Concept explainers
17-73 Alcohols can be prepared by the acid-catalyzed hydration of
(a) Ethanol
(b) Cyclohexanol
(c) 2-Propanol
(d) 1-Phenylethanol
(a)
Interpretation:
Show the preparation of ethanol by acid-catalyzed hydration of an alkene and by reduction of an aldehyde or a ketone.
Concept Introduction:
Acid-catalyzed hydration of alkenes: In the presence of an acid catalyst
Reduction of an aldehyde or a ketone: The C=C double bond of an alkene is reduced by hydrogen in the presence of a transition metal catalyst to a C−C single bond. The same is true for the C=O double bond of an aldehyde or a ketone. Aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohol.
Answer to Problem 17.73P
By acid-catalyzed hydration of ethane:
By Reduction of ethanal:
Explanation of Solution
By acid-catalyzed hydration of ethane:
When ethene is allowed to react with water in presence of an acid catalyst it gives ethanol.
By Reduction of ethanal: When ethanal is reduced in the presence of sodium borohydride it gives ethanol.
(b)
Interpretation:
Show the preparation of cyclohexanol by acid-catalyzed hydration of an alkene and by reduction of an aldehyde or a ketone.
Concept Introduction:
Acid-catalyzed hydration of alkenes: In the presence of an acid catalyst
Reduction of an aldehyde or a ketone: The C=C double bond of an alkene is reduced by hydrogen in the presence of a transition metal catalyst to a C−C single bond. The same is true for the C=O double bond of an aldehyde or a ketone. Aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohol.
Answer to Problem 17.73P
By acid-catalyzed hydration of ethane:
By Reduction of ethanal:
Explanation of Solution
By acid-catalyzed hydration of ethane: When cyclohexene is allowed to react with water in presence of an acid catalyst it gives cyclohexanol.
By Reduction of ethanal: When cyclohexanone is reduced in the presence of sodium borohydride it gives cyclohexanol.
(c)
Interpretation:
Show the preparation of 2-propanol by acid-catalyzed hydration of an alkene and by reduction of an aldehyde or a ketone.
Concept Introduction:
Acid-catalyzed hydration of alkenes: In the presence of an acid catalyst
Reduction of an aldehyde or a ketone: The C=C double bond of an alkene is reduced by hydrogen in the presence of a transition metal catalyst to a C−C single bond. The same is true for the C=O double bond of an aldehyde or a ketone. Aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohol.
Answer to Problem 17.73P
By acid-catalyzed hydration of ethane:
By Reduction of ethanal:
Explanation of Solution
By acid-catalyzed hydration of ethane: When propene is allowed to react with water in presence of an acid catalyst it gives 2-propanol.
By Reduction of ethanal: When acetone is reduced in the presence of sodium borohydride it gives 2-propanol.
(d)
Interpretation:
Show the preparation of 1-phenylethanol by acid-catalyzed hydration of an alkene and by reduction of an aldehyde or a ketone.
Concept Introduction:
Acid-catalyzed hydration of alkenes: In the presence of an acid catalyst
Reduction of an aldehyde or a ketone: The C=C double bond of an alkene is reduced by hydrogen in the presence of a transition metal catalyst to a C−C single bond. The same is true for the C=O double bond of an aldehyde or a ketone. Aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohol.
Answer to Problem 17.73P
By acid-catalyzed hydration of ethane:
By Reduction of ethanal:
Explanation of Solution
By acid-catalyzed hydration of ethane: When 1-phenylethene is allowed to react with water in presence of an acid catalyst it gives 1-phenylethanol.
By Reduction of ethanal: When acetophenone is reduced in the presence of sodium borohydride it gives 1-phenylethanol.
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Chapter 17 Solutions
Introduction to General, Organic and Biochemistry
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- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning