Concept explainers
(a)
Interpretation:
The complete, detailed mechanism for the reaction is to be provided. The stereochemistry of the products is to be predicted where appropriate. If the reaction yields exclusively one product or a mixture of products, then the major product is to be determined.
Concept introduction:
For the prediction of the outcome of the

Answer to Problem 9.64P
The complete, detailed mechanism for the reaction is shown below:
Explanation of Solution
The given reaction is
The absolute configuration of the substrate is S. This is solvolysis reaction because ethanol acts as a nucleophile and a solvent. The leaving group,
The attacking species
The loss of the leaving group,
A tertiary carbocation is highest stability than a secondary and primary carbocation. Next,
Now, the weak nucleophile,
Finally, deprotonation of the
The detailed, complete mechanism is as follows:
The outcome of the given reaction is predicted by considering factors like the nature of the leaving group, substrate, the strength of the reagent used, solvent, and temperature.
(b)
Interpretation:
The complete, detailed mechanism for the reaction is to be provided. The stereochemistry of the products is to be predicted where appropriate. If the reaction yields exclusively one product or a mixture of products, then the major product is to be determined.
Concept introduction:
For the prediction of the outcome of the

Answer to Problem 9.64P
The complete, detailed mechanism for the reaction is shown below:
The stereochemistry of the product is R configuration.
Explanation of Solution
The given reaction is
The absolute configuration of the substrate is S. The leaving group,
The attacking species
The carbon atom attached to the leaving group is a chiral center.
The stereochemistry of the product is R configuration.
The outcome of the given reaction is predicted by considering factors like the nature of the leaving group, substrate, the strength of the reagent used, solvent, and temperature.
(c)
Interpretation:
The complete, detailed mechanism for the reaction is to be provided. The stereochemistry of the products is to be predicted where appropriate. If the reaction yields exclusively one product or a mixture of products, then the major product is to be determined.
Concept introduction:
For the prediction of the outcome of the

Answer to Problem 9.64P
The complete, detailed mechanism for the reaction is shown below:
Explanation of Solution
The given reaction is
The absolute configuration of the substrate is S. The leaving group,
The attacking species
In the substrate, the alpha C atom has one H atom attached to it. Since
The outcome of the given reaction is predicted by considering factors like the nature of the leaving group, substrate, the strength of the reagent used, solvent, and temperature.
(d)
Interpretation:
The complete, detailed mechanism for the reaction is to be provided. The stereochemistry of the products is to be predicted where appropriate. If the reaction yields exclusively one product or a mixture of products, then the major product is to be determined.
Concept introduction:
For the prediction of the outcome of the

Answer to Problem 9.64P
The complete, detailed mechanism for the reaction is shown below:
Explanation of Solution
The given reaction is
The absolute configuration of the substrate is S. The leaving group,
The attacking species
The loss of the leaving group,
A tertiary carbocation is greatest stability than a secondary and primary carbocation. Next,
Now, the weak nucleophile
The detailed, complete mechanism is as follows:
The outcome of the given reaction is predicted by considering factors like the nature of the leaving group, substrate, the strength of the reagent used, solvent, and temperature.
(e)
Interpretation:
The complete, detailed mechanism for the reaction is to be provided. The stereochemistry of the products is to be predicted where appropriate. If the reaction yields exclusively one product or a mixture of products, then the major product is to be determined.
Concept introduction:
For the prediction of the outcome of the

Answer to Problem 9.64P
The complete, detailed mechanism for the reaction is shown below:
Explanation of Solution
The given reaction is
This is a solvolysis reaction because ethanol acts as a nucleophile and the solvent. The leaving group,
The attacking species
The loss of the leaving group,
Now, the weak nucleophile
The detailed, complete mechanism is as follows:
The outcome of the given reaction is predicted by considering factors like the nature of the leaving group, substrate, the strength of the reagent used, solvent, and temperature.
(f)
Interpretation:
The complete, detailed mechanism for the reaction is to be provided. The stereochemistry of the products is to be predicted where appropriate. If the reaction yields exclusively one product or a mixture of products, then the major product is to be determined.
Concept introduction:
For the prediction of the outcome of the

Answer to Problem 9.64P
The complete, detailed mechanism for the reaction is shown below:
Explanation of Solution
The given reaction is
The leaving group,
The attacking species
In the substrate, only one H atom can be eliminated. The leaving group and H atom are on same side.
The base deprotonates a hydrogen atom from the substrate and to yield the most substituted alkene as the product.
The detailed, complete mechanism is as follows:
The outcome of the given reaction is predicted by considering factors like the nature of the leaving group, substrate, the strength of the reagent used, solvent, and temperature.
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Chapter 9 Solutions
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