Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
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Chapter 5.4, Problem 16ATS
Interpretation Introduction

Interpretation:

To calculate the observed rotation of given molecules.

Concept Introduction:

Observed rotation: The sample of a compound is the angle by which it rotates the plane of polarized light, measured using the polarimeter. Further observed rotation of a sample of a compound depends on the concentration if a solution is used for the experiment (or) density of the sample is neat.

The observed rotation of a molecule can be calculated by using the formula given below.

[α]=αc×lα=[α]×c×l

alpha (α) represents the observed rotation measured with a polarimeter. l represents the length of the sample tube.     C is the concentration of a solution of a pure sample.

To identify: The given molecules observed rotation should be identified.

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2. Please consider the two all 'cis' isomers of trimethylcyclohexane drawn below. Draw the two chair conformers of each stereoisomer below (1 and 2) and calculate their torsional interaction energies in order to identify the lower energy conformer for each stereoisomer. Based on your calculations, state which of the two stereoisomers 1 and 2 is less stable and which is more stable. [1,3-diaxial CH3 CH3 = 3.7kcal/mol; 1,3-diaxial CH3 H = 0.88kcal/mol; cis-1,2 (axial:equatorial) CH3 CH3 = 0.88kcal/mol; trans-1,2-diequatorial CH3 CH3 = 0.88kcal/mol) all-cis-1,2,3- 1 all-cis-1,2,4- 2
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