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Stereochemistry of the Addition of Bromine to Trans-Cinnamic Acid

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The question is attached and here are the Directions:

Based on the mechanism present, predict the product of this reaction.
Highlight the Br-C-C-Br dihedral angle.
Is the diehdral angle (0 degrees for sin addition or 180 degrees for anti addition)?
Look at the dihedral angle between the phenyl ring and the carboxylic acid group. Does this correlate to the trans-cinnamic acid starting material?
Repeat this process for the other diastereomer.

Please inclue structures (with sterochemistry labeled).

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Solution Summary

Word document attached shows how to make these two chiral centres that are enantiomers of each other.

Similar Posting

Predict stereochemistry of product and mechanism of reaction

Questions to answer:

1. Determine the stereochemistry of the product and propose a mechanism for the reaction.

2. From the melting point of the product, decide whether the the addition of bromine followed a syn or anti mechanism? Why?

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