1,2-shift R [1] `H + H,ö: HÖ 1° alcohol no 1° carbocation 2° carbocation at this step OH H2SO4 [2]

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
Section11.8: The E2 Reaction And The Deuterium Isotope Effect
Problem 17P
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Rearrangements can occur during the dehydration of 1° alcohols even
though no 1° carbocation is formed—that is, a 1,2-shift occurs as the C—
OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as
shown in Equation [1]. Using this information, draw a stepwise
mechanism for the reaction shown in Equation [2]. We will see another
example of this type of rearrangement

1,2-shift
R
[1]
`H + H,ö:
HÖ
1° alcohol
no 1° carbocation
2° carbocation
at this step
OH
H2SO4
[2]
Transcribed Image Text:1,2-shift R [1] `H + H,ö: HÖ 1° alcohol no 1° carbocation 2° carbocation at this step OH H2SO4 [2]
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