02 Isomerism
02 Isomerism
6. Which of the following molecular formula does not (1) 1–Butanol (2) 2–Butanol
show chain isomerism :- (3) 2–Methoxy propane (4) 1–Propanol
(1) C4H10 (2) C4H8 (3) C4H6 (4) C4H8O
13. How many isomeric pentynes (C5H8) are possible
7. The minimum number of carbon atoms present (1) 3 (2) 4
in an organic compound to be able to show position
(3) 5 (4) 6
isomerism is
(1) 3 (2) 4 (3) 2 (4) 5 14. Isomerism exhibited by acetic acid and methyl
formate is :
8. Alkenes with the molecular formula C4H8 do not
show :- (1) Functional (2) Chain
(1) Chain isomerism (3) Geometrical (4) Optical
(2) Geometrical isomerism
15. The total number of aldehydes and ketones with
(3) Position isomerism
the molecular formula C4H8O is -
(4) Optical isomerism
(1) 2 (2) 3
(3) 4 (4) 5
23. Geometrical isomers are differ in :–
16. Urea H2N–C–NH2 molecule exhibits (isomerism):- (1) Position of functional group
O
(2) Position of atoms
(1) Chain (2) Position (3) Spatial arrangement of atoms
(3) Geometrical (4) Tautomerism (4) Length of carbon chain
17. BrCH2–CH2–CH=O and CH3–CH2– C=O are 24. Which of the following compounds will not show
Br cis-trans-isomerism ?
(1) (CH3)2CHCH=CHC2H5
(1) Functional isomers (2) Position isomers
(2) (CH3)2C=CHC2H5
(3) Chain isomers (4) Metamers
(3) CH3CH=CHCH3
18. The two compounds (4) C2H5CH=CHC2H5
21. The total number of aldehydes having the molecular 28. The number of stereo isomers of D–glucose (a six
formula C5H10O is - carbon sugar) is :-
(1) 3 (2) 4 (1) 8 (2) 12
(3) 5 (4) 6 (3) 16 (4) 24
GEOMETRICAL ISOMERISM 29. Optically active isomers but not mirror images are
called -
22. The isomerism shown by Benzaldoxime (1) Enantiomers (2) Mesomers
(3) Tautomers (4) Diastereomers
(1) R (2) S
39. The process of conversion of an optically pure
(3) Both (4) None enantiomer into an optically inactive equimolecular
34. The absolute configuration of the following mixture of (+) and (–) enantiomers is called -
compound is :– (1) tautomerization (2) isomerization
CH3 (3) epimerization (4) racemization
OH OH
(3) CH3 H (4) H CH3
CH2CH3 CH2CH3
O O
(3) Both the above (1) H CH2Cl (2) CH3 C CH
(4) None of the above
7. Which of the following will lead to maximum CH(CH3)2 CH2 OH
enolisation :–
(1) CH3COCH3 CHO COOH
(2) CH3COCH2CHO
(3) H OH (4) H2N H
(3) CH3 C CH C CH3
O Br O CH2 OH CH3
O
(4)
14. Which of the following has E-configuration : 22. The compound which may exhibit tautomerism is-
H3C CH
(1) C C 2 5
H H (1) OH NO (2) HN O
BrCH2 CH3
(2) C C
H3C C2H5 O
Br CH(CH3)2 (3) (4) All the above
(3) C C
HOCH2 CH2 CH3
CHO
Cl H
(4) C C 23. Which of the following compounds can exhibit
Br D
geometrical isomerism ?
