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Magazine Chapter 20: Q-5-21P (page 1038)
Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.
(a) meso-2,3-dibromo-2,3-dichlorobutane
(b) -2,3-dibromo-2,3-dichlorobutane
(c) (2R,3S)-2-bromo-3-chlorobutane
(d) (2R,3S)-2,3-dibromobutane
(e) (R,R)-2,3-dibromobutane
(f)
(g)
(h)
Short Answer
(a). It is not a chiral compound.
(b). It is a chiral compound.
(c). It is a chiral compound.
(d). It is not a chiral compound.
(e). It is a chiral compound.
(f). It is a chiral compound.
(g). It is not a chirtal compound.
(h). It is a chiral compound.
Step by step solution
Pointing out the chiral carbon and show in fischer projection formula.
(a)
Though it have two chiral carbons but due to presence of plane of symmetry this compound is achiral and meso compound so no mirror image relationship.
(b)
This compound is optically active and it contains two chiral centers and this compound gives a mirror image relationship, which is not superimposable.
(c)
This compound have two chiral centers and it gives mirror image relationship which is chiral and is not superimposable.
(d)
(e
This compound is optically active giving mirror image relationship and they are not superimposable to each other and contains two chiral centers.
(f)
This compound is optically active, and this compound gives a mirror image relationship and is non-superimposable.
(g)
This compound contains a plane symmetry and so achiral and optically inactive.
(h)
The compound does not contain any symmetry elements so it is chiral and optically active compound.
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