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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Students have asked these similar questions
An aqueous solution containing 10 g of an optically pure compound was diluted to 500 mL with water and was found to have a specific rotation of −121º. If this solution were mixed with 500 mL of a solution containing 3 g of a racemic mixture of the compound, what would the specific rotation of the resulting mixture of the compound? What would be its optical purity?
The specific rotation for (-)-methylphenidate is -38° mL g¹ dm¯1. Path length of the polarimeter is 1 dm. 1 You dissolve 0.5 g of a mixture of (-)-methylphenidate and its enantiomer in 4 mL of water. You place the sample into a polarimeter and the observed rotation is found to be -0.2°. What percent of the mixture is composed of (-)- methylphenidate? (Round your answer to the nearest whole percent.) The numerical values in this calculation will change with each attempt. Double check before submitting additional attempts. 17
An enantiopure naturally occurring sugar had a specific rotation of +136. A synthetic sample of this sugar gave a rotation of +84°, when a sample of concentration 1.37 g/100 ml was placed in a cell with a path length of 20 cm. (i) Which of the following prefixes could be used to describe this compound (on the basis of the information provided) +/-, d/l, D/L, R/S? (ii) Calculate the ee of the synthetic sample.
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