Treating 1,3-butadiene with 1 mole of HBr gives a mixture of two isomeric products. Br CH2=CH-CH=CH, + H-Br - CH,— CH—CH— CH, + CH,—Сн— СН—CH, — Вr 1,3-Butadiene 3-Bromo-1-butene 1-Bromo-2-butene (a racemic mixture) Propose a mechanism that accounts for the formation of these two products.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
Section11.SE: Something Extra
Problem 34MP: Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the...
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Treating 1,3-butadiene with 1 mole of HBr gives a mixture of two isomeric products.
Br
CH2=CH-CH=CH, + H-Br -
CH,— CH—CH— CH, + CH,—Сн— СН—CH, — Вr
1,3-Butadiene
3-Bromo-1-butene
1-Bromo-2-butene
(a racemic mixture)
Propose a mechanism that accounts for the formation of these two products.
Transcribed Image Text:Treating 1,3-butadiene with 1 mole of HBr gives a mixture of two isomeric products. Br CH2=CH-CH=CH, + H-Br - CH,— CH—CH— CH, + CH,—Сн— СН—CH, — Вr 1,3-Butadiene 3-Bromo-1-butene 1-Bromo-2-butene (a racemic mixture) Propose a mechanism that accounts for the formation of these two products.
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