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ATP Star 2
ATP Star 2
CHEMISTRY
Target IIT JEE-2021
WARRIOR
SHEET - ISOMERISM
EXERCISE - I
JEE MAIN LEVEL
Single correct questions :
1. Examine the relation between the following pairs of compounds.
Cl OH
Cl Cl OH OH
(I) and (II) and
Cl OH
COOH
COOH
(III)
and
HOOC COOH
(A) All I, II, III are identical (B) All I, II, III are isomers
(C) I, II are identical, III is isomer (D) I is identical and II, III are isomer
OH OH
| |
2. CH3 CH2 CH2 CH2 and CH3 C CH3 are
|
CH3
(A) chain isomers (B) positional isomers (C) both (D) none
4.
How many structural isomers are possible when one of the hydrogen is replaced by chlorine atom
(A) 4 (B) 8 (C) 7 (D) 6
8. In the complete rotation of butane from 0º to 360º the gauche (straggered) conformation appears
(A) once (B) Twice (C) Thrice (D) Four times
O = – CH3
H H
H H
(A) 45° (B) 90° (C) 120° (D) 180°
2
15. The total number of geometrical isomers possible in following compound is :
CH=CH–CH=CH
19. Total number of geometric diastereomers exist for 1, 3-dichloro-2, 4-dimethyl cydobutane?
(A) 3 (B) 4 (C) 5 (D) 6
HO OH HO OH
HO OH HO OH
I II III IV
(A) I & II (B) II & III (C) III & IV (D) II & IV
Cl Cl Cl Cl
3
25. Which of the following structures represents a chiral compound ?
CH3 CH3 CH3 CH3 CH3
CH3
H H CH3 CH3 CH3
H H
(A) CH3 CH3 (B) CH3 CH3 (C) CH3 CH3 (D) CH
3 CH3
H OH H CH3 HO OH
H CH3
26. Examine the compound on the right. How many stereoisomers having this constitution are possible ?
CH3
H3C
O
H3C
CH3
Br
CH3
CH3
(A) 2 (B) 4 (C) 6 (D) 8
27. How many stereoisomers are possible for the following molecule.
Cl
Br CH = CH
CH3
28. Which of the following heptanols are chiral 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol.
(A) All are chiral (B) 2-heptanol and 3-heptanol
(C) 2-heptanol, 3-heptanol & 4-heptanol (D) 3-heptanol and 4-heptanol
29. The necessary and sufficient condition for a molecule to be optically active :
(A) It must contain asymmetric carbon atoms (B) It must be chiral atom
(C) It must be identical with its mirror image (D) It must be non-superimpossable with its mirror image
CH3 CH3
H Cl H Cl is
30. Optical rotation produced by Cl H is 36° then that product by H Cl
CH3 CH3
31. Which of the following sugars has the configuration (2S, 3R, 4R) ?
4
33. Meso tartaric acid and d-tartaric acid are
(A) Position isomers (B) Enantiomers (C) Diastereomers (D) Racemic mixture
37. Sum of stereoisomer in the given compound (a) and (b) are
Cl
Cl Cl = a (stereoisomer) ; = b (stereoisomer)
Cl
a+b=?
(A) 3 (B) 4 (C) 5 (D) 6
5
F Br
I H Cl CH3
41. What is the relationship between (I) & (II) Br CH3 I H
Cl F
(I) (II)
(A) Enantiomer (B) Diastereomers (C) Constitutional isomer (D) Identical molecules
Subjective questions :
