EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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?
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.
CH, CH, Q3: The specific rotation of L-alanine in water (at 25°C) is +2.8. A chemist prepared a mixture of L-alanine and its enantiomer, and 3.50 g of the mixture was dissolved in 10.0 mL of water. This solution was then placed in a sample cell with a pathlength of 10.0 cm and the observed rotation was +0.78. Calculate the % ee of the mixture.
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