Stereochemistry (Csir-Net/Gate)

Stereo Chemistry Assignment ( NET/GATE) 1
STEREOCHEMISTRY (CSIR-NET/GATE)
(Question with 2 Marks)
1. The configuration at the two stereocentres in the compound given below are:
Me O
1
4
H
(a) 1R, 4R (b) 1R, 4S (c) 1S, 4R (d) 1S, 4S
2. The two compounds given below are:
O O
Me Me
and
H H
(a) Enantiomers. (b) Identical. (c) Diastereomers. (d) Regioisomers.
3. In the compound given below, the hydrogens marked A and B are:
O
Ph N Ph
HB HA
COOH
(a) Homotopic. (b) Isotopic. (c) Enantiotopic. (d) Diastereotopic.
4. The absolute configuration at the two chiral centers of (–)–camphor is:
O
1
4
(a) 1R, 4R (b) 1R, 4S (c) 1S, 4R (d) 1S, 4S
5. In the following Markonikov addition reaction, the products A and B are:
HBr
A+B
Br
(a) Homomers. (b) Enantiomers. (c) Diastereomers. (d) Regioisomers.
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6. Among A-C, the compounds which can exhibit optical activity are:
(I) (II) (III)
(a) I, II and III (b) I and II only (c) I and III only (d) II and III only
7. Epoxidation of (R)-cyclohexene-2-ol with peracetic acid yields a 95:5 mixture of compounds A and
B compounds A and B are:
(a) Enantiomers. (b) Diastereomers.
(c) Constitutional isomers. (d) Homomers.
8. Among the following the most stable isomer for 3-methoxycyclohexanol is:
(a) (b) (c) (d)
9. What is the relation between shown compounds:
(a) Enantiomers. (b) Diastereomers. (c) Same. (d) None of these.

10. Which species exhibits a plane of symmetry
OH
H COOH
(a) (b) (c) (d)
HOOC
OH
11. Which of the following term best describes the pair of compound shown:
(a) Enantiomers. (b) Diastereomers. (c) Same. (d) Meso.
12. The most stable conformation for the following compound is:
(a) (b)
(c) (d)
13. Among the following dibromocyclohexanes, the one that reacts fastest with sodium iodide to give
cyclohexene is:
(a) (b) (c) (d)
14. An aqueous solution of an optically pure compound of concentration 100 mg in 1 ml of water and
measured in a quartz tube of 5 cm length was found to be –3°. The specific rotation is:
(a) –30° (b) –60° (c) –6° (d) +6°
15. The absolute configuration of the chiral centers of starting ketone in the following reaction is:
(a) 3R, 6S (b) 3S, 6S (c) 3R, 6R (d) 3S, 6R

16. Which of the following term best describes the pair of compound shown:
(a) Diastereomers. (b) Enantiomers. (c) Meso. (d) None of these.
17. The most stable conformation of the following compound is:
(a) (b) (c) (d)
18. The correct order of stability for the following conformations of cyclohexane is:
(I) (II) (III)
(a) I > II > III (b) I > III > II (c) II > I > III (d) III > I > II
19. Ring flipping of the compound in the following conformation leads to:
(a) (b) (c) (d)
20. The compound in ‘R’ configuration is:
(a) (b)
(c) (d)
21. Draw the structure of (2R, 3S) – 2, 3 – dichloropentane

Cl Cl
(a) H3C C C CH2 CH3 (b)
H H
(c) Both. (d) None of these.
22. The most stable confirmation of following compound is:
(a) (b) (c) (d)
23. Structure of 1, 2-dimethylcyclohexane is show below. Which of the following is an enantiomer to

the given conformer:
(a) (b) (c) (d)
24. Which is the most stable conformation of 1-chloro-4-methylcyclohexane?

