Concept explainers
Interpretation:
The structural formulas of five other
Concept Introduction:
The acid catalyzed hydration of alkenes result in the formation of alcohols. In this reaction, the hydrogen ion from the acid reacts with the pi electrons of the double bond resulting formation of carbocation. This carbocation can reacts with the lone pair on oxygen atom resulting substitution of hydronium ion group on the carbon having positive charge. The
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OWLv2 for Bettelheim/Brown/Campbell/Farrell/Torres' Introduction to General, Organic and Biochemistry, 11th Edition, [Instant Access], 1 term (6 months)
- Draw the structural formula of an alkene that undergoes acid-catalyzed hydration to give each of the following alcohols as the major product. More than one alkene may give each compound as the major productarrow_forward12-50 Draw the structural formula of an alkene that undergoes acid-catalyzed hydration to give the indicated alcohol as the major product. More than one alkene may give each alcohol as the major product. 3-Hexanol 1-Methylcyclobutanol 2-Methyl-2-butanol 2-Propanolarrow_forward14-78 Consider alkenes A, B, and C. each of which has the same molecular formula, C(.H12. Alkenes B and C can each be separated into cis and trans isomers. Upon catalytic reduction using H,, in the presence of a transition metal catalyst (Ni, Pd, or Pt>, alkenes A, B, and C all give hexane as the only product. Acid- catalyzed hydration of alkene C gives one alcohol with the molecular formula CeH14O. Acid catalyzed- hydration of alkene B gives an equal mixture of two alcohols, each with the molecular formula C6H14O. Acid-catalyzed hydration of alkene C gives only a single alcohol with the molecular formula C6H14O. Propose structural formulas for alkenes A, B, and C and the alcohols formed by acid-catalyzed hydration of each, consistent with these experimental results.arrow_forward
- 13-20 Three products with the molecular formula CgH^BrCl form when bromobenzene is treated with chlorine, Cl2, in the presence of FeCl3 as a catalyst. Name and draw a structural formula for each product.arrow_forward17-73 Alcohols can be prepared by the acid-catalyzed hydration of alkenes (Section 12-6B) and by the reduction of aldehydes and ketones (Section 17-4B). Show how you might prepare each of the following alcohols by (1) acid-catalyzed hydration of an alkene and (2) reduction of an aldehyde or a ketone. (a) Ethanol (b) Cyclohexanol (c) 2-Propanol (d) 1-Phenylethanolarrow_forward14-28 Give the structural formula of an alkene or alkenes from which each alcohol can be prepared. 2-Butanol 1-Methylcyclohexanol 3-Hexanol 2-Methyl-2-pentanol Cyclopentanolarrow_forward
- 13-19 Suppose you have unlabeled bottles of benzene and cyclohexene. What chemical reaction could you use to tell which bottle contains which chemical? Explain what you would do, what you would expect to see, and how you would explain your observations. Write an equation for a positive test.arrow_forward14-49 Answer true or false. Today, the major carbon sources for the synthesis of methanol are coal and methane (natural gas), both nonrenewable resources. Today the major carbon sources for the synthesis of ethanol are petroleum and natural gas, both nonrenewable resources. Intermolecular acid-catalyzed dehydration of ethanol gives diethyl ether. Conversion of ethylene to ethylene glycol involves oxidation to ethylene oxide, followed by acid-catalyzed hydration (addition of water, to ethylene oxide. Ethylene glycol is soluble in water in all proportions. A major use of ethylene glycol is as automobile antifreeze.arrow_forwardFollowing is the structural formula of hexabromocyclododecane. This compound was at one time used as a flame retardant in polystyrene foam insulation in buildings, but has now been banned because it had been shown to be toxic to aquatic organisms, and can disrupt thyroid hormone levels in laboratory test animals. In addition, it persists in the environment. Show how this flame retardant could be synthesized from a cycloalkatriene and write the structural formula and IUPAC name of this starting material. Br Hexabromocyclododecanearrow_forward
- 14-33 Write equations for the reaction of 1-butanol, a primary alcohol, with these reagents. H2SO4, heat K2Cr2O7, H2SO4arrow_forwardPropose an explanation for the following experimental observations: Acid-catalyzed hydration of 1-hexene gives a single alcohol in high yield. Acid-catalyzed hydration of cis- or f rans-2-hexene gives a mixture of two alcohols in approximately equal amounts. Acid-catalyzed hydration of cis- or irnns-3-hexene gives a single alcohol in high yield.arrow_forward13-15 Draw structural formulas for these compounds l-Bromo-2-chloro-4-ethylbenzene 4-Bromo-l,2-dimethylbenzene 2,4,6-Trinitrotoluene 4-Phenyl-l-pentene p-Cresol (D 2,4-Dichlorophenolarrow_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