Q10 · CSIR-NET Chemistry, December 2013
Paper: CSIR-NET December 2013 · Subject: Organic Chemistry · Chapter: General Organic Chemistry · Topic: Stereochemistry R S E Z · Marks: 2 · Difficulty: Medium
The correct statement about the following molecule is 
(a)Molecular is chiral and possesses a chiral plane
(b)Molecule is chiral and possesses a chiral axis.
(c)Molecule is achiral as it possesses a plane of symmetry.
(d)Molecule is achiral as it possesses a centre of symmetry.
Answer
Answer (as printed): A
Explanation
The molecule is a [2.2]paracyclophane with two Br atoms on one deck, para to each other (one on each side of the ring). The only symmetry element is a C₂ axis through the two ring centres; there is no mirror plane and no centre of symmetry, because the second deck rules them out. The molecule is therefore chiral, and its chirality element is a chiral plane (the substituted benzene deck), so this is planar chirality (a).
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