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 67P
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 67P
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 67P
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 67P
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 16 Solutions
Introduction To General, Organic, And Biochemistry
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- In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H100) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCI) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answerarrow_forwardAlcohol A (C10H18O) is converted to a mixture of alkenes B and C on being heated with potassium hydrogen sulfate (KHSO4). Catalytic hydrogenation of B and C yields the same product. Assuming that dehydration of alcohol A proceeds without rearrangement, deduce the structures of alcohol A and alkene C.arrow_forwardDraw a structural formula for an alkene with the indicated molecular formula that gives the compound shown as the major product (more than one alkene may give the same compound as the major product).arrow_forward
- 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