advanced crash paper
TRANSCRIPT
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ADVANCED CRASH COURSE
SINGLE CORRECT
1. Which of the following pairs is homologue?
(a) 3 3 3CH OH, CH O CH (b) 3 3CH OH,CH SH
(c) 3 3 3 2CH O CH , CH CH OH (d) 3 3 2CH OH, CH CH OH
2. Which of the following name will be incorrect?
(a) (b)
(c) (d)
3.
True statement for the above compounds is:
(a) (i) is phenol while (ii) is alcohol
(b) Both (i) and (ii) are primary alcohol
(c) (i) is primary and (ii) is secondary alcohol
(d) (i) is secondary and (ii) is primary alcohol
4.
(a) Chain isomer (b) Positional isomer (c) Functional isomer (d) Metamers
5.
(a) (b) (c) (d)
6. How many geometrical isomers are possible for :
(a) 0 (b) 1 (c) 2 (d) 3
3, 6 Dimethyl cyclohexene 1, 6- Dimethyl cyclohexene
6, 6-Dimethyl cyclohexene1, 5-Dimethyl cylohexene
OH CH2CH2OHand
(i) (ii)
3 2 2 2CH CH CH CO H 3 3CH CH CH ; A and B are :
2CO H
(A)
(B)
NH
O
(A)
KOH(B) Tautomer (B) is:
N
OH
N
H
OH
N
OH
N
OH
ClCl
Cl
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7. What is the relationship between the following compounds?
(a) enantiomers (b) diastereomers
(c) constitutional isomers (d) conformational isomers
8. Which of the following is a meso compound?
(a) (b) (c) (d)
9.
Arrange the following in deceasing order of bond energy:
(a) Ha>Hc>Hb (b) Ha>Hb>Hc (c) Hb>Ha>Hc (d) Hb> Hc > Ha
10. Which of the following is not a resonance structure of the others?
(a) (b) (c) (d)
11.
Which of the following orders of rotation barrier about the C = C bond, as indicated, is correct
(a) I > II > III (b) III > II > I (c) III > I > II (d) II > I > III
12.
3CH
Cl
H
H
Cl
3CH
3CH
3CH
H
HCl
Cl
and
3CH
Cl
H
H
Cl
3CH
3CH
3CH
H
HCl
Cl
3CH
Cl
H
H
Cl
2 3CH CH
3CH
H
HCl
Cl
2 3CH CH
CH3
Hc
Hb
Ha
O O O O
CH=CH 2 CH CH
CH CH OCH 3
=
(I) (II)
(III)
=
2CH OH 2CH OH
2CH OH
H
HO
OH
CHO
H
HO
HO
H
H
H
H
CHO
OH
OHCHO
(a) (b) (c)
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D and L configuration of above carbohydrate is
(a) L, L, D (b) L, D, L (c) L, L, L (d) L, D, D
13. Compare heat of combustion :
(i) (ii) (iii)
(a) i > ii > iii (b) ii > i > iii (c) iii > i > ii (d) ii > iii > i
14. What is the major product of the following reaction?
(I) (II) (III)
(IV) (V)
(a) I (b) II (c) III (d) IV
15. Which of the following product is not formed in the following reaction?
(a) (b) (c) (d)
H B ; A & B
are isomers ; Isomer (B) is :16.
(a) (b)
(c) (d)
o2
NBS alc. KOH HCHO,H
H O500 C A B C;
End product (C) of reaction will be:17.
CH3
2H O
H Major Product
CH2OH CH3
OH
CH3
OH
CH3
OH
CH3
OH
HBr
BrBr Br
Br
OOCHO
(A)
2CH
OH
O
OH
O
OO
O
O
O
OH OH
2CH
H O
O
CH2- CH 3
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O
3 2CH CH
3CH
2H C CH
O
O
(a) (b)
(c) (d)
18. Arrange the following carbonyl compounds in decreasing order of their reactivity in nucleophilic
addition reaction.
(a) ii > iii > i > iv (b) ii > i > iv > iii (c) iii > ii > i > iv (d) iii > i > iv > ii
19. Which of the following compound show iodoform test?
(b) 3 2 3CH CO CH CO CH (a)
(c) (d)
20.
(a) (b) (c) (d)
21. Which of the following reactant on reaction with conc. NaOH followed by acidification gives the
following lactone as the product?
