Chapter 4, Problem 4.60P

Interpretation Introduction

(a)

Interpretation:

For each of the given molecule, the correct dash-wedge structure is to be drawn.

Concept introduction:

In Newman projection, the two atoms directly connected by the bond of interest are shown clearly. The nearer atom is represented as a point, and the more distant atom is represented as a circle. Bonds to the front atom meet at the point whereas bonds to the back atom connect to the circle.

Interpretation Introduction

(b)

Interpretation:

For each of the given molecule, the corresponding Haworth projection is to be drawn.

Concept introduction:

While drawing Haworth projection, the relationship of each substituent to the plane of the ring needs to be considered. In a Haworth projection, the ring is represented as being planar, and bonds to substituents are drawn perpendicular to that plane.

Interpretation Introduction

(c)

Interpretation:

It is to be determined, for each given molecule, whether the given conformation is most stable.

Concept introduction:

Each substituent on a cyclohexane ring is more stable in an equatorial position than in an axial position. More space is available on equatorial position than axial position. Therefore, the diequatorial conformer is more favorable over the diaxial conformer.

Interpretation Introduction

(d)

Interpretation:

For the given each molecule, the Newman projection of the molecule whose conformation is not the most stable conformation, is to be drawn.

Concept introduction:

Each substituent on a cyclohexane ring is more stable in an equatorial position than in an axial position. More space is available on equatorial position than axial position. Therefore, the diequatorial conformer is more favorable over the diaxial conformer.