42. Among the following How many compounds are chiral ?
H3C H3C
43. Among the following compounds how many has a stereoisomer that is a meso compound ?
(a) (i) 2,3-dimethylbutane (ii) 2-bromo-3-methylpentane (iii) 1-bromo-2-methylcyclohexane
(b) (i) 3,4-dimethylhexane (ii) 3,4-diethylhexane
(c) (i) 1,3-dimethylcyclohexane (ii) 1,4-dimethylcyclohexane (iii) 1,2-dimethylcyclohexane
H Br & Br H
(iii) Cl & H Cl (iv) H
Br H H Br
H Cl Cl H
CH2H CH2CH3
H H
CH3 H CH3 Et
H CH3 Et
(vii) CH3 & (viii) H & Me H
Me
Me H
H Me
CH3 CH3
Et
Et
Br Br
H
H H H H H H H
H Br Br
(ix) & (x) &
H Et H H Et Br OH
H OH H OH
OH
6
EXERCISE - II
PREVIOUS YEAR AIEEE/JEE-MAIN QUESTIONS
Single Choice Questions :
1. A similarity between optical and geometrical isomerism is that [AIEEE-2002]
(A) each forms equal number of isomers for a given compound
(B) If in a compound one is present then so is the other
(C) both are included in stereoisomerism
(D) they have no similarity
CH2–CH3
OH CH3
O
7
8. Among the following four structures I to IV [AIEEE-2003]
10. Amongst the following compound, the optically active alkane having lowest molecular mass is
[AIEEE-2004]
13. Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche) of 2-fluoroethanol
is [AIEEE-2006]
(A) Eclipse, Gauche, Anti (B) Gauche, Eclipse, Anti
(C) Eclipse, Anti, Gauche (D) Anti, Gauche, Eclipse
14. Which of the following molecules is expected to rotate the plane of plane polarized light ? [AIEEE-2007]
CHO COOH
H2N NH2
HO H H2N H
(A) (B) (C) H H (D)
SH Ph Ph
CH2OH H
HO2C CO2H
16. The absolute configuration of is [AIEEE-2008]
HO H OH
H
(A) S, S (B) R, R (C) R, S (D) S, R
8
17. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]
(A) 2-butene (B) 2-methyl-2-butene (C) propene (D) 2-methyl propene
18. The number of stereoisomers possible for a compound of the molecular formula [AIEEE-2009]
CH3 – CH = CH – CH(OH) – Me is :
(A) 4 (B) 6 (C) 3 (D) 2
20. Out of the following, the alkene that exhibits optical isomerism is [AIEEE-2010]
(A) 3-methyl-1-pentene (B) 2-methyl-2-pentene
(C) 3-methyl-2-pentene (D) 4-methyl-1-pentene
9
EXERCISE - III
JEE ADVANCED LEVEL
Single Choice Questions :
1. Which of the following is correct set of physical properties of the geometrical isomers
CH3 H CH3 Cl
C=C & C=C
H Cl H H
(I) (II)
CH3
CH2–CH=CH–CH=N–OH
O OH O
|| | ||
3. S – CH = CH – CH – C – CH3
..
Number of chiral centers are.
(A) 1 (B) 2 (C) 3 (D) 4
C2H5 C2H5
CH3 H CH3
H OH H OH
OH HO H H
OH H
(A) HO H (B) (C) H OH (D) H OH
CH3 H CH3 C2H5 CH3
5. Which of the following compounds has two stereogenic centers (asymmetric carbons) ?
Cl
Cl Cl O
|| O H
||
10
6. How many stereoisomers are possible for the following compound?
NO2 CHBrMe
CH=CHMe I
(A) 2 (B) 4 (C) 6 (D) 8
7. Which of the following statements must be true for two pure chiral isomers ?
(A) they must be enantiomers (B) they must be diastereomers
(C) they must be stereoisomers (D) they must be optically active
HO CH=CH–CH=CH–CH2–CH2–CH3
(A) 8 (B) 16 (C) 64 (D) 128
11. Match List I with List II and select the correct answer from the codes given below the lists:
List I
O O
|| ||
(A) CH 3 C O CH 2 CH 2 CH 3 and CH 3 CH 2 C O CH 2 CH 3
(B) and
(C) and
11
(D) and
List II
(1) Enantiomer (2) Position isomers (3) Metamers (4) Tautomers
Codes :
(A) (B) (C) (D) (A) (B) (C) (D)
(A) 3 2 4 1 (B) 3 2 1 4
(C) 1 2 3 4 (D) 2 3 4 1
(C) (D)
Me Cl
Me
13. Which of following pair is Diastereomers:
CO2H
H OH CO2H CH3 H CH3
H OH
H
CH3 C C H
(A) H OH (B) C=C Br Br
HO H
C=C
CO2H CO2H H H H CH3
CH3 Et Cl Cl
H OH HO H Cl Cl
(C) H SH HS H (D)
Et CH3 Cl Cl
Me
Me
14. H
H
Incorrect statement about this compound is:
