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explain any differences or similarities in the stereochemistry of the bromine addition reactions of trans-cinnamic acid...

explain any differences or similarities in the stereochemistry of the bromine addition reactions of trans-cinnamic acid and trans-anethole.

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Answer #1

Bromine addition to trans-cinnamic acid and trans-anethole takes place via the formation of cyclic bromonium ion. The mechanism for both the reactions are given below. We observe that in the case of trans cinnamic acid, Br- does backside attack on the cyclic bromonium ion in the second step forming a anti product while in case of trans anethole OCH3 stabalises the cyclic bromonium ion thus favouring both frontside and backside attack of Br- in the second step and we get both syn and anti products.

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