Does dehydrogenation of alkyl halides create Zaitsef or Hoffman products? In this example, which is created? I think it's Hoffman because there is a more stable/substituted option which is to put the double bond to the right of the positive charge instead of to the left. Or does it depend on the reactants? Further clarification is needed.  Thank you in advance!

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
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Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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Does dehydrogenation of alkyl halides create Zaitsef or Hoffman products? In this example, which is created? I think it's Hoffman because there is a more stable/substituted option which is to put the double bond to the right of the positive charge instead of to the left.

Or does it depend on the reactants? Further clarification is needed. 

Thank you in advance!

Dehydrogenation of Alkyl Halides (strong/weak base):
alkyl halide to alkene
Elimination of a proton and halide ion; alkyl halide into alkene.
E1:
H CH₂CH3
H-C-
-C-CH₂CH3
CH3 Br:
E2:
Na+ CH₂0
H
H-C
CH₂CH3
-C-CH₂CH3
12
CH₂ :Br:
CH₂OH
Na+ -OCH3
CH₂OH
H CH₂CH3
H-C-C-CH₂CH₂
CH3
Br:
carbocation intermediate
CH₂0-H
H
H₂C
Na+
Br:
CH₂CH3
CH₂CH3
CH₂OH
H
H₂C
+..
CH3- -0
H
no intermediate
CH₂CH3
CH₂CH3
-H :Br:¯
Transcribed Image Text:Dehydrogenation of Alkyl Halides (strong/weak base): alkyl halide to alkene Elimination of a proton and halide ion; alkyl halide into alkene. E1: H CH₂CH3 H-C- -C-CH₂CH3 CH3 Br: E2: Na+ CH₂0 H H-C CH₂CH3 -C-CH₂CH3 12 CH₂ :Br: CH₂OH Na+ -OCH3 CH₂OH H CH₂CH3 H-C-C-CH₂CH₂ CH3 Br: carbocation intermediate CH₂0-H H H₂C Na+ Br: CH₂CH3 CH₂CH3 CH₂OH H H₂C +.. CH3- -0 H no intermediate CH₂CH3 CH₂CH3 -H :Br:¯
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