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How can you decide whether an observed rotation of a solution of an optically active compound is +180° or -180°.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter3: Stereoisomerism And Chirality

Section3.7: Optical Activity—how Chirality Is Detected In The Laboratory

Problem 3.9P

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Concept explainers

Stereochemistry and Isomerism

Stereochemistry deals with the three-dimensional structure and properties of molecules. It explains the arrangement of atoms and their manipulation within a molecule in a 3D structure. Stereochemistry can be dealt with all types of molecules. Based on the stereochemistry of a molecule, the physical and chemical properties of the molecules vary.

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How can you decide whether an observed rotation of a solution of an optically active
compound is +180° or -180°.

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1. When 0.247 g of monosodium glutamate (MSG) is dissolved in 10.0 mL of water and placed in a sample cell 10.0 cm in length, the observed rotation at 20°(using the D line of sodium) is +0.632°. Calculate the specific rotation of MSG. 2. When 0.095 g of cholesterol is dissolved in 1.00 mL of ether and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is -0.299°.Calculate the specific rotation of cholesterol.3. The specific rotation of L-dopa in water (at 15°C) is -39.5. A chemist prepared a mixture of L-dopa and its enantiomer, and this mixture had a specific rotation of -34. Calculate the % ee of this mixture. 4. The specific rotation of vitamin B7 in water (at 22°C) is +92. A chemist prepared a mixture of vitamin B7 and its enantiomer, and this mixture had a specific rotation of +18. Calculate the % ee of this mixture.
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