Cl
H H
H
(a) (b) (c) H3C Cl (d) H
CH3
25. Which of the following structure representation is R-Lactic acid?
COOH
(I) (II) (III) H CH3
OH
(a) I only (b) II only (c) III only (d) None of these
26. The favored conformation (gauche, anti) for the molecule 1, 2-dichloro ethane; and 1,2-ethanediol
will be respectively.
(a) Gauche, anti (b) Eclipsed, gauche (c) Anti, gauche (d) Anti, eclipsed
27. Which of the following term best describes the pair of compound shown below:
(I) (II)
(a) Diastereomers (b) Enantiomers (c) Both (d) None of these
28. The major product is formed in the following reaction is:
CH3
Br H
(a) (b) (c) (d)
H Br
CH3
29. How many asymmetric carbons are present in the compound:
(a) 2 (b) 3 (c) 5 (d) 4

30. How many asymmetric carbons are present in the following compound:
CO2H
H OH
H OH
CO2H
(a) 5 (b) 1 (c) 4 (d) 2
31. The configurations at the three chiral centres in the bicyclodecanol given below, are:
(a) 1S, 2S, 6R (b) 1S, 2S, 6S (c) 1R, 2S, 6R (d) 1R, 2S, 6R
32. The S enantiomer of ibuprofen is responsible for its pain – relieving properties. Which one of the
following structures shown in (S) – ibuprofen?
(a) (b)
(c) (d)
33. Consider the following statements:

(I) Enantiomers in which there is restricted rotation about (C–C) single bond are called
astropisomers.
(II) 2, 3-pentadiene is chiral and can exist as pair of enantiomers.
(III) 2, 3-pentadiene can exist as cis and trans-isomers.

(IV) 2, 3-pentadiene is achiral and meso compound.
Select the correct statements.
(a) I, II, IV (b) II, III (c) I, IV (d) I, II
34. The major product formed in the following reaction is:
(a) (b) (c) (d)
35. Draw the structure of (1 R, 2 S, 3 S)-1, 2-dibromo-3-ethyl cyclohexane:
(a) (b) (c) (d)
36. The molecule(s) that exist as meso structure(s) is/are:
(I) (II) (III)
(a) III only (b) Both I and II (c) II only (d) I only
37. The absolute configurations of the chiral centers in X and Y are:
CHO
HCN
H OH X+Y
CH2OH
(a) 2S, 3R and 2R, 3R (b) 2R, 3R and 2R, 3S (c) 2S, 3S and 2R, 3R (d) 2S, 3R and 2S, 3R
38. Stereoisomers which are not mirror image isomers are:
(a) Enantiomers (b) Diastereomers (c) Meso compounds (d) None of these
39. Racemisation process is:
(a) Conversion of an optically active compound into the racemic modification
(b) Conversion of an optically inactive compound into the racemic modification
(c) Both
(d) None of the above
40. The configuration of the following position of (I) and (II) is:
HO
HO2C (I)
(II) CO2H
OH
(a) 1 → S, 2 → R (b) 1 → R, 2 → S (c) 1 → R, 2 → R (a) 1 → S, 2 → S
41. Resolution is called as:
(a) A separation of two enantiomers (b) A separation of two Diastereomers
(c) Both (d) None of the above
42. Which is the correct structure of D-Glyceraldehyde:
(a) (b) (c) (d) All of these.
43. Which of the following structure represents meso compounds:
(a) (b) (c) (d) All of these.
44. The two compounds shown below are:
(a) Diastereomers (b) Epimers (c) Enantiomers (d) Regiomers

45. Which of the following statements is true for the compound (R)-2-butanol?
(a) This compound is chiral (b) This compound is optically active
(c) This compound has an enantiomer (d) All of the above
46. Methyl groups in the following compound are:
(a) Homotopic (b) Diasterotopic

(c) Enantiotopic (d) Constitutionally heterotopic
47. What kind of isomers are the two compound below:
(a) Configuration diastereomers (b) Enantiomers

(c) Constitutional isomers (d) They are exactly the same compounds.
48. Among the structures given below, the most stable conformation for the following compound is:
(a) (b) (c) (d)
49. The correct statement about the following compound is:
(a) Compound is chiral and has P configuration.

