The reaction scheme below, proposed by students, will not work. Why not? HO -Br OH Mg HO -MgBr ether 1. cyclohexanone 2. mild H3O+ HO O The Grignard reagent will immediately react with the phenolic OH group, destroying the Grignard reagent before it can react with cyclohexanone. O The H30+ in the second step will destroy the erignard Reagent. O The H3O+ in the second step needs to be strong acid, because the Grignard reagent is a strong base. O Cyclohexanone is too sterically congested.

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The reaction scheme below, proposed by students, will not work. Why not?
HO
-Br
OH
Mg
HO
-MgBr
ether
1. cyclohexanone
2. mild H3O+
HO
O The Grignard reagent will immediately react with the phenolic OH group, destroying the Grignard reagent before it can react with cyclohexanone.
O The H30+ in the second step will destroy the erignard Reagent.
O The H3O+ in the second step needs to be strong acid, because the Grignard reagent is a strong base.
O Cyclohexanone is too sterically congested.
Transcribed Image Text:The reaction scheme below, proposed by students, will not work. Why not? HO -Br OH Mg HO -MgBr ether 1. cyclohexanone 2. mild H3O+ HO O The Grignard reagent will immediately react with the phenolic OH group, destroying the Grignard reagent before it can react with cyclohexanone. O The H30+ in the second step will destroy the erignard Reagent. O The H3O+ in the second step needs to be strong acid, because the Grignard reagent is a strong base. O Cyclohexanone is too sterically congested.
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