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Chapter 4: Q. 4-4-12P (page 104)

Draw two different chair conformations of cyclohexanol (hydroxycyclohexane),showing all hydrogen atoms. Identify each position as axial orequatorial.

Short Answer

Expert verified

The two different chair conformations of cyclohexanol are:

Step by step solution

01

Chair confirmation

Chair conformation structure for a six-membered ring is when atoms 2, 3, 5, and 6 lie in the same plane, atom one lies above the plane, and atom 4 lies below the plane.

02

Axial and equatorial positions:

Axial bonds are the bonds that are perpendicular or vertical to the ring plane. Equatorial bonds are approximately horizontal in the plane of the ring.

03

Structure of cyclohexanol: Axial

The hydroxyl group and five hydrogens present here are perpendicular or vertical to the ring plane.

The bond in pink represents axial bonds

04

Structure of cyclohexanol: Equatorial

Here hydroxyl group and five hydrogens are present approximately horizontal in the plane of the ring.

The bond in pink represents Equatorial bonds

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Most popular questions from this chapter

Why do you suppose an axial cyano (–CN) substituent causes practically no 1,3-diaxial steric strain (0.4 kJ/mol)? Use molecular models to help with your answer.

A trisubstituted cyclohexane with three substituents—red, green, and blue—undergoes a ring-flip to its alternate chair conformation. Identify each substituent as axial or equatorial, and show the positions occupied by the three substituents in the ring-flipped form.

Look at the following structure of the female hormone estrone, and tell whether each of the two indicated ring-fusions is cis or trans.

Name the following cycloalkane

Draw the structures of the following molecules:

(a) trans-1-Bromo-3-methylcyclohexane

(b) cis-1,2-Dimethylcyclobutane

(c) trans-1-tert-Butyl-2-ethylcyclohexane
See all solutions

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