give the same osazone upon reaction with excess acidic phenyl hydrazine.
Compound C reacts with nitric acid to give optically inactive compound D. The Kiliani Fischer approach is used to establish the
configurational relationship between D-glyceraldehyde and C. The intermediate aldotetrose which leads to C does not give a meso
compound when oxidised by nitric acid. When A is treated with nitric acid, the dicarboxylic acid (aldaric acid) produced is optically
active. Both A and B reac t with 5 moles of HIO4. One mole of A gives 5 moles methanoic acid and one mole of methanal while one mole
of B gives 3 moles of methanoic acid, 2 moles of methanal and one mole of carbon dioxide. Both A & B are related to the same aldotetrise
which is the diastereomer of the one to which C is related. Methylation of X followed by hydrolysis gives a 2, 3, 4-tri-o-methyl-D-hexose
(E) (derived from A), a 1, 3, 4, 6-tetra-o-methyl-D-hexose (F) (derived from B), and a 2, 3, 4, 6-tetra-o-methyl-D-hexose G (derived
from C).
119. Observe the following molecules
CH2OH
Choose the correct match
(a) A-III, B-V, C-I (b) A-I, B-VI, C-IV (c) A-III, B-IV, C-I (d) A-III, B-V, C-IV
120. How many moles of acetic anhydride are consumed to make A completely acetylated?
(a) 3 (b) 4 (c) 5 (d) 6
121. The trisaccharide ‘X’ is
(a) (b)
(c) (d)
24
The Me-Cha-Nism Mantra PW
Comprehension (from Q.122 to Q.124)
(+) Fenchone is a terpenoid that can be isolated from fennel oil. (±) Fenchone has been synthesized through the following route:
122. In the synthesis, the molecule ‘A’ with the corresponding reaction is
(a) (b)
(c) (d)
125. If product X is treated with AlCl3, it undergoes an intramolecular Friedel-Craft’s reaction. The expected product is
126. If the product of previous question is treated with Br2 in presence of UV-light, it undergoes monobromination to form Z. Z on
treatment with Mg/ether followed by addition of CH2O (methanal) and finally hydrolysis gives an alcohol. This alcohol on treatment
with acid catalyst undergo dehydration to form a highly stable product, what is this product?
25
P 250 + Top most Selected Kattar Advanced Questions
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Comprehension (from Q.127 to Q.128)
A solid compound ‘G’ of formula C15H15ON, was insoluble in water, dilute HCl, as well as dilute NaOH. After prolonged heating
of ‘G’ with aqueous NaOH, a liquid, ‘H’, was observed floating on the surface of the alkaline mixture. ‘H’ did not solidify upon
cooling to room temperature; it was steam-distilled and separated. Acidification of the alkaline mixture with hydrochloric acid
caused precipitation of a white solid, ‘I’. ‘I’ is a paramethyl benzene derivative. Compound ‘H’ was soluble in dilute HCl, and
reacted with benzenesulfonyl chloride and excess KOH to give a base-insoluble solid, ‘J’. Compound ‘I’, m.p. 180oC, was soluble
in aqueous NaHCO3, and contained no nitrogen.
127. Find the number of carbon atoms in ‘I’:
Molecular weight of 'H '
128. What is the value of
53.5
Comprehension (from Q.129 to Q.130)
squalene (S)
129. Find the number of unique products upon ozonolysis of (S).
squalene (S)
(1) O3
(2) Zn/H3O+
Organic products
130. It is given that (S) on reaction with cold dilute alkaline KMnO4 forms P. Treating P with CrO3 in pyridine gives Q. Q with excess
CH3I in alkaline medium gives R. Find the number of carbon atom in R.