(b) Compound is chiral and has M configuration.
(c) Compound is achiral as it possesses C2-axis of symmetry.
(d) Compound is chiral as it possesses plane of symmetry.
50. Which of the following term correctly describes the structural relationship between cis-1,3-dimethyl
cyclopentane and trans-1,3-dimethyl cyclopentane:
(a) Enantiomer (b) Diastereomer (c) Geometric Isomer (d) Regioisomer
(Question with 4 Marks)
51. The gauche conformation (   60 ) of n-butane possess:
(a) Plane of symmetry; and is achiral (b) C2-axis of symmetry; and is chiral
(c) Centre of symmetry; and is achiral (d) Plane of symmetry; and chiral
52. The constituent amino acids present in following dipeptide, respectively, are:
(a) (R)-aspartic acid and (S)-lysine (b) (S)-aspartic acid and (R)-lysine
(c) (R)-glutamic acid and (S)-arginine (d) (S)-glutamic acid and (S)-arginine
53. The absolute configuration of the two stereogenic (Chiral) centers in the following molecule is:
(a) 5R,6R (b) 5R,6S (c) 5S,6R (d) 5S,6S

54. The correct statement about the following molecule is:
Br
Br
(a) Molecule is chiral and possesses a chiral plane
(b) Molecule is chiral and possesses a chiral axis
(c) Molecule is achiral and possesses a plane of symmetry
(d) Molecule is achiral and possesses a centre of symmetry
55. Consider following the statement about cis- and trans-decalin:
(A) cis-isomer is more stable than trans-isomers. (B) trans-isomer is more stable than cis-isomers.
(C) trans-isomer undergoes ring-flip. (D) cis-isomer undergoes ring-flip.
The correct statement among the above are
(a) B and D (b) A and C (c) A and D (d) B and C
56. In the most stable conformation of neomenthol, stereochemical orientation of the three substituents
on the cyclohexane ring are:
(a) OH: equatorial; i-Pr: equatorial and Me: equatorial.
(b) OH: axial; i-Pr: equatorial and Me: equatorial.
(c) OH: equatorial; i-Pr: equatorial and Me: axial.
(d) OH: equatorial; i-Pr: axial and Me: equatorial.
57. The gauche interaction values for Me/Me, Me/Br and Br/Br are 3.3, 0.8 and 3.0 kJ/mol, respectively.
Among the following, the most stable conformation of 2,3-dibromobutane is:
Br
H Me
(a) (b) (c) (d)
Me H
Br
58. The most stable conformations of 1,2-difluoroethane and dl-2, 3-butanediol are:
(a) (b)
(c) (d)
59. Among the following, the optically inactive compound is:
(a) (b)
(c) (d)
60. Bridge-head hydrogen of the conformer of cis-decalin is positioned as:

(a) a,a (b) e,e (c) a,e (d) pseudo-a,pseudo-e
61. The binaphthol (Bnp) is:
(a) An optically active compound with (R)-configuration

(b) An optically inactive compound
(c) A meso compound
(d) An optically active compound with (S)-configuration
62. Cis and trans-2-methyl-5-t-butyl-1,3-dioxane each can exist as two conformers as shown below:
The preferred conformations for the cis-and trans-compounds will be

(a) P,R (b) Q,S (c) P,S (d) Q,R
63. Identify the correct stereochemical relationship among the hydrogen atoms Ha, Hb and Hc in the
following compound:
(a) Ha, and Hb: enantiotopic (b) Ha, and Hb : diastereotopic

(c) Ha, and Hc: enantiotopic (d) Hb, and Hc : diastereotopic
64. Identify the CORRECT set of stereochemical relationships amongst the following monosaccharides
I-IV:
(I) (II) (III) (IV)
(a) I and II are anomers: III and IV are epimers (b) I and III are epimers: II and IV are anomers
(c) I and II are epimers: III and IV are anomers (d) I and III are anomers: I and II are epimers
65. The stereochemical descriptors for the atoms labeled Ha and Hb in the structures respectively are:
(X) (Y) (Z)
(a) X-homotopic, Y-enatiotopic and Z-diastereotopic

(b) X- enatiotopic Y- homotopic and Z- diastereotopic
(c) X- diastereotopic Y- homotopic and Z- enantiotopic
(d) X- homotopic Y- diastereotopic and Z- enatiotopic
66. For the compound the stereochemical notations are:
(a) 2Z, 4R (b) 2Z, 4S (c) 2E, 4R (d) 2E,4S