(a) (b) (c) (d)
2 2Ph CH CH CH OH
OH
3Ph CH CH CH
OH OH
2 3Ph C CH CH
O
2 3Ph CH C CH
O
CHO
NO2
CHO COCH 3
CH3
CHO
(i) (ii) (iii) (iv)
H
2 3 3CH C C CH D
O
OH
O O
3C CH
O
CHO
C - OCH 3
CO2H
OCO2H
CHO
CHO
CHO
CO2H
CO2H
3OH HOZn72%
A B C ; Pr oduct C is :
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22. Which keto acid shown will not undergo decarboxylation?
(a) (b) (c) (d)
23. An optically active compound X has molecular formula 4 8 3C H O . It evolves 2CO with 3NaHCO .
X reacts with 4LiAlH to give an achiral compound. X; is :
(a) (b)
(c) (d)
3H O / A ;
product (A) of the reaction is :24.
(a) (b)
(c) (d)
25. 3 2 2CH CH CH CH CO H X Product (X) is:
(a) 3 2 5CH CH CH C H (b)
(c) 3 2 2CH CH CH CH (d) 3 2CH CH CH
26. Predict the major product P in the following reaction.
(a) (b)
O
CO2H
O
CO2H
2 2Ph C CH CO H
O
3 2 2CH C CH CO H
O
OH
3 2CH CH CHCOOH 3CH CHCOOH
Me
3CH CHCOOH
2CH OH
OH
3 2CH CHCH COOH
CN
CN
CN
CN
O
O
O
O
O
O
CO2H
CO2HO
O
O
3 2CH C CH
3CH
OH
2
NH
Me
Me
Me
2HNO P
Me
Me
MeO
OHMe
Me
Me
OH Me
Me 2CH
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(c) (d)
27. Which amine yields N-nitroso amine after treatment with
acid ( 2NaNO , HCl )?nitrous
(a) (b) (c)
(d)
28. Among the given pairs, in which pair second compound less enol content than first compound?
(a) (b) (c) (d) None of these
29. Which of the following have plane of symmetry
(a) (b) (c) (d) All of these
30. Which of the following does not form a stable hydrate on addition of 2H O
(a) (b) (c)
(d)
31. Increasing order of rate of reaction with 3 2 4HNO H SO is
(a) III < II < I (b) II < III < I (c) I < III < II (d) I < II < III
32.
Major product of the reaction is
(a) (b) (c) (d)
OH Me
Me
Me
CH2NH2NH2CH3 N NHCH 3
3CH
3CH
Ph H
BrPh 2Alc.KOH
E elemination (Major Product)
O O
O
O O
O
HH
H
H
HH
H
H
H
H
H
H
Ph C C C Ph
O O O
O
O
O
O O
O
O
O
O
OOO
O
OO OO
(I) (II) (III)
Ph
C = C
Ph 3CH
3CH Ph
C = C
Ph
3CH3CH Ph
C = C
Ph
3CH
3CH Ph CH CH Ph
3CH OH
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MULTIPLE QUESTIONS
33. Which of the following statements is/are not correct?
(A) A compound whose molecule has D configuration will always be dextrorotatory
(b) A compound whose molecule has D configuration may be dextrorotatory or levorotatory
(c) A compound whose molecule has L configuration will always be levorotatory
(d) A compound whose molecule has L configuration may be dextrorotatory or levorotatory
34. An unsaturated hydrocarbon on complete hydrogenation gives 1-isopropyl-3 methylcyclohexane
after ozonolysis it gives one mole of formaldehyde one mole of acetone and one mole of 2,4-
Dioxohexanedial. The possible structure/s of the hydrocarbon may be
(a) (b) (c) (d)
35. Which of the following statement/s is/are true about the following compounds
(a) (I) and (III) are identical (c) (I) and (III) are geometrical diastereomers
(b) (I) and (II) are structural isomers. (d) (II) and (III) are structural isomers.