CHO
P
NH2
NH2
NH2 NH2
(a) (b) (c) (d)
OH OH
OH OH
132. Which of the following is/are correct statement:
(a) Most favourable site for protonation in (b) The most acidic hydrogen in
(2) NH
(B) (E) 2
N NH2 (1) (3)
(A) HO C CH
H2N (C) is (B)
N is (1)
Me
(4)
N (D) HO
(c) The most acidic hydrogen in (d) Decreasing order of basic strength of the three isomers of nitroaniline
is p-nitroaniline > o-nitro aniline > m-nitroaniline
is (C)
S O O O S S
26
The Me-Cha-Nism Mantra PW
134. Identify the correct product:
CH3 CH3
Cl
Cl Cl D D
(a) (b) D2SO4
Br2 Br C CH2CH2Br
Cl
D
CH2 CH3
(c) H2 (d)
Pd/C
+ HCl
CH3
CH3 Cl
135. Identify the Correct statements:
(a)
2-Methylnapthalene give 2-naphthalenecarboxylic acid on oxidation.
(b)
The trans-isomer of 1, 3-dimethylcyclohexane is more stable because both methyl groups are equatorial.
(c)
While cis-1, 3-di-t-butylcyclohexane exists predominantly in a chair conformation, the trans-isomer adopts a twist conformation.
(d)
Cyclopentane has non-planar ring insprite of the fact that a regular pentagon has internal angles of 108° very close to the
tetrahedral angle.
136. Which among the following cyclic compounds is isolable?
H H H
H
(a) (b) (c) (d) None of these
H H
137. Identify the reactions indicating major products for the following reactions.
HOAc
+ CrO3 H Br
D
Br2
(a) (b)
O
O H Br
O
O
NO2 COCl
AlCl3 O H2SO4
(c) + D
No reaction (d) AlCl3 –H2O
Zn dust
SO3H
H2O
(CH3)2C CHCH2Cl + Ag+ CH3 CH3
HCOOH
(c) (CH3)2CCH CH2 (d) conc. H2SO4
COOH
OH
OH
27
P 250 + Top most Selected Kattar Advanced Questions
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140. Identify correct statements:
(a) (CH3)3CCl reacts faster than (CD3)3CCl in E2 elimination.
(b) II will solvolyze faster than I in SN1 reaction.
CH3 H
H CH3
H Br
Br H
I II
(c) The first order acetolysis (50°C) rate of cyclobutyl p-toluenesulfonate is much lesser than that of cyclopropyl p-toluenesulfonate.
(d) t-Butyl fluoride is solvolyzed only in strong acidic solutions.
141. Identify the correct statements:
(a) The basicity of the following ethers towards BF3 has the following order
H3CO C2H5
OCH3
(A) (B)
(c) The following ketone is usually basic.
O
HO OH C6H5 OH
C6H5 C6H5 HO C6H5
(A) (B)
142. Identify the correct product:
O OH
H+ H+
(a) (b)
O HO
OCH3
OH
Br Br
CH2OH (CH3)2SO4, OH
–
hot KMnO4 Br2
(c)
water
Br
CHO
– H2O/H+ D
(d) CH3COCl CH3COO Na+
D – H2O
OH O O
28
The Me-Cha-Nism Mantra PW
143. Which one of the following carboxylic acids does not undergo decarboxylation easily?
O O
COOH CH3 O
C OH COOH N
(a) (b) (c) O (d) C OH
B Ph
O O
CH 3
144. Which of the following compounds is aromatic?
Br
The reactant ‘X’ can be:
29
P 250 + Top most Selected Kattar Advanced Questions
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150. Which of the following indicates correct feasible products?
O
H
N
MgBr CHO
(i) CH3C N,conc. H2SO4
(a) (ii) H3O+ (b) HC(OC2H5)3 +
OH
O CCl3
O
151. Which of the following are correct statements.
(a) A nitroso (– N O) group activates ortho-and para-positions towards both electrophilic and nucleophilic aromatic substitutions.
(b) Mg can be used in place of Zn in the Reformatsky reaction
(c) Furan has a lower boiling than pyrrole
NH2 C N
(d) has a lesser dipole moment than
N N
O
152. CH3CO3H
(Excess)
Final product of reaction can not be:
O O O
O O HO OH
153. Identify the correct statements:
(a) A is insoluble in water but soluble in dilute sulphuric acid while B is insoluble in both water and dilute acid but soluble in
aqueous solution of strong base.
O O O
NH2 NH2
A B
(b) An alkyne is more reactive than alkene in catalytic hydrogenation reaction while reverse is true for electrophilic addition reaction.
(c) 2,6-di-t-butyl pyridine is more basic the pyridine but later is a stronger nucleophile than former.
