lz explain why in part 6, this isnt suitable for E2

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
Section: Chapter Questions
Problem 6.15P
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plz explain why in part 6, this isnt suitable for E2

Part 5:
Choose the most appropriate reagent(s) for the first step of the synthesis.
H3C
CH3
A
C
E
CH3
A
C
E
HBr
reagent(s)
Br₂, H₂O
OH
H₂O, H₂SO4
HCI
This will add Br to the more highly-substituted carbon of the alkene and hydrogen to the less-substituted
carbon. (Markovnikov addition of HBr).
Part 6:
Choose the most appropriate reagent(s) for the second step of the synthesis.
H3C
Br
OH
1. Mg, ether
2. H₂O
B
HBr
D
CH3CH₂OK, CH3CH₂OH
CH3
HBr, H₂O
Br
Br2, CC14
reagent(s)
CH3
B tBuOK, tBuOH
D H₂O, H₂SO4
This reagent will promote E2 elimination resulting in predominantly the most stable alkene isomer.
Transcribed Image Text:Part 5: Choose the most appropriate reagent(s) for the first step of the synthesis. H3C CH3 A C E CH3 A C E HBr reagent(s) Br₂, H₂O OH H₂O, H₂SO4 HCI This will add Br to the more highly-substituted carbon of the alkene and hydrogen to the less-substituted carbon. (Markovnikov addition of HBr). Part 6: Choose the most appropriate reagent(s) for the second step of the synthesis. H3C Br OH 1. Mg, ether 2. H₂O B HBr D CH3CH₂OK, CH3CH₂OH CH3 HBr, H₂O Br Br2, CC14 reagent(s) CH3 B tBuOK, tBuOH D H₂O, H₂SO4 This reagent will promote E2 elimination resulting in predominantly the most stable alkene isomer.
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