67. The absolute configurations for compounds, X and Y respectively are:
(X) (Y)
(a) R, S (b) S, R (c) R,R (d) S,S

68. Among the following, a pair of resolvable Configurational enantiomers is given by:
(a) cis-1, 2 dimethylcyclohexane (b) cis-1, 3 dimethylcyclohexane
(c) cis-1, 4 dimethylcyclohexane (d) trans-1, 3 dimethylcyclohexane
69. In the reaction the major product [X] is:
HOAc, KOAc
Optically pure(  )  trans  acetoxycyclohexyl tosylate 
[X]

(a) Racemic trans-1, 2-cyclohexanediol diacetate
(b) Optically active trans-1, 2- cyclohexanediol diacetate
(c) Racemic cis-1, 2-cyclohexanediol diacetate
(d) Optically active cis-1, 2-cyclohexanediol diacetate
70. The maximum number of stereoisomers possible for the compound given below is:
(a) Two (b) Four (c) Six (d) Eight

71. The major product formed in the following reaction is:
SPh SPh OH
(a) (b) (c) (d)
OH OH SPh
H H H
72. Consider the following reaction, among a–c, the correct statements are:
(I) The carbonyl group has enantiontopic faces; (II) The hydride attack is re-facial;
(III) It is a diastereoselective reduction.
(a) I and II only (b) I and III only (c) II and III only. (d) I, II and III
73. Among the choices, the correct statements for A formed in the following reaction:
(a) A is a single enantiomer. (b) A is a racemic mixture.

(c) A is a mixture of two Diastereomers. (d) A is a mixture of two epimers.
74. Given the energy of each gauche butane interaction is 0.9 kcal/mol, ∆G value of the following
reaction is:
(a) 0.9 kcal/mol. (b) 1.8 kcal/mol. (c) 2.7 kcal/mol. (d) 3.6 kcal/mol.
75. The result of the reduction of either (R) or (S) 2-methylcyclohexanone, in separate reactions, using
LiAIH4. Is that the reduction of:
(a) The R enantiomer is stereoselective. (b) The R enantiomer is stereospecific.
(c) The S enantiomer is stereospecific. (d) Both the R and S enantiomers is stereoselective.
76. The most stable conformation of 2-fluoroethanol is:
H OH
(a) F (b) (c) (d)
H H
H
77. In the most stable conformation of trans-1-t-butyl-3-methylcyclohexane, the substituents at C–1 and
C–3, respectively, are:
(a) Axial and equatorial (b) Equatorial equatorial
(c) Equatorial and axial (d) Axial and axial
78. Match the following:
Column I Column II
(A) (i) Chiral centre
(B) (ii) Chiral axis
(C) (iii) Chiral plane
(a) (A)-iii, (B)-ii, (C)-iv (b) (A)-iv, (B)-iii, (C)-ii

(c) (A)-ii, (B)-iv, (C)-iii (d) (A)-ii, (B)-iii, (C)-iv
79. The IUPAC name of the following compound is:
(a) (R)-3-(prop-2-enyl) hex-5-ynoic acid (b) (S)-3-(prop-2-enyl) hex-5-ynoic acid

(c) (R)-3-(prop-2-enyl) hex-5-enoic acid (d) (S)-3-(prop-2-enyl) hex-5-enoic acid
80. An optically active compound enriched with R-enantiomer (60% ee) exhibited []D + 90°. If the
[]D value of the sample is –135°, the ratio of R and S enantiomers would be:
(a) R:S = 1:19 (b) R:S = 19:1 (c) R:S = 1:9 (d) R:S = 9:1
81. The structure of meso-tricarboxylic acid that is formed on potassium per magnate oxidation of
abietic acid is:
(a) (b) (c) (d)
82. In the compound give below, the relation between HA, HB; and between Br1, Br2 is:
(a) HA, HB are enantiotropic; and Br1 Br2 are diastereotopic