(d) Hydrolysis of methyl bromide takes place much faster in presence of NaI.
154. Consider the following six structures:
OH OH OH
H H H
N N N
O O O
I II III
OH OH OH
H H H
N N N
O O O
IV V VI
30
The Me-Cha-Nism Mantra PW
Find the correct match:
H2SO4
(a) + O
Ph
O
(i) NaOH, PhCOCl
OH N
(b) O O O
NH2 (ii)
O Ph O
EtOOC O O
O (i) t-BuOK
OAc (i) MeMgBr
CH3
(c) N (ii) Ac2O (ii) aq NaOH
R CH3
N (iii) Heat N
R R
H
O O
CH3ONa
(d) MeOOC COOMe + O O
heat
O H H
H
156. Identify the correct feasible reactions:
OH O OH HNO2
HNO2
H2SO4
CHO
(a) H2SO4 (b)
NH2 NH2
O O O O
CH3
(c) CH3 NaOMe (d) NaOMe
OH Ph O O
Ph OH Ph Ph
157. Identify the correct feasible reactions:
O OH O
O
H H+ O O
(a) O (b) O
OH HCl
COOEt
O O O
O COOEt
(c) EtO OEt + t-BuOK
(d) EtOOC COOEt
heat Na/excess
HO
COOEt
O EtOOC
158. Identify the correct statements: O
31
P 250 + Top most Selected Kattar Advanced Questions
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159. Identify the correct feasible reactions:
O
NaOH N
(a) OH+ NC N
OMe OMe
H O N
H
O O
m-CPBA CH3COCl/LiCl
(b) A H3C O + H 3C O
Cl
Cl
O O
(c) (i) NaOH/H2O O COOH
(ii) H3O+
O O
(d) BuLi
N OTs +
N
O O
H
(a) Neither pure H2SO4 nor pure HClO4 conduct an electric current.
(b) Cyclopropane is more acidic than propane
(c) Optically active CH3CH2CH(OH)CH3 was found to have lost its optical activity after standing in water containing a few drops
of acid.
(d) Gauche conformation of n-butane is chiral
161. Which of the following are correct statements?
Br
(a) is chiral and possesses a chiral plane
Br
Br
(b) is chiral and possesses a chiral axis
Br
(c) The gauche conformation (q = 60°) of n-butane possesses C2-axis of symmetry; and is chiral
(d) The gauche conformation (q = 60°) of n-butane possesses centre of symmetry; and is achiral
162. Which of the following have gauche conformation most stable?
32
The Me-Cha-Nism Mantra PW
163. Which of the following are correct statements?
(a) Phloroglucinol can behave as an ambident nucleophile but phenol cannot.
(b) Enol-form of 9-formylfluorene is favoured in its equilibrium system
(c) Of the following two compounds, one remains almost exclusively in the enolic form but the other as ketonic form.
(d) The dipole moment of CH2Cl-CH2Cl increases as the temperature is raised
164. In which of the following pair, first species is more stable:
(a) (b)
(b) For the acid-catalyzed hydrolysis of t-butyl-2,4, 6-triphenylbenzoate , in H218O, no 18O is found in the acid.
(c) Deuteration of the methyl group of acetophenone lowers the basicity of the molecule.
33
P 250 + Top most Selected Kattar Advanced Questions
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168. Identify correct statements?
(a) Benzene and hexadeuterobenzene react at the same rate in bromination (HOBr – HClO4)
(b) Benzene and hexadeuterobenzene react at the same rate in sulphonation
(c) 2-methylpyridine is a stronger bronsted base than pyridine towards proton but a weaker lewis base towards trimethylboron
(d) Phenacyl chloride reacts more than 12,000 times as fast as 2-phenylethyl chloride with
KI in acetone
169. Identify correct statements?
(a) Optically active 2-iodooctane undergoes substitution by radioactive iodide ion only half as fast as optical activity is lost.
(b) The azo compound (A) decomposes 20 times faster than (B).
(c) There is no enormous energy barrier against the formation of a bridgehead radical as there is against the formation of a
carbocation.
