Which of the following molecules is expected to rotate the plane of plane polarized light?
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
A molecule turns the plane of polarised light only when it is chiral, which here means it carries a carbon bonded to four different groups and has no internal mirror plane. Three of the structures possess a plane of symmetry and so are optically inactive in spite of their substitution. The remaining one has a genuine stereocentre with four distinct groups, and that is the molecule able to rotate the plane of polarisation.
JEE Main · 2007 · 29 Apr 2007 · Offline · Single correct option