(b) HA, HB are diastereotpic; and Br1 Br2 are diastereotopic
(c) HA, HB are diastereotpic; and Br1 Br2 are homotopic
(d) HA, HB are enantiotropic; and Br1 Br2 are homotopic
83. The []D of a 90% optically pure 2-arylpropanoic acid solution is +135°. On treatment with a base a
RT for one hour, []D changed to +120°. The optical purity is reduced to 40% after 3 hours. If so,
the optical purity of the solution after 1 hour, and its []D after 3 hours, respectively, would be:
(a) 80% and 60° (b) 70% and 40° (c) 80% and 90° (d) 70% and 60°
84. Identify the chiral complexes from the following:
(X) [Cr(EDTA)]– (Y) [Ru(bipy)3]3+ (Z) [PtCl(diene)]+
(a) X only (b) X and Y only (c) X and Z only (d) Y and Z only
85. Which one of the following statements is true for the following transformation:
(a) X is the major product and it is a Cram product

(b) X is the major product and it is a anti-Cram product
(c) Y is the major product and it is a Cram product
(d) Y is the major product and it is a anti-Cram product
86. The two benzylic hydrogens HA and HB in the compounds I and II, are
(a) Diastereotopic in I and enantiotopic in II (b) Diastereotopic in II and enantiotopic in I

(c) Diastereotopic in both I and II (d) Enantiotopic in both I and II
87. Consider the following statements about cis- and trans-decalins:
(a) Cis-isomer is more stable than trans-isomer
(b) Trans-isomer is more stable than cis-isomer
(c) Trans-isomer undergoes ring-flip (d) Cis-isomer undergoes ring-flip
88. The most stable conformation for the following compound is:
(a) (b) (c) (d)
89. The hydrocarbon among the following having conformationally locked chair-boat-chair form is:
H H
(a) (b)
H H
H H
(c) (d)
H H
90. Optically pure isomers I and II were heated with NaN3 in DMF. The correct statement from the
following is:
(I) (II) (III) (IV)
(a) I given optically pure IV and II gives optically pure III

(b) I gives racemic mixture of III and II gives optically pure III
(c) I gives optically pure III and II gives racemic III
(d) I gives optically pure IV and II gives racemic IV
91. Identify two enantiomers among the following compounds:
Br CH3 Br H
HC HC
(I) (II) 3 (III) 3 CH3 (IV)
H
Br H Br H
(a) I and II (b) I and III (c) II and IV (d) III and IV
92. Among the following complexes:
(X) [Co(ox)3]3– (Y) Trans-[CoCl2(en)2]+ (Z) [Cr(EDTA)]– the chiral one(s) is/are
(a) X and Y (b) Z and Y (c) Z only (d) X and Z
93. In the following compound, the stereochemical descriptor for Ha and Hb is:
(a) Enantiotopic (b) Diastereotopic

(c) Homotopic (d) Constitutionally heteretopic
94. The correct statements about conformations X and Y of 2-butanone are:
(I) X is more stable than Y (II) Y is more stable than X

(III) Methyl groups in X are anti (IV) Methyl groups in Y are gauche
(a) I and IV (b) I and III (c) II and III (d) I, III and IV
95. The correct order of magnitude of ‘A values’ for the given substituents in cyclohexane derivatives is:
(a) Ph > CN > Me (b) Me > Ph > CN (c) CN > Me > Ph (d) Ph > Me > CN
96. For the reactions shown below, identify the correct statement with regard to the products formed:
(a) P and Q are identical, both are optically active

(b) P and Q are positional isomers, P is racemic and Q is optically active.
(c) P and Q are positional isomers, P is optically active and Q is racemic
(d) P and Q are positional isomers, both are optically active.
97. The major stereoisomer obtained in the reaction of (S)-2-phenylpropanal with MeMgBr is:
CH3
HO H
(a) (b) (c) (d)
H Ph
CH3
98. Ring flipping of the compound in the following conformation leads to:
(a) (b) (c) (d)
99. The compound in ‘R’ configurations is:
(a) (b)
(c) (d)
100. What are the configurations (R or S) of the chiral centers in the following molecules:
(a) Compound 1 = R; Compound 2 = R; Compound 3 = 1S, 2S

