Draw the neutral organic starting material. Br, CH,CI, Br

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
Chapter6: Reactions Of Alkenes
Section6.3: Electrophilic Additions
Problem 6.2P: Name and draw a structural formula for the product of each alkene addition reaction. (a) (b)
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Draw the neutral organic starting material.

The Hint: The reaction conditions support electrophilic addition of Br2 to an alkene's C=C double bond, which would normally yield a dibromo product. However, the product has only one bromine atom, with a C–O bond on the adjacent carbon. This fragment is diagnostic for a halohydrin, where an oxygen nucleophile (water or alcohol) reacts with a bromonium intermediate to generate the O–CH2CH2–Br motif. Work backwards to determine what the starting material must look like. There should be an alcohol and an alkene in the neutral organic starting material.

Draw the neutral organic starting material.
Br,
CH,CI,
Br
Transcribed Image Text:Draw the neutral organic starting material. Br, CH,CI, Br
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