Examination of Trans-Cinnamic Acid

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Examination of Trans-Cinnamic Acid

The Stereochemistry of Bromine Addition: Bromination of trans-Cinnamic Acid Pitak Chuawong Objectives 1. To perform bromination of trans-‐cinnamic acid 2. To investigate stereochemistry of bromination reaction Introduction Alkenes undergo electrophilic addition to give alkyl halides. When bromine is used as a reagent, the reaction proceeds via 2-‐step process. The first step involves the formation of bridged bromonium ion followed by the nucleophilc attack by bromide ion to give vicinal dibromide. The stereochemistry of this reaction is said to be “anti-‐addition.”

H Br Br Br Br H Br Br

anti-addition

In general, when trans-‐cinnamic acid is used as a reactant, two enantiomeric pairs can be formed, one from anti-‐addition and the other from syn-‐addition. The chemical reactions as well as the products’ Fischer projections are elucidated here.

O OH trans-cinnamic acid Note: = reflux Br2 in CH2Cl2 Br 2,3-dibromo-3-phenylpropanoic acid Br O OH

CO2H H Br Br H Ph 2S,3S

CO2H Br H H Br Ph 2R,3R

CO2H Br H Br H Ph 2R,3S

H H

CO2H Br Br Ph

2S,3R

Enantiomeric pair (threo) mp = 93.5-95 oC Another enantiomeric pair (erythro) mp = 202-204 oC Ph = Phenyl group

In this experiment, you will brominates trans-‐cinnamic acid and determine the stereochemistry of the product by means of

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