15. The priority of groups OH, COOH, CHO, OCH3
attached to chiral carbon is in order - (1) 2–Pentyne (2) 2–Pentene
(3) 2–Methylpropene (4) 2–Methyl–2–butene
(1) OH > COOH > CHO > OCH3
24. The IUPAC name of the compound
(2) OCH3 > OH > CHO > COOH
(3) OCH3 > OH > COOH > CHO Cl CH2CH3
C=C is-
(4) OCH3 > COOH > CHO > OH H3C I
16. (+)-Tartaric acid and meso-tartaric acid are - (1) trans–2–chloro–3–iodo–2–pentene
(1) Enantiomers (2) Diastereomers (2) cis–2–chloro–3–iodo–2–pentene
(3) geometric isomers (4) None of these (3) trans–3–iodo–4–chloro–3–pentene
17. Tautomerism is not exhibited by :- (4) cis–3–iodo–4–chloro–3–pentene
25. The correct structure of trans–2–hexenal is -
(1) (2) (CH3)2CHNO2 CHO
(1)
(2)
CHO
(4) CHO
18. Given compound exhibits x geometrical isomers and 26. How many alcohols (neglecting stereoisomers) are
y optical isomers possible with the molecular formula C5H12O
(1) 5 (2) 6
(3) 7 (4) 8
27. The total number of benzene derivatives having the
molecular formula C7H8O is -
The value of x and y respectively are :- (1) 3 (2) 4
(1) 4 and 4 (2) 2 and 2 (3) 5 (4) 6
(3) 2 and 4 (4) 4 and 2 28. The number of carbon atoms present in the smallest
acyclic hydrocarbon capable of showing cis-trans
19. The total number of cyclic compounds (neglecting isomerism is -
stereoisomers) with the molecular formula C 5H10
is - (1) 3 (2) 4
(3) 5 (4) 6
(1) 4 (2) 5
29. The total number of amines (neglecting
(3) 6 (4) 7 stereoisomers) possible with the molecular formula
20. Which of the following exhibits tautomerism ? C3H9N is-
(1) (CH3)2NH (2) (CH3)3CNO2 (1) 2 (2) 3
(3) 4 (4) 5
(3) R3CNO2 (4) RCH2NO2
21. The two compounds CH 3CH 2CH 2OCH 3 and 30. The total number of benzene derivatives with the
molecular formula C6H3Cl3 is -
CH3CH2OCH2CH3 may be considered as :
(1) metamers (2) tautomers (1) 2 (2) 3
(3) 4 (4) 5
(3) functional isomers (4) position isomers
31. A molecule is said to be chiral, only if 38. Consider the following structures (A), (B), (C)
(1) it is superimposable on its mirror image and (D) -
(2) it is non-superimposable on its mirror image
CH3 C2H5
(3) it possesses stereogenic centres
(4) it can have different configurations Cl Br Cl Br
32. Which of the following compounds is not chiral ? C2H5 CH3
(1) DCH2CH2CH2Cl (A) (B)
(2) CH3CHDCH2Cl
(3) CH3CHClCH2D Cl Cl
(4) CH3CH2CHDCl CH3 Br C2H5 CH3
33. The total number of stereoisomers of 2,3–
C2H5 Br
dibromobutane is -
(C) (D)
(1) 2 (2) 3
(3) 4 (4) 5 Which of the following statements is not correct
34. How many primary amines are possible with the (1) B and C are identical
molecular formula C4H11N (2) A and B are enantiomers
(1) 2 (2) 3 (3) A and C are enantiomers
(3) 4 (4) 5 (4) B and D are enantiomers
35. According to CIP Sequence rule, the correct 39. The interchange of two groups (Br and CH3) at the
arrangement in order of decreasing priority is - chiral centre of the projection formula (A) yields
(1) –OH > CH2OH > –CHO > –COOH the formula (B), while the interchange of another
(2) –OH > COOH > –CHO > –CH2OH set of two groups (C2H5 and Cl) of (A) yields the
(3) –COOH > OH > –CHO > –CH2OH projection formula (C) -
(4) –COOH > CHO > –CH2OH > –OH
CH3 Br CH3
36. In the structure
CH3 Cl Br Cl CH3 C2H5 Br
H OH C2H5 C2H5 Cl
H Br
(A) (B) (C)
CH3
Which of the following statements is not correct
the configurations at the chiral centres are
about the structures (A), (B) and (C) -
(1) 2R, 3R (2) 2S, 3R
(1) B and C are identical
(3) 2R, 3S (4) 2S, 3S
(2) A and C are enantiomers
37. Which of the following compounds contains a
(3) B and C are enantiomers
pseudo-asymmetric carbon atom
(4) A and B are enantiomers
(1) CH3CHCHCH2
Br Br Br 40. Which of the following compounds exists as a
nonresolvable racemic mixture ?
