Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
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Chapter 6, Problem 6.11P
Interpretation Introduction

(a)

Interpretation:

The line-and-wedge formula of (S)-(+)-ibuprofen is to be drawn.

Concept introduction:

The naming of the chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chiral center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The specific rotation of pure (S)-(+)-ibuprofen and pure (R)-()-ibuprofen is to be calculated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. It rotates the plane of a plane polarized light. The enantiomeric excess of a sample is given as,

EE=100%×[α]mixture[α]pure

Interpretation Introduction

(c)

Interpretation:

The percentage of each enantiomer present in the given sample is to be calculated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. It rotates the plane of a plane polarized light. The enantiomeric excess of a sample is given as,

EE=100%×[α]mixture[α]pure

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A solution of 0.50 g of (-)@epinephrine dissolved in 10.0 mL of diluteaqueous HCl was placed in a 20-cm polarimeter tube. Using the sodium D line, the rotation was found to be -5.1° at 25 °C. Determine the specific rotation of epinephrine.
When 0.075g of penicillamine is dissolved in 10.0 mL of pyridine and placed in a sample cell 10.0 cm in length, the observed rotation at 20 degrees (using the D line of sodium) is -0.47 degrees. Calculate the specific rotation of penicillamine. a. (-0.47)/[(0.075g/mL) (1.00 dm)]= -6.3 b.   (0.47)/[(0.075g/mL) (1.00 dm)]= 6.3 c.  (-0.47)/[(0.0075g/mL) (1.00 dm)]= -63 d. (0.47)/[(0.0075g/mL) (1.00 dm)]= 63
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