During the workup portion of the reaction of alkenes with HBr as described in the experiment provided, a student transferred the reaction mixture to a separatory funnel, rinsed the reaction flask with diethyl ether, and added the ether rinses to the separatory funnel.  The student then added sodium bicarbonate to the separatory funnel. Extremely vigorous bubbling occurred.  What did the student do wrong?  Can they still isolate the product?  If so describe the next steps the student should take to isolate the product.

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
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.22P: Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h...
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During the workup portion of the reaction of alkenes with HBr as described in the experiment provided, a student transferred the reaction mixture to a separatory funnel, rinsed the reaction flask with diethyl ether, and added the ether rinses to the separatory funnel.  The student then added sodium bicarbonate to the separatory funnel. Extremely vigorous bubbling occurred.  What did the student do wrong?  Can they still isolate the product?  If so describe the next steps the student should take to isolate the product.

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