(c) +NMe3 exhibits only –I effect whereas +PMe3 exhibits both –I and –R effect
(d) FCl and ICl have dipole moment similar in magnitude but in opposite direction
171. Trans-2,3-epoxy butane react with triphenyl phosphine to give
(a) Cis-2,3-epoxy butane (b) Cis-2-butene (c) Trans-2-butene (d) Ph3P=O
172. Identify reactions leading to correct products
Br2/KOH
(a) NH2CONH2 NH2NH2
Br2/KOH
(b) n-C8H17CONH2 n-C8H17CN
OH O
Br2/KOH
(c) C6H5CHCONH2 C6H5CH + NH3
(d)
34
The Me-Cha-Nism Mantra PW
173. Which compound will give the Tollen's test?
(a) (b)
(c) (d)
(c) Maleic anhydride reacts rapidly with 1,3-butadiene, but does not react at all with ethene under thermal conditions
(d) Each of PhCH2COCH2Cl and PhCHClCOCH3 in reaction with NaOMe/MeOH furnishes the same product.
175. Which of the following gives correct product?
C6H5 C6H5
+
(a) C6H5COCH3 H (b)
C6H5
35
P 250 + Top most Selected Kattar Advanced Questions
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178. Which of the following gives correct product?
(a)
OH OH
(c)
(d)
(c) On treatment with aqueous HBr, both cis and trans 2-bromocyclohexanol are converted into the same product.
(d) Pyridine follows nucleophilic substitution easily but not electrophilic.
(a) Has high dipole moment (3.71 D) (b) Follows Reimer-Tiemann reaction
(c) Couples with diazonium ions (d) Follows nitration with dilute HNO3
181. Identify correct statements
(b) Optically active on refluxing in polar solvent like THF or DMF recemizes but it does not occur in cyclohexane.
(c) The addition of Br2 to CH2=CH2 in presence of excess Cl– produces Br–CH2–CH2–Cl as one of the products.
(d) 1,3-Butadiene on reaction with Br–F (mole ratio =1 : 1) gives two products.
182. Identify correct statements
(a) Benzoic acid on reduction with Na in liq NH3 gives 1,2-dihydro product, whereas, anisole gives 2,5-dihydro product.
36
The Me-Cha-Nism Mantra PW
183. Which of the following are correct statements?
(a) 1,3-Butadiene on reaction with Br–F (mole ratio = 1 : 1) produces two products.
(b) Benzoic acid on reduction with Na in liq NH3 gives 1,2-dihydroproduct, whereas, anisole gives 2,5-dihydroproduct.
(c) Electrophilic substitution of pyrrole is difficult than benzene.
(d) Furan undergoes Diels - Alder reaction less readily than pyrrole.
184. Which of the following are correct statements?
(a) Mechanical strength of Nylon is weaker than polyester.
(b) Addition of bromine to ethylene in methanol gives bromomethyl methyl ether as one of the products.
(c) 1-chloromethyl cyclopropane on hydrolysis chiefly gives two products.
(d) 2-methylcyclohexanone gives different enolates under kinetic and thermodynamic conditions.While 2-tetralone gives only
one (same) enolate under kinetic and thermodynamic conditions.
O O
CH3
185. Which of the following reactions gives correct product as shown?
(a)
(b)
(c)
(d)
(a) (b)
(c) (d)
37
P 250 + Top most Selected Kattar Advanced Questions
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188. Which of the following can exhibit conformational isomerism?
(a) CH3Cl (b) CH2= CH2 (c) H2O2 (d) NH2OH
189. Which of the following represent correct products?
(a) (b)
(c) (d)
(b) When cis-3,4-dimethyl-3-hexene is hydrogenated in presence of a Ni catalyst, a meso hydrocarbon is obtained. However,
when trans-3,4-dimethyl-3-hexene is hydrogenated with Ni catalyst, a racemic mixture of products is obtained.
(c) Catalytic hydrogenation of either cis or trans 3,4-dimethyl-3-heptene results in racemic mixture of products.
(d) During light catalyzed chlorination of ethane, some 1-chloro and 2-chloro butane are also produced.
191. Which of the following are correct statements?
(d) Nitroso (–N=O) group activates ortho- and para- positions towards both electrophilic and nucleophilic aromatic substitutions.