(A) It shows geometrical isomerism (B) It posses centre of symmetry
(C) It posses plane of symmetry (D) It shows optical isomerism
15. Total number of optically active alkyne possible from molecular formula C3FCl BrI
(A) 2 (B) 4 (C) 6 (D) 8
16. Which Fischer projection represents the given wedge dash structure :
Br
H5C2 CH3
H
Br CH3 CH3 Br
Br Br H
(A) H5C2 CH3 (B) H5C2 (C) (D) H3C C2H5
H H C2H5 H
12
17. Which of the following compound posses centre of symmetry ?
Br H O CH3
H N–C CH3 H OH H Cl
H
(A) Cl (B) H C (C) OH H (D)
3 C–N H
H Cl H
Br O CH3
18. Compound that has both center of symmetry and plane of symmetry is/are :
Cl Cl Cl CH3 Cl CH3
20. Which of the following compound has centre of symmetry but not plane of symmetry.
Br Cl Br Cl Br Cl Br Cl
Cl Br Cl Br Cl Br Cl Br
COOH Cl
H OH
(A) (B) (C) Me–CH=C=CH–Me (D)
H OH
Cl
COOH
Me Me
O OH Cl Cl OH OH OH OH Cl Cl OH O
(A) (B)
Me Me Me Me
O OH Cl Cl OH OH OH Cl Cl OH
(C) (D) HO
Me Me Me Me
13
23. Statement-1 : This compound will show geometrical isomerism
27. 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)
28. Which of the following will show optical isomerism as well as geometrical isomerism.
29. Which of the following compounds can show Optical isomerism as well as geometrical isomerism ?
14
30. Which of the following are D sugars:
CHO
H OH
HO H
(A) (B) (C) (D)
H OH
HO–CH2 H
OH
31. The Fischer projection of the molecule as represented in the wedge dash.
and
CO 2H CH2–Br
H H Cl H
H OH
(A) (B) H (C) C=C (D)
OH H
HO OH Cl
CO2H
34. The number of stereoisomers possible for the below compound (do not change cis/trans configurations of the
olefins) are
O CO2H
OH
OH
(A) 8 (B) 16 (C) 32 (D) 12
CHO OH CHO
CH2OH
H OH HO H
(A) (B) H OH (C) H CHO (D)
HO H HO H H OH
CH2OH CH2OH CH2OH
CHO
15
EXERCISE - IV
JEE ADVANCED LEVEL
1. Determine if the following pairs are identical, isomers, enanatiomers, or diastereomers.
OH OH HO OH
(i) _________________
OH
OH
(ii) _________________
CHO CH2OH
H OH HO H
(iii) H OH HO H _________________
CH2OH CHO
HO
H NH2 OH
H2N H
(i) HO COOH _________________
HOOC OH
L-DOPA
CH2OH CH2OH
H OH H OH
H CH3 H3C H
(ii) _________________
(iii) _________________
CH = O CH = O
CH = O CH = O
H OH HO H
(a) H OH & HO H (b) &
H OH H OH
CH3 CH3
CH3 CH3
Br Br
Br Br Br Br
(c) Br & Br
16
4. Classify each of the following pairs of structures (a)–(e) as
I. Identical E. Enantiomers D. Diastereomers
Br Br
Br Br
(e) &
Br Br
5. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, different compounds that are not isomeric).
OH OH
H H
CH3 CH3
(a) _________________
OH OH CH3
H H
CH3
(b) _________________
OH OH
H H
CH3 CH3
(c) _________________
OH OH
H H
CH3 CH3
(d) _________________
OH OH
H H
CH3 CH3
(e) _________________
17
6. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, conformational isomers, different compounds that are not isomeric).
O O
CH3 CH3
(a) _________________
H3C H3C
O O
CH3 CH3
(b) _________________
H3C H3C
O O
CH3 CH3
(c) _________________
H3C H3C
O O
CH3 CH3
H3C
(d) _________________
H3C
O O
CH3 H3C
(e) _________________
H3C CH3
7. Discuss the optical activity of the following two compounds and also label them as polar and non polar.
(I) (II)
9. A compound with molecular formula C4H10O, can show metamerism, functional isomerism and positional
isomerism. Justify the statement.
10. With reasons, state whether each of the following compounds I to VII is chiral.
18
11. Considering rotation about the C-3 – C-4 bond of 2-methylhexane:
(a) Draw the Newman projection of the most stable conformer.
(b) Draw the Newman projection of the least stable conformer.
Cl Cl
15.
