Test 3: Disubstituted Cycloalkanes

Since these molecules come up often in exams, it’s a good idea to just memorize a few simple rules for them. 

Cis-1,2-Disubstituted Cyclohexane

Because cyclohexane has axial and equatorial positions, some professors will have different definitions of whether this is chiral or not.

  • Textbook Answer (I agree with this one) = Achiral
  • Some wacky professors = Chiral due to axial/equatorial positions.

Note: I’ve had an Organic Chemist from Yale argue with me that it was chiral. So just check with your prof!

Example: Using TEST 3, is the following molecule chiral?

1m

Example: Using TEST 3, is the following molecule chiral?

1m

Example: Using TEST 3, is the following molecule chiral?

1m

Example: Using TEST 3, is the following molecule chiral?

2m