192. What is(are) the expected product(s) in free radical chlorination of propane?
(a) Hexane (b) 2-methyl pentane (c) 2,3-dimethyl butane (d) 2,2-dimethyl butane
193. In which of the following reaction, reactants and products are correctly matched?
(a) (b)
(c) (d)
38
The Me-Cha-Nism Mantra PW
195. Identify correct reactions:
(a) (b)
(c) (d)
196. Identify the reactions leading to correct major products in the following reaction
(a) (b)
(c) (d)
197. Identify the reactions leading to correct products in the following reaction
(a) (b)
–
(c) (d)
198. Which of the following reagents is suitable for separating the constituents of given mixture?
(a) Benzoic acid and 2-naphthol: aqueous Na2CO3
(b) Benzoic acid and 2-naphthol: aqueous NaOH
(c) Water-insoluble alcohol and a water-insoluble phenol: aqueous NaOH
(d) Water-insoluble alcohol and a water-insoluble phenol: aqueous Na2CO3
199. Correct statements about Q and R is/are:
OH
Me H3O+
Q
OH
Me
Me
OH H3O+
R
OH
Me
(a) Both Q and R give positive Fehling’s test
(b) Q gives positive iodoform test
(c) R gives positive iodoform test
(d) A bright yellow precipitate is formed when Q and R are treated separately with 2, 4-dinitrophenyl hydrazine.
39
P 250 + Top most Selected Kattar Advanced Questions
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200. Identify the correct statements:
(a) Aniline is sparingly soluble in water and possesses low vapour pressure. It is best purified by steam distillation.
(b) Acetanilide is soluble in boiling water but sparingly soluble in cold water. It is usually purified by crystallization.
(c) Glycerol can be purified by vacuum distillation.
(d) The constituents of a mixture of acetone and methanol can be separated by fractional distillation.
201. Identify the correct statements:
(a) Anthraquinone is prepared by the oxidation of anthracene by chromic acid. The crude reaction product is usually purified by
sublimation.
(b) Chloroform and aniline are easily separated by the technique of azeotropic distillation.
(c) Benzene is added to rectified spirit for its azeotropic distillation to yield absolute alcohol.
(d) Hydrazine does not produce a Prussian blue colour in Lassaigne’s test for the detection of nitrogen.
202. Identify the correct statement(s).
(b) O (i) NaOH, Br2 Here product mixture contains CHBr3 and a chiral acid
(ii) H+
(c) Epoxidation of (R)–cyclohex–2–enol with peracetic acid yields a 95 : 5 mixture of compounds A and B. Compounds A and
B are diastereomers.
Me
Me
(d) is chiral
40
The Me-Cha-Nism Mantra PW
INTEGER TYPE QUESTIONS
204. The number of reducing sugars among the following is________.
OMe OH OH
O O HOH2C O HOH2C O OMe
HO HO OMe
OH OH OH OMe HO OH HO OH
OH OH
CH2OH
HOH2C O OH O
H OH
H OH
HO OH H OH
CH2OH
205. The amount of bromine (atomic wt. = 80) required (in gram) for the estimation of 42.3 g of phenol (molecular wt. = 94 g mol–1)
is ______.
206. Among the following, how many can liberate CO2 on oxidative ozonolysis followed by heat?
(v)
OH
O
xHI
207. CH2 OH
CH2
O CH3
Find the value of x:
O Cl
O O
Cl Cl
O
COCH2CH3
41
P 250 + Top most Selected Kattar Advanced Questions
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210. Find double bond equivalent value of the product obtained by the self condensation of crotonaldehyde, CH3CH CHCHO in the
presence of base.
211. An unknown saturated amine A yields an alkali soluble derivative when reacted with benzenesulfonyl chloride. Compound A on
reaction with nitrous acid gives an alcohol B, which responds to the haloform reaction. Hydrochloride of A contains 37.2% of
chlorine. Find numbers of carbon atoms in A.
212. The substituents R1 and R2 for nine peptides are listed in the table given below. How many of these peptides are positively charged
at pH = 7.0?
