Write the product of the two reactions shown below. In the first step indicate if the product is meso or is formed as a racemic mixture. Indicate whether final structure in the second reaction is cis or trans. Br-Br H LDA, THF solvent

Write the product of the two reactions shown below. In the first step indicate if the product is meso or is formed as a racemic mixture. Indicate whether final structure in the second reaction is cis or trans. Br-Br H LDA, THF solvent

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section24.4: Catalytic Allylic Alkylation

Problem 24.3P

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Question

Write the product of the two reactions shown below. In the first step indicate if the product
is meso or is formed as a racemic mixture. Indicate whether final structure in the second
reaction is cis or trans.
Ph
Br-Br
H.
LDA,
THF solvent
|

Expert Solution

Step 1

Br₂ adds to an alkene in an anti manner. The reaction proceeds by the formation of bromonium ion. In case of cis alkene, both cis and trans products are formed.

LDA is used to abstract the H⁺ resulting in the formation of alkene.

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