Grignard reagents cannot be generated in the presence of an alcohol, as the acidic hydrogen will quench the Grignard reagent as it is formed. Choose the appropriate protecting group, then draw the expected intermediates (with the protecting group drawn out) and final product in this sequence. All structures should be neutral; omit byproducts. Br OH reagent 1 product 1 Mg ether

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
Section: Chapter Questions
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Identify Reagent 1, and draw product 1, 2, 3, 4

Grignard reagents cannot be generated in the presence of an alcohol, as the acidic hydrogen will quench the Grignard reagent as
it is formed. Choose the appropriate protecting group, then draw the expected intermediates (with the protecting group drawn
out) and final product in this sequence. All structures should be neutral; omit byproducts.
Br
product 4
Major product only;
omit the protecting group
Identify reagent 1.
ethylene glycol
TBDMS-CI
MOM-C1
OH
Bu₂N*F-
reagent 1
product 3
product 1
1. acetone
2. H₂O, H*
Mg
ether
product 2
Transcribed Image Text:Grignard reagents cannot be generated in the presence of an alcohol, as the acidic hydrogen will quench the Grignard reagent as it is formed. Choose the appropriate protecting group, then draw the expected intermediates (with the protecting group drawn out) and final product in this sequence. All structures should be neutral; omit byproducts. Br product 4 Major product only; omit the protecting group Identify reagent 1. ethylene glycol TBDMS-CI MOM-C1 OH Bu₂N*F- reagent 1 product 3 product 1 1. acetone 2. H₂O, H* Mg ether product 2
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