Advanced Crash Paper

8/12/2019 Advanced Crash Paper

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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

> >


10/15

(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


15/15

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

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