H2N—CH—CO—NH—CH—CO—NH—CH—CO—NH—CH—COO–
H R1 R2 H
Peptides R1 R2
I H H
II CH2CH2NHCH3 CH3
III CH2COOH H
IV CH2CONH2 (CH2)4NH2
V CH2CONH2 CH2CONH2
VI (CH2)4NH2 (CH2)4NH2
IX (CH2)4NH2 CH3
213. Find the value of isoelectric pH of (S). The pH at the half-equivalence point of titration of zwitter ion (S), is 9.714 and 2.286 when
separately reacted with NaOH and with HCl respectively.
H3C
CHCH—COOS
H3C Å (S)
NH3
214. In the reaction given below, 4.32g of the compound X was treated with 822 mg of the catalyst Y to yield 2.63g of the product Z.
The mol% of the catalyst Y used in this reaction is ________. (At.Wt : Ru = 101, P = 31, Cl = 35.5) (Put closest value integer
value)
PR3
MeO Cl MeO
+ Ru
Cl Ph
PR3
X Y Z
(R = cyclohexyl)
215. The reaction of 122 g of benzaldehyde with 108 of phenylhydrazine gave 157g of the product.
N
N
H H
The yield of the product is __________%.
42
The Me-Cha-Nism Mantra PW
216. The reaction for the synthesis of benzoic acid via benzonitrile hydrolysis is shown below:
O
N
1. NaOH, H2O OH
2. HCl, H2O + NaCl
A student starts with 2.5 mL of benzonitrile and performs the hydrolysis procedure. She recovers 2.22 g of benzoic acid. Determine
the actual % yield.
217. 12.0 g of acetophenone on reaction with 76.2 g of iodine in the presence of aq. NaOH gave solid A in 75% yield. Approximate
amount (in g) of A obtained in the reaction is: (At. Wt (I) = 127, C = 12, H = 1, O = 16)
218. Reaction of 11.6 g of the aldehyde A with 462 mg of Wilkinson’s catalyst provided 9.2 g of alkene B. Find the sum of mol % of
the catalyst used and the yield of the reaction. (round off to the nearest integer)
CHO
+ (PPh3)3RhCl
+ H NaOH
H 2O +
43
P 250 + Top most Selected Kattar Advanced Questions
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223. Find the number of compounds that DO NOT exhibit optical activity at room temperature.
O
H CH3 CH3 H3COOC H CH3
H C C C C
D Br Ph OCH3 H COOCH3
OH F
H
COOH
HOOC Br
OH
OH OH OCH3
F
Br
224. Among the following compounds, the number of compounds which can exhibit stereoisomerism is_____.
CH3
Br O O
CH3
NH
N O O O
H H
CH3 O H3C CH2
225. Find sum of:
CH3
monochlorination
(i) Number of diastereoisomeric pairs formed in H3C CH3
H3C Cl
Ph
CH3 Cl
(ii) Number of stereoisomers of major product of CH3 alc. KOH (excess)
H
(–2HCl)
CH3 H
CH3 Cl
Ph
44
The Me-Cha-Nism Mantra PW
CH2OH
C O
CHOH 1. NaBH4
(iii) Number of stereoisomers of (P): Product (P).
2. H3O+
CHOH
CHOH
CH2OH
(iv) The number of possible monoalkylated products formed in the Friedel-Crafts reaction of anisole with 2-chloro-3-methylbutane
in the presence of anhydrous AlCl3 at 50°C.
(v) Number of carbonyl groups present in the final product of the following reaction sequence.
O O
O
1. O3, H2O2
O 2. H3O+, D
O
O O
226. Among the following, the number of molecules that possess C2 axis of symmetry is __________ .
Me
Me
Cl Cl
H H
Me
Me
Cl Cl
BF3 CHCl3 2, 5-dimethylthiophene
H H
227. The number of compounds having S-configuration among the following is _________.
H3CH2C CH2CH3
H H H
H OH C C C
H3C Br H3C CH3
CH3
NC H CH3
CH2NH2
H
H3C
228. The ozonolysis reaction of the given compound gives products in the simplest molar ratio x : y. Find the difference of x and y?
229. Dolastatin is an anti cancer compound isolated from Indian sea have Dobabella ausiculasia. One mole of it on acidic hydrolysis
yield how many products (consider only structural isomers)?