Cl Cl Cl Cl
(a) (b)
Relation between (a) & (b) is
(A) Enantiomer (B) Diastereomer (C) Identical (D) Structural isomer
16. Compound has both center of symmetry and P.O.S
Cl Cl
Cl
Cl
(A) (B) (C) (D)
Cl Cl
19
Paragraph for Question Nos. 17 to 18
If plane-polarized light is passed through one enantiomer of a chiral substance (either the pure enantiomer
or a solution of it), the plane of polarization of the emergent light is rotated. A substance that rotates the
plane of polarized light is said to be optically active. Individual enantiomers of chiral substances are
optically active.
17. HO
18. Which of the following compound show optical isomerism (Assuming cyclobutane ring is planar)
F F
F
(A) F (B) (C) (D)
F F
21. How many total isomers are possible by replacing one hydrogens atoms of propane with chlorine
(A) 2 (B) 3 (C) 4 (D) 5
Matrix Match
22. Column-I Column-II
COOH COOH
(A) A pair of metamer (P) H OH H OH
;
HO H H OH
COOH COOH
CH3 CH3
COOH COOH
O
||
(E) A pair of optical isomer (T) CH3CH2CH2CH ; CH3CH2CH=CH—OH
20
23. Match the column :
Column I Column II
Cl Cl
Cl Cl
Cl Cl
Cl
Cl
Cl
Cl Cl Cl
Cl Cl
Cl Cl Cl Cl
Cl Cl
Cl
(D) (S) Identical
Cl
Cl Cl
21
25. Column I Column II
CH3 H
H H3C
CH2OH CH2NH2
(A) and (P) Structural isomer
NH2 OH
CH3 Cl
H H
Cl CH3
(B) and (Q) Identical
Et Et
CH3 H
H H3C
OH Et
(C) and (R) Enantiomers
Et OH
H5C2 H5C2
(D) and (S) Diastereomers
OH H H OH
Subjective questions :
26. Mark each chiral center in the following molecules with an asterisk. How many stereoisomers are possible
for each molecule ?
OH
CH2 – COOH
(a) CH 3CHCHCOOH (b) CH – COOH (c) (d)
HO OH HO–CH–COOH
O OH
(e) O COOH (f) (g)
OH O
27. Following are four Newman projection formulas for tartaric acid.
H OH H OH HO H HO H
COOH COOH H OH
(1) (2) (3) (4)
(a) Which represent the same compound? (b) Which represent enantiomers?
(c) Which represent a meso compound? (d) Which are diastereomers?
22
28. Total number of stereo isomer in 2, 5-dimethyl piperidine
H
|
N
HO
(iii) Number of geometrical isomer of given compound. (z)
N – NH2
H—C—C—C—H
N N
NH2 NH2
23
EXERCISE - V
PREVIOUS YEAR'S JEE QUESTIONS
1. Write structural formulae for all the isomeric alcohols having the molecular formula C4H10O. [JEE 1984]
2. Isomers which can be interconverted through rotation around a single bond are [JEE 1992]
(A) Conformers (B) Diastereomers (C) Enantiomers (D) Positional isomers
6. Which of the following compounds will show geometrical isomerism? [JEE 1998]
(A) 2-butene (B) propene (C) 1-phenylpropene (D) 2-methyl-2-butene
7. Which of the following compounds will exhibit geometrical isomerism? [JEE 2000 (Scr.)]
(A) 1-Phenyl-2-butene (B) 3-Phenyl-1-butene
(C) 2-Phenyl-1-butene (D) 1,1-Diphenyl-1-propene
8. Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III. [JEE 2000]
9. The number of isomers for the compound with molecular formula C2BrClFI is
(A) 3 (B) 4 (C) 5 (D) 6 [JEE 2001 (Scr.)]
10. Which of the following compounds exhibits stereoisomerism? [JEE 2002 (Scr.)]
(A) 2-methylbutene-1 (B) 3-methylbutyne-1
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid
24
11. In the given conformation, if C2 is rotated about C2–C3 bond anticlockwise by an angle of 120° then the
conformation obtained is [JEE 2004 (Scr.)]
