Work sheet on KVPY FIITJEE

Bangalore CENTRE
Subject: CHEMISTRY Topic : Hydrocarbon and GOC Date of Distribution :
NAME: BATCH : Max. Marks :

ONE OR MORE THAN ONE CORRECT TYPE

1. Which of the following preparation method will be better than others in terms of yield of n-butane?

N a , D .E . O
(A) CH3CH2 Br (B) e le c tr o ly s is
CH3CH2
D - +
O Na
( i) M g , D .E . O
(C) CH3CH2CH2CH2 Br (D)
( ii) H 2 O Zn + H3C C OH
CH3CH2 Br
2. In which of the following reactions the major product will have chiral carbon(s)?

D 2 / Ni B r2, h n
(A) CH3CH2 CH2 (B) H3C CH2 CH2 CH3
M o n o b r o m in a t io n
Et O
Z n - C u + E tO H Zn - H g + conc. H C l
(C)
H3C C CH2 Br H3C C CH CH2CH3
(D)
CH2CH2CH3 CH3
3. Among different isomers of pentane; which of the following mentioned properties have been arranged in
correct order ?

(A) n-pentane > iso-pentane> neo-pentane (boiling point)

(B) neo-pentane > n-pentane > iso-pentane (melting point)
(C) n-pentane > iso-pentane > neo-pentane (heat of combustion)
(D) neo-pentane > iso-pentane > neo-pentane (rate of reaction towards Br 2, hn)
4. 1 mole of aqueous solution of sodium acetate is electrolysed completely. What is the total volume of gases
evolves at STP

(A) 22.4 L (B) 44.8 L (C) 67.2 L (D) 33.6 L

1 2
H CH3
H
B r.
5. 3 Relative ease of abstraction of H by Br . follows the order
H
H3C
H3C

(A) 1 > 2 > 3 (B) 2 > 3 > 1 (C) 3 > 1 > 2 (D) 3 > 2 > 1
CH3
B r2; h n F r a c tio n a l
6. H3C X Y fractions ; X & Y respectively are
M o n o b r o m in a tio n isomers d i s t i l l a t i o n
CH3

(A) 8, 5 (B) 8, 8 (C) 8, 4 (D) None of these

7. Which of the following carboxylic acid can be decarboxylated most easily using soda-lime?

O O O O
(A) (B) (C) (D)
C C C C
OH OH OH OH
8. CH3 – CH2 – CH3 can be prepared by

L iA lH 4
( i) M g , D E
(A) H3C CH CH3 (B) H3C CH CH3
Br ( ii) N H 3
Br

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Work sheet Topic : Page 2 of 4

O - O
N 2H + O H R ed P + H I
(C) H3C C CH3
4
(D)
CH3CH2 C H
9. How many dicarbonyls (excludinig stereoisomerism) with molecular formula C 5H8O2 upon reduction with
N2H4 + OH - will form an unbranched alkane with molecular formula C5H12

(A) 6 (B) 7 (C) 8 (D) 9

10. Which of the following alkenes will have heat of hydrogenation more than that of others?

(A) (B) (C) (D) All have same value

11. 0.037 g of an alcohol, R–OH was added to CH 3MgI and the gas evolved measured 11.2 cm 3 at STP. What is
the molecular mass of R–OH ?
(A) 46 (B) 60 (C) 74 (D) 88
12.

(I) (II) (III)

The correct order of reactivity of I, II & III towards addition reactions is :
(A) I > III > II (B) I > II > III (C) III > II > I (D) III > I > II
13. Observe the given compounds and answer the following questions.
C O 2H C O 2H C O 2H C O 2H C O 2H
H O H H O H H O H H O H H O H
H O H H O H H O H H O H H O H
H O H H O H H O H H O H H O H
C O 2H C O 2H C O 2 H C O 2H C O 2H
(I) (II) (III) (IV ) (V )
(i) Which of the above formulae represent identical compounds?
(a) I and II (b) I and IV (c) II and IV (d) III and IV

(ii) Which of the above compounds are enantiomers?

(a) II and III (b) III and IV (c) III and V (d) I and V

14. What observed rotation is expected when a 1.5 M solution of (R)-2-butanol is mixed with an equal volume of a
0.75 M solution of racemic 2-butanol and the resulting solution is analysed in a sample container that is 1 dm
long? The specific rotation of (R)-2-butanol is -13.9 0 ml gm–1 dm–1.
(a) +0.770 (b) – 0.770 (c) +0.350 (d) – 0.350

15. A pure sample of 2-chloro butane shows rotation of PPL by 300 in standard conditions. When above sample is
made impure by mixing its opposite form, so that the composition of the mixture becomes 87.5% d-form and
12.5% l-form, then what will be observed rotation for the mixture
(a) -22.50 (b) +22.50 (c) +7.50 (d) -7.50
16. Isomers which can be interconverted through rotation around a single bond are
(a) Conformers (b) Diastereomers (c) Enantiomers (d) Positional isomers