H H S
O
H N N N
N N
H
O
CH3 OCH3 O OCH3 O
45
P 250 + Top most Selected Kattar Advanced Questions
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230. The final major product of the following reaction is C.
What is degree of unsaturation of compound C?
231. How many stereoisomers are possible for the following adamantane derivative?
Cl
Br
CH3
CO2H
232. The total number of enolic tautomers possible for I and II together is_____
233. Total number of constitutional isomers possible for trimethyl cyclohexane is____
235. How many different dichlorides, including stereoisomers by Intramolecular Wurtz coupling reaction with etheral solution of sodium,
can give 1, 4-dimethyl cyclohexane?
236. Give number of the products including stereoisomers formed in the following reaction.
237. Find iso-electric point of the given amino acid.
239.
Find value of x.
240. The amount (in grams) of NaOH (MW = 40) required for complete neutralization of one mole of the following compound
is_________.
46
The Me-Cha-Nism Mantra PW
241. The difference between the molar mass of main product and molar mass of starting acid in the reactions of the following unsaturated
acids with bromine as per reaction (i) and (ii) are respectively M1 and M2.
(i) 3-phenylpropenoic acid
(ii) 2-vinylbenzoic acid
Find the value of difference of M1 and M2.
(i) ( A )
2H 2
Pt
→
D.U. of A = x
(ii) The number of products (including stereoisomers) formed in the following reaction = y
(iii) The number of monobrominated products (only structural isomers) obtained in above reaction = z
243. How many pairs of diastereoisomers are possible in the following molecule?
Ph-CH(Cl)CH(Ph)CH(Cl)Ph
244. The difference in DBE of (A) {C40H20O3FCl3Br5I7} and (B) {C20H40O5N18FClBrI} is:
245. Thiamine diphosphate (TPP), a derivative of vitamin B1 required for glucose metabolism, is a weak acid that can be deprotonated
by a base. Find the value of p + q + r + s, where p = sum of total formal charges on the appropriate atoms in both TPP and its
deprotonation product.
q = site of deprotonation
r = total number of lone pairs present in given molecule
s = total number of atoms having lone pair NOT in resonance
246. A tetrapeptide, made up of natural amino acids, has alanine as the N-terminal residue which is coupled to a chiral amino acid.
Upon complete hydrolysis, the tetrapeptide gives glycine, alanine, phenylalanine and leucine. The number of possible sequences
of the tetrapeptide is______.
247. When 0.0088g of a compound (A) was dissolved in 0.5g of camphor, the melting point of camphor was lowered by 8°C. Analysis
of (A) gave 68.18% C and 13.16% H. Compound (A) showed the following reactions.
(i) It reacted with acid chloride and evolved dihydrogen with Na.
(ii) When reacted with HCl + ZnCl2, a dense oily layer separated out immediately.
Compound (A) was passed over Al2O3 at 350°C to give compound (B). (B) on ozonolysis followed by hydrolysis gave two neutral
compounds (C) and (D), which gave positive test with carbonyl reagents but only (C) gave a positive test with Fehling solution
and resinous substance with NaOH. Kf for camphor = 40K kg mol–1. Find sum of molar mass of C and D.
47
P 250 + Top most Selected Kattar Advanced Questions
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248. A monobasic organic acid on analysis gave the following results.
(a) 0.315 g required 33.33 mL of N/10 NaOH for complete neutralisation
(b) 0.2079 g of carius determination gave 0.3157 g silver chloride
(c) 0.189 g gave 0.1761 g CO2 and 0.054g H2O on analysis.
If molecular formula of the compound is CpHqClrOs then find value of p + q - r – s.
249. In the given list, the total number of compounds that form a clear homogenous solution on treatment with cold dilute H2SO4
is __________ .
(i) 1-propyne (ii) cyclohexanone (iii) cyclohexane
(iv) 1-propene (v) propane-1-amine (vi) propoxypropane
(vii) tetrahydropyran (viii) ethyl butanoate (ix) pyridine
250. Find the sum of:
(i) The number of hydrogen bond(s) present in a guanine-cytosine base pair.
(iii) The total number of pair of enantiomers possible with molecular formula C5H2O.