36. Which of the following are pair of antiaromatic species.
(a) (b) (c) (d)
37. Identify the non aromatic species (more than one correct)
(a) (b) (c) (d)
38. Which of the following reactions give alkylation product:
(a) (b)
(c) (d)
39. The ether when treated with conc. HI produces
(a) (b) (c) (d)
40. The following conversion reaction can be carried out by using reaction sequence/s.
(a) 32 H O ,Br /FeZn / Hg / HCl, KCN
(b)
(c) (d) 3NaHCO
B
H
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41. Consider the following reaction
P & Q will be
(a) (b) (c) (d)
42. Which of the following compounds are polar
(a) (b) (c) (d)
43. Which of the following compounds are aromatic
(a) (b) (c) (d)
44. Which of the following reaction give aromatic ions
(a) (b) (c) (d)
45. A hydrocarbon 'P'(C9H10) on bromination with Br2/Fe produces Q(C9H9Br). P on KMnO4/OH-
oxidation forms R (C8H6O4) which on further heating produces S(C8H4O3). The compound 'P'
and R can be
(d) R is(a) P is (b) R is (c) P is
46. Compound 'P' (C10H12O) evolves H2with Na metal. It reacts with Br2/CCl4to give 'Q'
(Cl0H12Br2O).With I2/NaOH it forms iodoform and an acid 'R' (C9H8O2). 'P' has geometrical and
optical isomers. The structure of 'P' and 'R' should be
(a) (b) PH-CH = CH-COOH (c) (d)
47. Which of the following ion will be aromatic in nature?
(a) (b) (c) (d)
48. Select the reactions in which the correct orientations have been mentioned in the major products.
(Products)
(Products)
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(a)
(b)
(c)
(d)
49. What is true about the following reactions
(a) I is aromatic (b) II is aromatic
(c) III is antiaromatic (d) Out of I, II and III only one compound is nonaromatic
50. Which of the following compounds will react with 3NaHCO solution to give sodium salt and 2CO
(c) 3CH .COOH (d)(a) (b)
51. Which of following compound are stronger base then acetamide.
(c) 2Ph.CONH (d)(a) (b)
52. Which of the following are correct acidic strength order
(a)
(b)
OH
NO 2
NO 2
NO 2
OH SO3H
2NH
C NH2NH
=
3CH
C NH2NH
= NH2
I
COOH
I > Br
COOH
Br>
Br
COOH
COOH
NO2
COOH
NO2NO2
COOH
> >
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(c)
(d)2 3 3
H CO CH CH NH
COMPREHENSION TYPE:
PASSAGE 1 :An alcohol P, which gives positive iodoform test, undergoes
reaction with 2 molecules of PCC (pyridinium chloro chromate) gives
compound Q. compound Q on reaction with dil. KOH followed by
heating gives compound R. Ozonolysis of R leads to a tricarbonyl
compound S, which on reaction with4
LiAlH gives compound T the
structure of compound T will be
3 4
2
i OH i O LiAlH2 moles of PCC
ii ii Zn, H OP Q R S T
53. The structure of the carbonyl compound Q is:
(a) (b) (c) (d)
54. The structure of the carbonyl compound R is:
(a) (b) (c) (d)
55. The structure of the carbonyl compound S is:
(a) (b) (c) (d)
PASSAGE 2 :
A compound (A) gives positive test with 2 4Br /CCl . When (A) undergoes reductive
ozonolysis product (B) is obtained. When (B) reacts with dil. KOH followed by heating (C) will obtained
(C) gives positive Tollens test. When (C) reacts with 2 2NH NH / KOH / Product (D) will obtained.
(D) =
2CH OH
2CH OH
O
(T)
OH
O
H
O
O
H
O
O
O
O
H
H
OHO
OH
O O O
O
O
CHO
H
O
O
O
O
O
OH
O
O
O
2 5C H
3CH
CH3
COOH
CH3CH3
NO 2
COOH
CH3
NO2
CH3 NO2
COOH
> >
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56. Compound (A) is :
(a) (b) (c) (d)
57. Compound (B) is :
(a) (b) (c) (d)
O CH CH O
58. Compound (C) is :
(a) (b) (c) (d)
PASSAGE 3:
32 CHClBr3 KOH KOHA NH B C D
Compound (D) is
59. Compound (A) is:
(a) (b) (c) (d)
60. Compound (B) is :
(a) (b) (c) (d)
61. Compound (C) is :
(a) (b) (c) (d)
Passage 4 :
The halogens, 2Br and 2Cl , and add to alkanes. When the electrons of the alkene approach a
molecule of 2Br or 2Cl , one of the halogens atoms accepts them and releases the shared electrons to the
other halogen atom. Therefore, inan electrophilic addition reaction,
2Br behaves as if it were Br ,
CH2
CHO
CH2- CH2- CH=O
CH2-CHO
CH2- CHO
O
CHO
CHO
O
CHO
N= C
2NH C N
OH
NH2
OH
O
O
2NH
CH2-NH2
N
H
CH2-NH2 NH2
N
H
NH-CH 3
Br
2 2 2 2 2 21,2 dibromoethanea vicinaldibromide
H C CH Br Br H C CH B r BrCH CH Br
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and 2Cl behaves as if it were Cl and Cl .
