Answer to self-test question #4

a) The tert- butyl group locks the cyclohexane ring into one particular chair conformation,i.e., the one shown in the problem. In order to be anti-periplanar to an adjacent (also axial) hydrogen, the leaving group must be in the axial position. This is impossible for the trans compound.


Hit the Back button on the Netscape toolbar to return to the main page.