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2-Methyl-but-1-ene plus 1) BH3•THF; 2) H2O2, OH" yie 2-methylbutane 2-methyl-butan-3-one

2-Methyl-but-1-ene plus 1) BH3•THF; 2) H2O2, OH" yie 2-methylbutane 2-methyl-butan-3-one

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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### Question: **2-Methyl-but-1-ene plus 1) BH₃⋅THF; 2) H₂O₂, OH⁻ yields what product?** ### Options: - ☐ 2-methylbutane - ☐ 2-methyl-butan-3-one - ☐ 3-methyl-butanoic acid - ☐ 2-methyl-butan-2-ol - ☐ 2-methyl-butan-1-ol ### Explanation: This question is based on the hydroboration-oxidation reaction mechanism, which is a two-step process commonly used to convert alkenes to alcohols. The first step involves the addition of borane (BH₃) in tetrahydrofuran (THF) to the alkene, and the second step involves oxidation using hydrogen peroxide (H₂O₂) in the presence of a hydroxide ion (OH⁻). #### Step-by-Step Reaction Mechanism: 1. **Hydroboration:** The BH₃ adds across the double bond of 2-methyl-but-1-ene. The boron atom attaches to the less substituted carbon (anti-Markovnikov addition). 2. **Oxidation:** The boron is then replaced by an OH group from the H₂O₂/NaOH, resulting in the formation of an alcohol. ### Correct Answer: The product of the reaction between 2-methyl-but-1-ene, BH₃⋅THF, H₂O₂, and OH⁻ is **2-methyl-butan-1-ol**. - ☐ 2-methylbutane - ☐ 2-methyl-butan-3-one - ☐ 3-methyl-butanoic acid - ☐ 2-methyl-butan-2-ol - ☑ **2-methyl-butan-1-ol** This product is formed due to the anti-Markovnikov addition of BH₃ and subsequent oxidation, resulting in the alcohol group attaching to the less substituted carbon atom of the original alkene.
Transcribed Image Text:### Question: **2-Methyl-but-1-ene plus 1) BH₃⋅THF; 2) H₂O₂, OH⁻ yields what product?** ### Options: - ☐ 2-methylbutane - ☐ 2-methyl-butan-3-one - ☐ 3-methyl-butanoic acid - ☐ 2-methyl-butan-2-ol - ☐ 2-methyl-butan-1-ol ### Explanation: This question is based on the hydroboration-oxidation reaction mechanism, which is a two-step process commonly used to convert alkenes to alcohols. The first step involves the addition of borane (BH₃) in tetrahydrofuran (THF) to the alkene, and the second step involves oxidation using hydrogen peroxide (H₂O₂) in the presence of a hydroxide ion (OH⁻). #### Step-by-Step Reaction Mechanism: 1. **Hydroboration:** The BH₃ adds across the double bond of 2-methyl-but-1-ene. The boron atom attaches to the less substituted carbon (anti-Markovnikov addition). 2. **Oxidation:** The boron is then replaced by an OH group from the H₂O₂/NaOH, resulting in the formation of an alcohol. ### Correct Answer: The product of the reaction between 2-methyl-but-1-ene, BH₃⋅THF, H₂O₂, and OH⁻ is **2-methyl-butan-1-ol**. - ☐ 2-methylbutane - ☐ 2-methyl-butan-3-one - ☐ 3-methyl-butanoic acid - ☐ 2-methyl-butan-2-ol - ☑ **2-methyl-butan-1-ol** This product is formed due to the anti-Markovnikov addition of BH₃ and subsequent oxidation, resulting in the alcohol group attaching to the less substituted carbon atom of the original alkene.
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