Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 2, Problem 2.3P
Interpretation Introduction

(a)

Interpretation:

The Newman projection for each staggered and eclipsed conformation about the C2C3 bond of isopentane is to be drawn. All staggered and eclipsed conformations of isopentane are to be shown.

Concept introduction:

Newman projections are drawn to visualize the different conformations of a compound around CC bond. In Newman projection, the circle represents the back carbon and the dot represents the front carbon. The potential energy diagram of the eclipsed form is higher than that of staggered form.

Interpretation Introduction

(b)

Interpretation:

The curve of potential energy versus dihedral angle for all conformation of isopentane about C2C3 is to be sketched. The energy maximum and minimum for each conformation are to be labeled.

Concept introduction:

Newman projections are drawn to visualize the different conformations of a compound around CC bond. In Newman projection, the circle represents the back carbon and the dot represents the front carbon. The potential energy diagram of the eclipsed form is higher than that of staggered form.

Interpretation Introduction

(c)

Interpretation:

The conformations out of all conformations of isopentane about C2C3 that are likely to be present in a great amount in the sample of isopentane are to be identified. The explanation for the corresponding answer is to be stated.

Concept introduction:

Newman projections are drawn to visualize the different conformations of a compound around CC bond. In Newman projection, the circle represents the back carbon and the dot represents the front carbon. The potential energy diagram of the eclipsed form is higher than that of staggered form.

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For 1,2-dichloroethane: (a) Draw Newman projections for all eclipsed conformations formed by rotation from 0 to 360° about the carbon-carbon single bond. (b) Which eclipsed conformation(s) has the lowest energy? Which has the highest energy? (c) Which, if any, of these eclipsed conformations are related by reflection?
4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4- Dibromocyclohexane. 4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-Dibromocyclohexane. 4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4- Dibromolcyclohexane. Explain the reason for your choice.
(c)Conformational isomer is the different spatial arrangement of the atoms that resulted from rotation about a single bond. (i) Differentiate anti conformers and gauche conformers (ii) Using a newman projection, draw the anti conformer and gauche conformers of 3,3-dimethylheptane (viewed along the C3-C4 bond)
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