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Chapter 6: Problem 18

Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) S-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanol

Short Answer

Expert verified
Answer: The alkenes that will produce the specified alcohols upon acid-catalyzed hydration are (a) 2-Hexene, (b) 1-Methylcyclobutene, (c) 2-Methyl-1-Butene, and (d) 1-Propene.

Step by step solution

01

Identify the alcohol structure

S-Hexanol has a hydroxyl group (-OH) on the third carbon atom in a straight-chain hexane molecule. Structure: CH3-CH2-CH(OH)-CH2-CH2-CH3
02

Determine the alkene that will produce S-Hexanol upon acid-catalyzed hydration

We need to find an alkene that will follow Markovnikov's rule and produce the observed alcohol when an -OH group is added. The alkene which will produce S-Hexanol upon hydration is: Alkene: CH3-CH2-CH=CH-CH2-CH3 (2-Hexene) (b) 1-Methylcyclobutanol:
03

Identify the alcohol structure

1-Methylcyclobutanol has a hydroxyl group (-OH) on the first carbon atom and a methyl group (CH3) on the second carbon atom in a cyclobutane ring. Structure: CH3 | C / \ C - OH / \ C C
04

Determine the alkene that will produce 1-Methylcyclobutanol upon acid-catalyzed hydration

The alkene which will produce 1-Methylcyclobutanol upon hydration is: Alkene: CH3 | C / \ C = C / \ C C (c) 2-Methyl-2-butanol:
05

Identify the alcohol structure

2-Methyl-2-butanol has a hydroxyl group (-OH) on the second carbon atom and a methyl group (CH3) on the same carbon atom in a straight-chain butane molecule. Structure: CH3-C(CH3)(OH)-CH2-CH3
06

Determine the alkene that will produce 2-Methyl-2-butanol upon acid-catalyzed hydration

The alkene which will produce 2-Methyl-2-butanol upon hydration is: Alkene: CH3-C(CH3)=CH-CH3 (2-Methyl-1-Butene) (d) 2-Propanol:
07

Identify the alcohol structure

2-Propanol has a hydroxyl group (-OH) on the second carbon atom in a straight-chain propane molecule. Structure: CH3-CH(OH)-CH3
08

Determine the alkene that will produce 2-Propanol upon acid-catalyzed hydration

The alkene which will produce 2-Propanol upon hydration is: Alkene: CH3-CH=CH2 (1-Propene)

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Most popular questions from this chapter

The heat of hydrogenation of cis-2,2,5,5-tetramethyl-3-hexene is \(-154 \mathrm{~kJ}\) (-36.7 kcal)/ \(\mathrm{mol}\), while that of the trans isomer is only \(-119 \mathrm{~kJ}\) (-26.9 kcal) \(/ \mathrm{mol}\). (a) Why is the heat of hydrogenation of the cis isomer so much larger (more negative) than that of the trans isomer? (b) If a catalyst could be found that allowed equilibration of the cis and trans isomers at room temperature (such catalysts do exist), what would be the ratio of trans to is isomers?

Draw the alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free energy differences between equatorial and axial substituents on a cyclohexane ring are \(21 \mathrm{~kJ}\) ( \(4.9 \mathrm{kcal}) / \mathrm{mol}\) for tert-butyl and \(2.0-2.6 \mathrm{~kJ}(0.48-0.62 \mathrm{kcal}) / \mathrm{mol}\) for bromine. Estimate the relative percentages of the alternative chair conformations you drew in the first part of this problem.

Predict the organic product(s) of the reaction of 2-butene with each reagent. (a) \(\mathrm{H}_{2} \mathrm{O}\left(\mathrm{H}_{2} \mathrm{SO}_{4}\right)\) (b) \(\mathrm{Br}_{2}\) (c) \(\mathrm{Cl}_{2}\) (d) \(\mathrm{Br}_{2}\) in \(\mathrm{H}_{2} \mathrm{O}\) (e) \(\mathrm{HI}\) (f) \(\mathrm{Cl}_{2}\) in \(\mathrm{H}_{2} \mathrm{O}\) (g) \(\operatorname{Hg}(\mathrm{OAc})_{2}, \mathrm{H}_{2} \mathrm{O}\) (h) product (g) \(+\mathrm{NaBH}_{4}\)

When 2-pentene is treated with \(\mathrm{Cl}_{2}\) in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).

The acid-catalyzed hydration of 3,3-dimethyl-1-butene gives 2,3 -dimethyl-2-butanol as the major product. Propose a mechanism for the formation of this alcohol.
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