(a)
Interpretation:
The complete, detailed mechanism for the given reaction is to be drawn and the product of the reaction is predicted.
Concept introduction:
A way to convert an alcohol into an
In the first step of the reaction, the oxygen atom of an alcohol is electron-rich and acts as a nucleophile, whereas the phosphorus atom in
Answer to Problem 10.3P
The complete and detailed mechanism for the given reaction is:
The product formed in given reaction and the overall reaction is:
Explanation of Solution
The given reaction is:
Deuterium is an isotope of hydrogen. Its chemical behavior is identical to hydrogen but serves as a label in reactions.
As a first step, the oxygen atom of an alcohol is electron-rich and acts as a nucleophile, whereas the phosphorus atom in
Note that, the stereochemical configuration of the carbon atom does not change at the end of this step.
In the second step, the chloride ion generated in the previous step acts as a nucleophile and the phosphorus-containing species acts as the substrate. The chloride ion attacks the carbon atom to which
Note that, though bromine is a good leaving group, but, since it is attached to the
When an alcohol is treated with
(b)
Interpretation:
The complete, detailed mechanism for the given reaction is to be drawn and the product of the reaction is predicted.
Concept introduction:
A way to convert an alcohol into an alkyl halide is to use phosphorus tribromide,
In the first step of the reaction, the oxygen atom of an alcohol is electron-rich and acts as a nucleophile, whereas the phosphorus atom in
Answer to Problem 10.3P
The complete and detailed mechanism for the given reaction is:
The product formed in given reaction and the overall reaction is:
Explanation of Solution
The given reaction is:
In the substrate above,
As a first step, the oxygen atom of an alcohol is electron-rich and acts as a nucleophile, whereas the phosphorus atom in
Note that, the stereochemical configuration of the carbon atom does not change at the end of this step as the carbon atom is not involved in this step.
In the second step, the bromide ion generated in the previous step acts as a nucleophile and the phosphorus containing species acts as the substrate. The bromide ion attacks the carbon atom to which
When an alcohol is treated with
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Chapter 10 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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