H 3C H
C == C H
17. The H 3C C shows
CO O H
CH 3
(a) Geometrical isomerism (b) Optical isomerism
(c) Geometrical and optical isomerism (d) Tautomerism

18. How many optically active stereoisomers are possible for butane-2, 3-diol?
(a) 1 (b) 2 (c) 3 (d) 4

19. The number of possible enantiomeric pairs that can be produced during monochlorination of
2-methyl butane is
(a) 2 (b) 3 (c) 4 (d) 1
20. When cyclohexane is poured on water, it floats, because

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(a) Cyclohexane is in ‘boat’ form (b) Cyclohexane is in ‘chair’ form

(c) Cyclohexane is in ‘crown’ form (d) Cyclohexane is less dense than water

21. Which of the following compounds will show geometrical isomerism?

(a) 2-butene (b) propene (c) 1-phenylpropene (d) 2-methyl-2-butene

22. Which of the following compound will exhibit geometrical isomerism?

(a) 1-Phenyl-2-butene (b) 3-Phenyl-1-butene
(c) 2-Phenyl-1-butene (d) 2-methyl-2-butene

23. The number of isomers for the compound with molecular formula C 2BrClFI is
(a) 3 (b) 4 (c) 5 (d) 6

24. Which of the following compounds exhibits optical isomerism?

(a) 2-methylbutene-1 (b) 3-methylbutyne-1
(c) 3-methylbutanoic acid (d) 2-methylbutanoic acid
4
25. In the given conformation, if C2 is rotated about C2—C3 bond anticlockwise by an angle of CH 3
1200 then the conformation obtained is H H
(a) Fully eclipsed conformation
(b) Partially eclipsed conformation
3
(c) Gauche conformation 2
(d) Staggered conformation
26. On monochlorination of 2-methylbutane, the total number of chiral compounds formed is H H
(a) 2 (b) 4 (c) 6 (d) 8 1 CH 3

27. The number of structural isomers for C6H14 is

(a) 3 (b) 4 (c) 5 (d) 6

28. Statement-1 : Molecules that are not superimposable on their mirror images are chiral.
Because
Statement-2 : All chiral molecules have chiral contres.
(a)Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
(b) Statement-1 is True; Statement-2 is True; Statement-2 is not correct explanation for Statement-1
(c) Statement-1 is True, Statement-2 is False
(d) Statement-1 is False, Statement-2 is True.
29. The correct statement(s) concerning the structures E, F and G is(are)
O O H H 3C CH 3
H C3
H 3C

H 3C CH 3 H 3C CH 3 H 3C O H
(E ) (F ) (G )
(a) E, F and G are resonance structures (b) E, F and E, G are tautomers
(c) F and G are geometrical isomers (d) F and G are diastereomers

SUBJECTIVE

30. Write structural formulae for all the isomeric alcohols having the molecular formula C 4H10O. (4)
31. Identify the pairs of enantiomers and diastereomers from the following compound I, II and III.
CH 3 CH 3 CH 3

H O H O H H O H H
O H H O H H H O H
CH 3 CH 3 CH 3
(I) (II) (III)
(Enantiomers-I and III; diastereomers-I & II and II & III )
32. What are the relationship between the following pairs of isomers?

Br C O 2H Br C O 2H Br Br
(A) (B) Br Br
and and

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CH O CH O
CH O C H 2O H
H O H H O H
H N H 2 H O H
(C) H O H and H O H (D) H O H and H N H
H O H H O H 2

C H 2O H CH O
C H 2O H C H 2O H
H C l
H H H CH 3

(E) and (F) and

C l Ph H Ph
CH 3 H
(A) Geometrical isomers & Diastereomers (B) Positional (C) Optical (Diastereomers)
(D) Diastereomers (E) Enantiomers (F) Geometrical isomers (Diastereomers)

33. Calculate the total number of geometrical isomers possible for

H C H =C H –C H 3
(A) (B) C == C == C
Cl C H =C H –C H 3

(A) 16 (B) 4
34. With reasons, state whether each of the following compounds I to IX is chiral.
Cl C l

(I) H (II) H (III)

Cl H
H O 2C C O 2H
H C l
Ph

Cl C O 2H O O M e
(IV) C == C == C (V) (VI) (VII) S == O
Cl M e Ph
C O 2H
achiral : I, III, IV ; chiral : II, V, VI, VII

Comprehension
For the given question (1, 2, 3) consider the following reaction .
CH3

light monohalogenation product

X2

35. Light is involved in which step of the reaction :

(A) Initiation only (B) Termination only
(C) Propagation only (D) Propagation and Termination

36. Which halogen will give the best yield of a single monohalogenation product ?
(A) F2 (B) Cl2 (C) Br2 (D) I2
37. How many monohalo derivatives are possible (excluding stereoisomes) ?
(A) 3 (B) 4 (C) 5 (D) 6

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