(2) CH3CH–CH–CHCH3 (1) CH3CH2CH(OH)CH2CH3
Br OH Br (2) CH3CHOHCOOH
OHBr Br CH3
+ –
(4) C2H5–N–CH(CH3)2Br
(4) CH3CHCHCHCH3
C2H5
Br OHCl
41. The process of separating a racemic mixture into 43. The correct configuration assigned for compounds
optically pure (+) and (–) enantiomers is known as- (I) and (II) respectively are :-
1. The enolic form of acetone contains [IIT-90] 8. The number of possible enantiomeric pairs that
(1) 9 bonds, 1 bond and 2 lone pairs can be produced during monochlorination of
(2) 8 bonds, 2 bonds and 2 lone pairs 2–methyl butane is – [IIT-97]
(3) 10 bonds, 1 bonds and 1 lone pair (1) 2 (2) 3 (3) 4 (4) 1
(4) 9 bonds, 2 bond and 1 lone pair
9. Tautomerism is not exhibited by– [IIT-98]
Me H Me CH3 O CH3
(I) (II)
H H
Me H + C2H5 CH C2H5
H C
CH3
H
(IV)
(1) optically active compound (III)
CH2CH3 H
(3) CH3 C
in terms of isomerism in-
C2H5
(1) chain isomerism (2) position isomerism
(3) conformers (4) stereo isomerism (4) CH3 CH2 CH2 CH3
24. Which of following compounds is not chiral 30. The number of stereoisomers obtained by
(1) 1–chloropentane [AIEEE-2005] bromination of trans–2–butene is– [IIT-2007]
(2) 2–chloropentane (1) 1 (2) 2
(3) 1–chloro–2–methyl pentane (3) 3 (4) 4
31. Which one of the following conformations of
(4) 3–chloro–2–methyl pentane
cyclohexane is chiral ? [AIEEE - 2007]
(1) Twist boat (2) Rigid
25. Of the five isomeric hexanes, the isomer which can
give two monochlorinated compounds is- (3) Chair (4) Boat
32. Which of the following molecules is expected to
(1) 2-methyl pentane [AIEEE-2005]
rotated the plane of plane-polarised light ?
(2) 2,2–dimethyl butane [AIEEE - 2007]
(4) n-hexane HO H
(1) (2)
SH
CH2OH
CH3
Cl2/hv
27. CH3–CH–CH2–CH3 N (no. of isomers) HOC
2 CO2H
33. The absolute configuration of
HO H H OH
Fractional distillation
(F), (N) and (F) are–
[IIT-2006] is [AIEEE - 2008]
(1) S, S (2) R, R
(1) 6, 4 (2) 4, 4
(3) R, S (4) S, R
(3) 6, 6 (4) 3, 3
34. D glu cos e and D glu cos e
28. Increasing order of stability among the three main
are [AIEEE - 2008]
conformations (i.e. Eclipse, Anti, Gauche) of
2-fluoroethanol is [AIEEE-2006] (1) conformers (2) epimers
(2) Eclipse, Anti, Gauche 35. The alkene that exhibits geometrical isomerism
is :- [AIEEE - 2009]
(3) Anti, Gauche, Eclipse
(1) 2–butene (2) 2–methyl–2–butene
(4) Eclipse, Gauche, Anti (3) Propene (4) 2–methyl propene
29. The number of structural isomers C6H14 is– 36. The number of stereoisomers possible for a
(1) 3 (2) 4 [IIT-2007] compound of the molecular formula
(1) 4 (2) 6
(3) 3 (4) 2
37. The correct statement(s) about the compound given 39. Out of the following, the alkene that exhibits optical
below is (are) :- [IIT-2008] isomerism is :- [AIEEE-2010]
Cl H
(3) 4-methyl-1-pentene (4) 3-methyl-1-pentene
40. Identify the compound that exhibits
(1) The compound is optically active tautomerism :- [AIEEE-2011]
(2) The compound possesses centre of symmetry (1) 2-Pentanone (2) Phenol
(3) 2-Butene (4) Lactic acid
(3) The compound possesses plane of symmetry
41. How many chiral compounds are possible on
(4) The compound possesses axis of symmetry
monochlorination of 2–methyl butane ?[AIEEE-2012]
38. The correct statement(s) concerning the structures (1) 6 (2) 8 (3) 2 (4) 4
E, F and G is (are) [IIT-2008] 42. Which branched chain isomer of the hydrocarbon
with molecular mass 72 u gives only one isomer of
H3C O mono substituted alkyl halide ? [AIEEE-2012]
(1) Neohexane (2) Tertiary butyl chloride
H3C CH3
(3) Neopentane (4) Isohexane
(E)
43. How many cyclic structures are possible for
OH C4H6 :- [AIEEE-2012(Online)]
H3C
(1) 3 (2) 5 (3) 4 (4) 6
H3C CH3
(F) 44. Maleic acid and fumaric acids are :-
(1) Tautomers [AIEEE-2012(Online)]
H3C CH3 (2) Chain isomers
H3C OH (3) Geometrical isomers
(G) (4) Functional isomers
(1) E, F and G are resonance structures
(2) E, F and E, G are tautomers
(3) F and G are geometrical isomers
(4) F and G are diastereomers