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Advanced Practice Test Isomerism ACEG

1. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are:

(A) chain isomers (B) geometrical isomers
(C) metamers (D) conformational isomers
2. Molecular formula C5H10O can have :
(A) 6-Aldehyde, 4-Ketone (B) 5-Aldehyde, 3-Ketone
(C) 4-Aldehyde, 3-Ketone (D) 5-Aldehyde, 2-Ketone
3. The number of primary, secondary and tertiary amines possible with the molecular formula C3H9N respectively:
(A) 1, 2, 2 (B) 1, 2, 1 (C) 2, 1, 1 (D) 3, 0, 1
4. C7H7Cl shows how many benzenoid aromatic isomers?
(A) 4 (B) 3 (C) 5 (D) 6
5. Molecular formula C3H6Br2 can have:
(A) Two gem dibromide (B) One vic dibromide
(C) Two ter.- dibromo alkane (D) Two sec.-dibromo alkane

Br COOH COOH Br

6. and are:

HOOC Br Br COOH
(A) Positional (B) Chain (C) Geometrical (D) Functional
7. Which of the following has incorrect relation:
Me
Pr Pr
(A) & identical
Me

Me Et
(B) & positional isomers
Pr Pr
Et Et
(C) & positional isomers
Pr
Pr
Me
Me
Et
(D) & homologues
Pr

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COOH
OCOH
8. & functional isomer

OMe OEt
Et
& metamers
Me
CH2 – CH2 – OH CH2 – O – CH3

& metamers

Me – N – Me CH2 – NH – CH3

& functional isomers

(A) TFTF (B) FTTF (C) TTFT (D) TFFT

O O
Cl C—O C—O Cl
9. H and CH3
C=C C=C
H CH3 H H
Shows which type of isomerism:
(A) Functional group isomerism (B) Geometrical isomerism
(C) Metamerism (D) Position isomerism
10. The type of isomerism observed in urea molecule is:
(A) Chain (B) Position (C) Geometrical (D) Functional
11. How many minimum no. of C-atoms are required for position & geometrical isomerism in alkene?
(A) 4, 3 (B) 4, 4 (C) 3, 4 (D) 3, 3
12. How many structural formula are possible when one of the hydrogen is replaced by a chlorine atom in anthracene?
(A) 3 (B) 7 (C) 4 (D) 6
13. Which of the following cannot be written in an isomeric form?
(A) CH3– CH(OH)–CH2–CH3 (B) CH3– CHO
(C) CH2= CH–Cl (D) Cl – CH2CH2 – Cl
14. Only two isomeric monochloro derivatives are possible for (excluding stereo)
(A) n-butane (B) 2, 2-dimethylpentane
(C) benzene (D) neopentane
15. Given compound shows which type of isomerism:
O O
S—O and S—O
O O
(A) Chain isomerism (B) Positional isomerism
(C) Metamerism (D) Functional group isomerism

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16. Which of the following is not the correct relationship:

Me Me Me
Me Me

Me Me
O – Me O–Me
OH OH
I II III IV
(A) II & IV are metamer (B) I & II are functional isomer
(C) I & III are chain isomer (D) I and IV are positional isomer
17. Which of the following does not show geometrical isomerism?
(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1, 4-dichloro-2-pentene
18. What characteristic is the best common to both cis-2-butene and trans-2-butene?
(A) B.P. (B) Dipole moment
(C) heat of hydrogenation (D) Product of hydrogenation
19. The number of cis-trans isomer possible for the following compound:

(A) 2 (B) 4 (C) 6 (D) 8

20. Which of the following have zero dipole moment?
(A) benzene 1,4- diol (B) trans-1,2-dichloro ethene
(C) cis-1,2-dichloro ethene (D) 1,1-dichloro ethene
21. Which of the following will not show geometrical isomerism:

Me Me
(A) (B) (C) Cl (D)
Me

22. Geometrical isomerism is possible in:

(A) isobutene (B) acetone oxime
(C) acetophenone oxime (D) benzophenone oxime
23. The number of isomers of C5H10 is:
(A) 10 (B) 11 (C) 12 (D) 13
24. Which of the following have asymmetric carbon atom?

C l Br H Cl H Cl H H
| | | | | | | |
(A) H  C  C H (B) H  C  C  Cl (C) H  C  C H (D) H  C  C  CH 3
| | | | | | | |
H H H H H H Br OH
25. The number of isomers of dibromoderivative of an alkene (molar mass 186 g mol–1) is:
(A) 2 (B) 3 (C) 4 (D) 6

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26. Meso-tartaric acid and d-tartaric acid are:

(A) positional isomers (B) enantiomers
(C) diastereomers (D) racemic mixture

27. The number of isomers of C3H5Br3 is:

(A) 4 (B) 5 (C) 6 (D) 7

28. The number of optically active compounds in the isomers of C4H9Br is:
(A) 1 (B) 2 (C) 3 (D) 4

29.