(iv) The number of all possible stereoisomers for the molecule, CH3—CH CH—CH(OH)—CH CH—CH C(CH3)2.
48
The Me-Cha-Nism Mantra PW
ANSWER KEY
11. (b) 12. (c) 13. (a) 14. (b) 15. (b) 16. (d) 17. (c) 18. (a) 19. (c) 20. (b)
21. (a) 22. (c) 23. (a) 24. (c) 25. (b) 26. (b) 27. (c) 28. (c) 29. (a) 30. (c)
31. (c) 32. (d) 33. (a) 34. (a) 35. (a) 36. (d) 37. (c) 38. (d) 39. (b) 40. (d)
41. (a) 42. (c) 43. (b) 44. (d) 45. (a) 46. (b) 47. (c) 48. (a) 49. (a) 50. (c)
51. (c) 52. (d) 53. (a) 54. (c) 55. (c) 56. (b) 57. (b) 58. (a) 59. (d) 60. (c)
61. (d) 62. (b) 63. (b) 64. (c) 65. (a) 66. (c) 67. (c) 68. (c) 69. (b) 70. (d)
71. (b) 72. (a) 73. (c) 74. (a) 75. (b) 76. (a) 77. (b) 78. (c) 79. (b) 80. (d)
81. (d) 82. (c) 83. (c) 84. (c) 85. (d) 86. (c) 87. (c) 88. (c) 89. (a) 90. (b)
91. (b) 92. (c) 93. (a) 94. (d) 95. (a) 96. (c) 97. (c) 98. (a) 99. (c) 100. (a)
101. (d) 102. (b) 103. (b) 104. (b) 105. (a)
116. (c) 117. (b) 118. (b) 119. (a) 120. (c) 121. (a) 122. (c) 123. (c) 124. (d) 125. (a)
126. (c) 127. [8] 128. [2] 129. [3] 130. [36]
136. (b, c) 137. (a, b, c, d) 138. (a, b, c) 139. (a, b, c, d) 140. (a, d)
141. (a, c) 142. (a, b, c, d) 143. (a, c) 144. (a, b, c) 145. (a, c, d)
146. (b, c, d) 147. (a, b, c, d) 148. (b, c, d) 149. (b, c, d) 150. (a, b, c, d)
151. (a, c) 152. (a, c, d) 153. (a, b, c, d) 154. (a, b, d) 155. (a, b, c, d)
156. (a, b, c) 157. (a, b, c, d) 158. (b, c, d) 159. (a, b, c, d) 160. (a, b, c, d)
161. (a, c) 162. (a, b, c, d) 163. (a, b, c, d) 164. (a, c) 165. (a, b, c, d)
166. (a,b,d) 167. (a, b, c, d) 168. (a, c, d) 169. (a, b, c, d) 170. (a, b, c, d)
171. (b, d) 172. (a, b, c, d) 173. (a,b,d) 174. (b, c, d) 175. (a, b, c)
176. (a, c, d) 177. (a, c,d) 178. (a, b, c, d) 179. (a, b, c, d) 180. (a, b, c, d)
181. (a, b, c) 182. (a, b, d) 183. (a, b) 184. (b, d) 185. (a, b, c, d)
186. (a, b, c, d) 187. (c, d) 188. (c, d) 189. (a, b, c, d) 190. (a, b, c, d)
49
P 250 + Top most Selected Kattar Advanced Questions
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191. (a, b,d) 192. (a, b,c) 193. (a, b, c, d) 194. (a, b, c) 195. (a, d)
196. (b, c) 197. (a, c) 198. (a, c) 199. (c, d) 200. (a, b, c, d)
214. [5] 215. [80] 216. [75] 217. [29.55] 218. [91] 219. [60] 220. [62] 221. [80] 222. [4] 223. [10]
224. [10] 225. [25] 226. [7] 227. [4] 228. [1] 229. [6] 230. [6] 231. [2] 232. [6] 233. [6]
234. [5] 235. [7] 236. [6] 237. [3] 238. [6] 239. [2] 240. [160] 241. [81] 242. [2] 243. [5]
244. [15] 245. [25] 246. [4] 247. [102] 248. [2] 249. [4] 250. [18]
50
The Me-Cha-Nism Mantra PW