Show how you would prepare 4-deuterio toluene from toluene.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
Problem 11E
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Solvent choice:
When we write reactions on paper, we usually specify a solvent that is commonly used
for the particular reaction. However, until we go into the laboratory and try the reactions,
the solvent effects will not be entirely known. In the case of a Grignard reaction, we need
to choose a solvent that will not react with the highly reactive reagent. Of course, any
protic solvent such as water or alcohols or acetic acid are unacceptable as they will
destroy the Grignard reagent through protonation.
Although we generally do not wish to destroy our Grignard reagent, this protonation by
water can be used to specifically label molecules with isotopes such as deuterium or
tritium. Show how you would prepare 4-deuterio toluene from toluene.
Transcribed Image Text:Solvent choice: When we write reactions on paper, we usually specify a solvent that is commonly used for the particular reaction. However, until we go into the laboratory and try the reactions, the solvent effects will not be entirely known. In the case of a Grignard reaction, we need to choose a solvent that will not react with the highly reactive reagent. Of course, any protic solvent such as water or alcohols or acetic acid are unacceptable as they will destroy the Grignard reagent through protonation. Although we generally do not wish to destroy our Grignard reagent, this protonation by water can be used to specifically label molecules with isotopes such as deuterium or tritium. Show how you would prepare 4-deuterio toluene from toluene.
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