The compound with the above configuration is called:

(A) (2S, 3S)-2-chloro-3-pentanol (B) (2S, 3R)-2-chloro-3-pentanol
(C) (2R, 3R)-2-chloro-3-pentanol (D) (2R, 3S)-2-chloro-3-pentanol

30. The full name of the compound is:

(A) (2R,3R)-3-chloro-2-pentanol (B) (2R,3S)-3-chloro-2-pentanol

(C) (2S,3R)-3-chloro-2-pentanol (D) (2S,3S)-3-chloro-2-pentanol
31. The structure of (2R, 3R)C2H5CH(CH3)CH(D)CH2D is:

(A) (B) (C) (D)

32. The structure of (2R, 3S)C2H5CH(CH3)CH(D)CH2D is:

(A) (B) (C) (D)

33. How many stereoisomers can exist for the following acid
H  C(OH).CO 2 H
|
H  C.CO 2 H
|
H  C(OH).CO 2 H
(A) Two (B) Four (C) Eight (D) Sixteen

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34. How many stereoisomers of the following molecule are possible?

HOOC.CH=C=CH.COOH
(A) two optical isomers (B) two geometrical isomers
(C) two optical and two geometrical isomers (D) None of these

35. The structures shown here are related as being:

(I) (II)
(A) confermers (B) enantiomers
(C) geometrical isomers (D) diastereoisomers
36. Observe the given compounds and answer the following questions:

(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
37. Which species exhibits a plane of symmetry?

(A) (B)

(C) (D)

38. Increasing order of stability among the three main conformation (i.e. eclipse, anti, gauche) of ethylene glycol is:
(A) Eclipse, gauche, anti (B) Gauche, eclipse, anti
(C) Eclipse, anti, gauche (D) Anti, gauche, eclipse
39. How many primary amines are possible for the formula C4H11N?
(A) 2 (B) 3 (C) 4 (D) 5

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40. Number of possible 3D-isomers of glucose are:

(A) 10 (B) 14 (C) 16 (D) 20
41. The total number of isomeric optically active monochloro isopentane is:
(A) two (B) three (C) four (D) one
42. On chlorination of propane number of products of the formula C3H6Cl2 is:
(A) 3 (B) 4 (C) 5 (D) 6
43. The number of optically active isomers observed in 2,3-dichlorobutane is:
(A) 0 (B) 2 (C) 3 (D) 4
44. 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°ml gm–1dm–1:
(A) +0.77° (B) –0.77° (C) +0.35° (D) –0.35°
45. The two compounds given below are:

(A) enantiomers (B) identical (C) optically inactive(D) diastereomers

46. A pure sample of 2-chlorobutane shows rotation of PPL by 30° 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 the observed rotation for the mixture:
(A) –22.5° (B) +22.5° (C) +7.5° (D) –7.5°
47. When an optically active compound is placed in a 10 dm tube is present 20 gm in a 200 ml solution rotates the
PPL by 30°. Calculate the angle of rotation & specific angle of rotation if above solution is diluted to 1 Litre:
(A) 16° & 36° (B) 6° & 30° (C) 3° & 30° (D) 6° & 36°
48. Which of the following will not show optical isomerism:
(A) Cl–CH=C=C=CH–Cl (B) Cl–CH=C=C=C=CH–Cl

(C) (D)

49. The R/S configuration of these compounds are respectively:

HO H
CF3 H NH2 H CH3
HS CHO
COOH

(A) R,R,R (B) R,S,R (C) R,S,S (D) S,S,S

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50. Which of the following combinations amongst the four Fischer projections represents the same absolute
configurations?

(A) (II) and (III) (B) (I) and (IV) (C) (II) and (IV) (D) (III) and (IV)

ANSWER KEY LEVEL - 1

1.(C) 2.(B) 3.(C) 4.(A) 5.(A) 6.(A) 7.(B) 8.(C) 9.(C) 10.(D)

11.(B) 12.(A) 13.(C) 14.(A) 15.(C) 16.(D) 17.(C) 18.(D) 19.(A) 20.(B)

21.(A) 22.(C) 23.(D) 24.(D) 25.(B) 26.(C) 27.(C) 28.(B) 29.(A) 30.(A)

31.(A) 32.(B) 33.(B) 34.(A) 35.(D) 36.(i - B ; ii - C)37.(D)38.(C) 39.(D) 40.(C)

41.(C) 42.(C) 43.(B) 44.(B) 45.(A) 46.(B) 47.(B) 48.(A) 49.(A) 50.(C)

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