Consider the addition of HBr shown here. HBr (a) There are three carbocation intermediates possible from the protonation of this triene. Draw all three of them and identify the most stable one. (b) Draw all halogenated products formed by attack of Br on the most stable carbocation. (c) Which of those products would you expect to be formed in the greatest amount at low temperatures? (d) Which would you expect to be formed in the greatest amount at high temperatures?

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
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.31P
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Consider the addition of HBr shown here.
HBr
(a) There are three carbocation intermediates possible
from the protonation of this triene. Draw all three of
them and identify the most stable one.
(b) Draw all halogenated products formed by attack of Br on the most stable carbocation.
(c) Which of those products would you expect to be formed in the greatest amount at low temperatures?
(d) Which would you expect to be formed in the greatest amount at high temperatures?
Transcribed Image Text:Consider the addition of HBr shown here. HBr (a) There are three carbocation intermediates possible from the protonation of this triene. Draw all three of them and identify the most stable one. (b) Draw all halogenated products formed by attack of Br on the most stable carbocation. (c) Which of those products would you expect to be formed in the greatest amount at low temperatures? (d) Which would you expect to be formed in the greatest amount at high temperatures?
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