Chapter 4, Problem 50PP

Interpretation Introduction

Interpretation:

Chair conformations of menthol should be drawn and least energetic conformer is needed to be predicted between them.

Concept introduction:

Chair conformer: chair conformer is a stable conformer for cyclohexane compound. in this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.

Example:

After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.

Stereochemistry conversions in chair conformation are shown below.

Substituent position	cis	trans
1,2 position	(a,e) or (e,a)	(a,a) or (e,e)
1,3 position	(a,a) or (e,e)	(a,e) or (e,a)
1,4 position	(a,e) or (e,a)	(a,a) or (e,e)

To find: chair conformer of the menthol molecule.