4
CH3
H H
3
2
H H
1CH3
(A) fully eclisped conformation (B) partially eclipsed conformation
(C) gauche conformation (D) staggered conformation
15. The correct statement(s) about the compound given below is (are) [JEE 2008]
Cl H
CH3
H3C
Cl H
(A) The compound is optically active
(B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry
16. The correct statement(s) concerning the structures E, F and G is (are) [JEE 2008]
25
17. The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3(X) is (are)
(A) The total number of stereoisomers possible for X is 6 [JEE 2009]
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2
18. The total number of cyclic structural as well as stereo isomers possible for compound with the molecular
formula C5H10 is [JEE 2009]
20. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is
[JEE 2010]
21. Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is (are) [JEE 2011]
H H H
C—C
(A) (B) H — C C—C
H2C CH2 CH2
(C) H2C = C = O (D) H2C = C = CH2
22. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [JEE 2012]
(A) sp and sp 3 (B) sp and sp 2 (C) only sp2 2
(D) sp and sp3
23. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ? [JEE 2012]
HO HO Cl
H H CH3 CH3
H OH H OH HO H
Cl CH3
HO H H OH HO H
HO H HO H
CH3 Cl CH3 Cl Cl
M N O P Q
(A) M and N are non-mirror image stereoisomers (B) M and O are identical
(C) M and P are enantiomers (D) M and Q are identical
24. The total number of stereoisomers that can exist for M is [JEE Advance 2015]
H3C CH3
H3C
M
O
26
ANSWER KEY
EXERCISE-I
1. C 2. A 3. C 4. C 5. C 6. A 7. C
8. B 9. C 10. A 11. B 12. C 13. A 14. D
15. C 16. D 17. C 18. D 19. C 20. B 21. C
22. A 23. C 24. C 25. D 26. D 27. C 28. B
29. D 30. B 31. C 32. D 33. C 34. B 35. C
36. A 37. C 38. D 39. A 40. B 41. B
42. 2 (c, e) 43. (a) 0, (b) 1, (c) 2 44. 4 (i, iii, iv, viii)
EXERCISE-II
1. C 2. C 3. D 4. B 5. D 6. D 7. B
8. B 9. D 10. D 11. A 12. B 13. C 14. A
15. A 16. B 17. A 18. A 19. D 20. A 21. C
22. B
EXERCISE - III
1. C 2. B 3. B 4. A 5. D 6. D 7. D
8. C 9. A 10. D 11. A 12. A 13. B 14. B
EXERCISE - IV
1. (i) Diastereomers (ii) Enantiomers (iii) Identical
2. (i) Identical (ii) Diastereomers (iii) Diastereomers
3. (a) E (b) D (c) I
4. (a) E (b) I (c) D (d) I (e) E
5. (a) Diastereomer (b) Diastereomer (c) Not isomer (d) Structural (e) Enantiomer
6. (a) Diastereomer (b) Not isomer (c) Enantiomers (d) Structural isomers (e) Identical
7. Compound I is optically inactive since it contain a plane of symmetry. Compound II is enantiomeric since it
does not contain plane of symmetry, hence chiral. Also compound I is polar while II is non polar ]
8. 3
9. (i) Et – O – Et, (ii) CH3 – O – CH2 – CH2 – CH3, (iii) CH3 – CH2 – CH2 – CH2 – OH, (iv) CH3 – CH2 – CH – CH3
|
I & II metamers, I & III functional isomers, III & IV position isomers OH
10. achiral : I, III ; chiral : II, IV, V, VI
Et
Et
H H
11. (a) (b)
H H
H
H H
H
27
12. D 13. C 14. B 15. B 16. D 17. B 18. B
19. A 20. C 21. A
22. (A) Q; (B) T; (C) S; (D) P, S; (E) P, R 23. (A) Q, S ; (B) Q, S ; (C) P, S ; (D) Q, R
24. (A) R, (B) P, (C) S, (D) S 25. (A) P ; (B) R ; (C) Q ; (D) R
26. (a) 4 (b) 4 (c) 2 (d) 8 (e) 4 (f) 4 (g) 4
27. (a) 3 & 4 (b) 1 & 3, 1 & 4 (c) 2 (d) 1 & 2, 2 & 3, 2 & 4
28. 4 (ae, aa, ee, ea) 29. 12 + 11 + 4 = 27
EXERCISE - V
1. 4 2. A 3. B 4. B 5. D 6. A 7. A
8. enantiomers–I & III; diastereomers – I & II and II & III 9. D 10. D 11. C
1
12. (i) D (ii) Anti form when Y = CH3 & Gauche when Y = – OH
0.18
13. C 14. C 15. A, D 16. B,C,D 17. A, D 18. 7 19. B, D
20. 5 21. B, C 22. B 23. A,B,C 24. 2
28