QuestionStereochemistry / symmetry elements
Which one of the following molecules does NOT have a plane of symmetry?

- (a) 3,4-Dichlorohexane (sawhorse form)
- (b) 3,4-Dichlorohexane (zigzag, both Cl wedged)
- (c) 1,3-Dichlorocyclobutane (one Cl wedge, one dash)
- (d) 1,2,3-Trimethylcyclopropane (one Me dash, two wedged)
Answer: (b)
(b) 3,4-dichlorohexane as drawn is (3S,4S) — a chiral (dl) form, so it has no plane of symmetry. (a) is the meso form, (c) trans-1,3-dichlorocyclobutane and (d) the trimethylcyclopropane have a mirror plane → (b).