(b) Compound 1 = R; Compound 2 = S; Compound 3 = 1R, 2S
(c) Compound 1 = S; Compound 2 = S; Compound 3 = 1S, 2R
(d) Compound 1 = R; Compound 2 = S; Compound 3 = 1S, 2R
ANSWER KEY
1. a 2. b 3. c 4. d 5. c 6. c 7. b 8. a 9. c 10. d
11. a 12. c 13. c 14. b 15. a 16. b 17. c 18. b 19. b 20. a
21. a 22. b 23. b 24. a 25. b 26. c 27. b 28. a 29. c 30. d
31. b 32. d 33. d 34. d 35. b 36. b 37. a 38. b 39. a 40. b
41. a 42. d 43. a 44. c 45. d 46. a 47. b 48. c 49. a 50. b
51. b 52. a 53. c 54. a 55. a 56. b 57. b 58. d 59. a 60. c
61. a 62. a 63. a 64. d 65. c 66. d 67. b 68. d 69. a 70. b
71. b 72. c 73. b 74. b 75. d 76. b 77. c 78. d 79. b 80. a
81. b 82. b 83. a 84. b 85. a 86. b 87. a 88. a 89. d 90. b
91. d 92. d 93. b 94. d 95. d 96. d 97. c 98. b 99. a 100. b

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Stereo Chemistry Assignment ( NET/GATE) 1

(I) (II) (III)

(a) (b) (c) (d)

9. What is the relation between shown compounds:

(a) Enantiomers. (b) Diastereomers. (c) Same. (d) None of these.

(a) Enantiomers. (b) Diastereomers. (c) Same. (d) Meso.

(a) (b) (c) (d)

(a) 3R, 6S (b) 3S, 6S (c) 3R, 6R (d) 3S, 6R

(a) Diastereomers. (b) Enantiomers. (c) Meso. (d) None of these.

17. The most stable conformation of the following compound is:

(a) (b) (c) (d)

(I) (II) (III)

(a) (b) (c) (d)

20. The compound in ‘R’ configuration is:

21. Draw the structure of (2R, 3S) – 2, 3 – dichloropentane

22. The most stable confirmation of following compound is:

(a) (b) (c) (d)

23. Structure of 1, 2-dimethylcyclohexane is show below. Which of the following is an enantiomer to

(a) (b) (c) (d)

24. Which is the most stable conformation of 1-chloro-4-methylcyclohexane?

(a) Diastereomers (b) Enantiomers (c) Both (d) None of these

28. The major product is formed in the following reaction is:

(a) 2 (b) 3 (c) 5 (d) 4

33. Consider the following statements:

(II) 2, 3-pentadiene is chiral and can exist as pair of enantiomers.

(III) 2, 3-pentadiene can exist as cis and trans-isomers.

(a) (b) (c) (d)

35. Draw the structure of (1 R, 2 S, 3 S)-1, 2-dibromo-3-ethyl cyclohexane:

(a) (b) (c) (d)

36. The molecule(s) that exist as meso structure(s) is/are:

(I) (II) (III)

(a) (b) (c) (d) All of these.

43. Which of the following structure represents meso compounds:

(a) (b) (c) (d) All of these.

44. The two compounds shown below are:

(a) Diastereomers (b) Epimers (c) Enantiomers (d) Regiomers

46. Methyl groups in the following compound are:

(a) Homotopic (b) Diasterotopic

(a) Configuration diastereomers (b) Enantiomers

(a) (b) (c) (d)

49. The correct statement about the following compound is:

(a) Compound is chiral and has P configuration.

(a) 5R,6R (b) 5R,6S (c) 5S,6R (d) 5S,6S

59. Among the following, the optically inactive compound is:

60. Bridge-head hydrogen of the conformer of cis-decalin is positioned as:

61. The binaphthol (Bnp) is:

(a) An optically active compound with (R)-configuration

The preferred conformations for the cis-and trans-compounds will be

(a) Ha, and Hb: enantiotopic (b) Ha, and Hb : diastereotopic

(I) (II) (III) (IV)

(X) (Y) (Z)

(a) X-homotopic, Y-enatiotopic and Z-diastereotopic

(a) 2Z, 4R (b) 2Z, 4S (c) 2E, 4R (d) 2E,4S

(a) R, S (b) S, R (c) R,R (d) S,S

(a) Two (b) Four (c) Six (d) Eight

71. The major product formed in the following reaction is:

(a) A is a single enantiomer. (b) A is a racemic mixture.

(A) (i) Chiral centre

(B) (ii) Chiral axis