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Determine the major product of the following reaction: BH3 OH, H2O2

Determine the major product of the following reaction: BH3 OH, H2O2

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Determine the major product of the following reaction:** The reaction starts with 3-methyl-1-butene, a molecule with a double bond between the first and second carbon atoms and a methyl group (-CH3) attached to the third carbon atom. The reactant undergoes hydroboration-oxidation, a two-step reaction involving BH3 (borane) followed by OH- (hydroxide) and H2O2 (hydrogen peroxide). **Step-by-Step Explanation of the Reaction:** 1. **Hydroboration:** - BH3 adds across the double bond in a syn-addition manner, meaning the boron atom attaches to the less substituted carbon (the carbon with more hydrogen atoms), and the hydrogen atom attaches to the more substituted carbon (the carbon with fewer hydrogen atoms). - For 3-methyl-1-butene, BH3 adds to the carbons in a way that the boron atom attaches to the terminal carbon (C1), and the hydrogen atom attaches to the second carbon (C2). 2. **Oxidation:** - In this step, the boron atom is replaced by a hydroxyl group (-OH). - The hydrogen peroxide (H2O2) in the presence of hydroxide ions (OH-) facilitates this substitution. - This conversion produces an alcohol. **Major Product Formation:** Given that the boron in BH3 initially attaches to the less substituted carbon (C1), the final product after oxidation is 3-methyl-1-butanol. Thus, the major product of the hydroboration-oxidation reaction of 3-methyl-1-butene is 3-methyl-1-butanol.
Transcribed Image Text:**Determine the major product of the following reaction:** The reaction starts with 3-methyl-1-butene, a molecule with a double bond between the first and second carbon atoms and a methyl group (-CH3) attached to the third carbon atom. The reactant undergoes hydroboration-oxidation, a two-step reaction involving BH3 (borane) followed by OH- (hydroxide) and H2O2 (hydrogen peroxide). **Step-by-Step Explanation of the Reaction:** 1. **Hydroboration:** - BH3 adds across the double bond in a syn-addition manner, meaning the boron atom attaches to the less substituted carbon (the carbon with more hydrogen atoms), and the hydrogen atom attaches to the more substituted carbon (the carbon with fewer hydrogen atoms). - For 3-methyl-1-butene, BH3 adds to the carbons in a way that the boron atom attaches to the terminal carbon (C1), and the hydrogen atom attaches to the second carbon (C2). 2. **Oxidation:** - In this step, the boron atom is replaced by a hydroxyl group (-OH). - The hydrogen peroxide (H2O2) in the presence of hydroxide ions (OH-) facilitates this substitution. - This conversion produces an alcohol. **Major Product Formation:** Given that the boron in BH3 initially attaches to the less substituted carbon (C1), the final product after oxidation is 3-methyl-1-butanol. Thus, the major product of the hydroboration-oxidation reaction of 3-methyl-1-butene is 3-methyl-1-butanol.
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