(a) Interpretation: Whether the form of the fischer projection of the molecule is D or L is to be identified and the structure of the enantiomer is to be drawn. Concept introduction: The D (dextrorotatory) and L (laevorotatory) isomers are mirror images of each other and are known as enantiomers. The enantiomers which have the property of rotating the plane polarized light to the left are laevorotatory and those which rotate the plane polarized light to the right are dextrorotatory. Therefore, the characteristic physical property of optically active molecules is rotating plane polarized light.

Question

Kumada Coupling: 1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a mechanism and give two reasons why you would NOT get the desired product. Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene. Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Answer 1

Question

Chapter 17, Problem 17.12E

Interpretation Introduction

(a)

Interpretation:

Whether the form of the fischer projection of the molecule is D or L is to be identified and the structure of the enantiomer is to be drawn.

Concept introduction:

The D (dextrorotatory) and L (laevorotatory) isomers are mirror images of each other and are known as enantiomers. The enantiomers which have the property of rotating the plane polarized light to the left are laevorotatory and those which rotate the plane polarized light to the right are dextrorotatory. Therefore, the characteristic physical property of optically active molecules is rotating plane polarized light.

Interpretation Introduction

(b)

Interpretation:

Whether the form of the fischer projection of the molecule is D or L is to be identified and the structure of the enantiomer is to be drawn.

Concept introduction:

The D (dextrorotatory) and L (laevorotatory) isomers are mirror images of each other and are known as enantiomers. The enantiomers which have the property of rotating the plane polarized light to the left are laevorotatory and those which rotate the plane polarized light to the right are dextrorotatory. Therefore, the characteristic physical property of optically active molecules is rotating plane polarized light.

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