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Chapter 16: Problem 356

Predict the products of hydroboration-oxidation of: (a) cis-2-phenyl-2-butene; (b) trans \(-2\) -phenyl-2-butene; (c) 1 -methylcyclohexene.

Short Answer

Expert verified
The products of hydroboration-oxidation for the given compounds are: (a) 3-phenyl-2-butanol; (b) 3-phenyl-2-butanol; (c) 1-methylcyclohexanol.

Step by step solution

01

(a) Predicting the product of hydroboration-oxidation of cis-2-phenyl-2-butene

First, draw the structure of cis-2-phenyl-2-butene and identify the alkene group. Apply hydroboration followed by oxidation to this alkene. 1. Hydroboration: Add borane (BH3) to the alkene using anti-Markovnikov orientation and syn addition. The hydrogen atom adds to the least substituted carbon of the alkene, and the boron atom adds to the most substituted carbon. 2. Oxidation: Replace the boron atom with a hydroxyl group (OH) by treating the intermediate with hydrogen peroxide (H2O2) and a hydroxide ion (OH-). The final product of hydroboration-oxidation of cis-2-phenyl-2-butene is 3-phenyl-2-butanol.
02

(b) Predicting the product of hydroboration-oxidation of trans-2-phenyl-2-butene

Repeat the same process as in (a) but starting with trans-2-phenyl-2-butene. 1. Hydroboration: Add borane (BH3) to the alkene using anti-Markovnikov orientation and syn addition. 2. Oxidation: Replace the boron atom with a hydroxyl group (OH) using H2O2 and OH-. The final product of hydroboration-oxidation of trans-2-phenyl-2-butene is also 3-phenyl-2-butanol. This is because the stereochemistry of the starting alkene does not affect the product in this reaction, as the syn addition occurs on the same side of the alkene.
03

(c) Predicting the product of hydroboration-oxidation of 1-methylcyclohexene

Now, let's analyze 1-methylcyclohexene and follow the same procedure. 1. Hydroboration: Add borane (BH3) to the alkene using anti-Markovnikov orientation and syn addition. 2. Oxidation: Replace the boron atom with a hydroxyl group (OH) using H2O2 and OH-. The final product of hydroboration-oxidation of 1-methylcyclohexene is 1-methylcyclohexanol.

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Most popular questions from this chapter

Predict the products of each precursor by the hydration of olefins method. (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}_{2}\) Propylene Ethene

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The Infrared spectrum of cis-1,2-cyclopentanediol has an \(\mathrm{O}-\mathrm{H}\) stretching band at a lower frequency than for a free - OH group, and this band does not disappear even at high dilution. trans \(-1,2\) -Cyclopentanediol shows no such band. Can you suggest a possible explanation?

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