62. cis-2-butene 24
Br
CCl
How many products will obtained in this reaction?
(a) 1 (b) 2 (c) 3 (d) 4
63. I Br3 2CH CH CH Product (A) is :
(a) (b) (c) (d)
64. What are the products from following reaction?
(a) I & II (b) I & III (c) I & IV (d) II & III
MATRIX MATCH
65. Match the column I and II. [(Matrix)]
Column (I) Column (II)
Reactant Product
(a)O
H
excess
PhMgBr Cl C O Et
(p)2Ph CH OH
(b)O
H
excess
PhMgBr H C O Et
(q)OH
Ph CH Ph
(c)O
H
excess
PhMgBr H C H
(r)OH
Ph C Ph
Ph
Br
II
I
Br
I
Br
Br
2 4Br /CCl ?
Br
BrBr
Br
BrBrBr Br
(I) (II) (III) (IV)
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(d) O
3 H
excess
PhMgBr CH C O Et
(s) OH
Ph C Ph
3CH 66.
Column (I) Column (II)Reactant Product
(a)
CH3
3
3 2
1 BD :THF
2 CH CO T
(p)
CH3D
T
(b)
CH3
3
3 2
1 BT :THF
2 CH CO T
(q)
CH 3D
CH3
3
3 2
1 BD :THF
2 C H C O H
CH3
D
(d) CH3
3
3 2
1 BH :THF
2 CH CO D
(s) CH3T
T
INTEGERS
67. How many benzylic hydrogens are present in following compound
68. How many structural isomers are possible for following compound when one hydrogen is replaced
by a chlorine atom
69.
CH2
Reaction - 1: 5 23
PCl 1. NaNH
3 32. CH IPh C CH Ph C C CH
x
O
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70. (a)
(b)
(c)
(d)
Sum of X + Y + Z + P =
71. xis total number of HEM (Hoffman Exhaustive Methylation) to remove nitrogen
from given compound.
yis total number of possible 2E product (including stereoisomer)
Sum of x + y = ?
72. (including stereoisomer)
Total number of products are:
73.
How many dichloro products are formed in the above reaction (including stereoisomers)?
74. How many different Grignard reagents when react with EtOH, give n-butane as product
(excluding stereoisomerism).
75. (x). Find (x) total number of di-chloro products.
S-2-chloro hexane
Reaction - 2: 2NaNH3 3
CH C C CH y
Br
BrReaction - 3: 2NaNH Et I Ph C C Et
z
2Ph CH CH
Cl Cl alc.KOH X productsBr
alc.KOH YBr
alc.KOH Z
Br
alc.KOH P
Br
H3CH
3CH
3CH
N
Br
alc.KOH
3 3CH CH CH CH
3CH
Br 1EtOH 1N
consider all products
x S E
2Cl excess /hv
2 2 2 3CH CH CH CH
H Cl
3CH
2Cl
hv
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76. How many distinct monochlorinated products, (including stereoisomers) may be obtained when the
alkane shown below is heated in the presence of 2Cl ?
77. How many distinct monochlorinated products, (including stereoisomers) may be obtained when the
alkane shown below is heated in the presence of 2Cl ?
ANSWER KEY
1. d 2. c 3. d 4. a 5. a 6. c 7.
a
8. a 9. d 10. d 11. a 12. b 13. b 14. c
15. d 16. b 17. a 18. b 19. b 20. c 21. c
22. b 23. c 24. d 25. c 26. a 27. d 28. C
29. d 30. d 31. d 32. c 33. a,c 34. a,c 35. b,c,d
36. b, d 37. a,d 38. a,b,d 39. a,d 40. b, c 41. c,d 42. b,c,d
43. a,b,c,d 44. b,c,d 45. a,b 46. b,c 47. a,c 48. a,c 49. a,b,d
50. a,c,d 51. a,b,c,d 52. c,d 53. b 54. c 55. a 56. b
57. a 58. a 59. d 60. b 61. b 62. b 63. a
64. a 65. ar; bq; cp; ds 66. ap; bs, cq; d - r
67. 5 68. 4 69. 8 70. 8 71. 6 72. 6 73. 7
74. 2 75. 9 76. 1 77. 8