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CH3 CH3 H BH2 BH2 H3C H2 CH2 H3C

CH3 CH3 H BH2 BH2 H3C H2 CH2 H3C

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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### Alkenes Hydration via Borane Addition **Chemical Reaction:** 1. Reactant: - Alkene: CH₃CH=CHCH₂CH₃ 2. Reagents: - 1. BH₃, THF - 2. NaOH, H₂O, H₂O₂ 3. Product: - Alcohol: CH₃CH₂CH₂CH₂CH₂OH **Explanation:** Alkenes can be hydrated via the addition of borane (BH₃) to yield alcohols with non-Markovnikov regiochemistry. The boron atom acts as an electrophile and typically follows Markovnikov's rule by adding to the carbon with the most hydrogens. Upon oxidation of the alkylborane using basic peroxide, the product obtained is an alcohol. **Mechanism Step:** The instruction involves drawing curved arrows to show the movement of electrons in this step of the mechanism: 1. **Arrow-Pushing Instructions:** - Two curved arrows are shown indicating electron movement between molecules such as the lone pairs and bonds. 2. **Diagram Explanation:** - **Left Side:** - Structure involves OR groups bonded to Boron (B) and a hydroxide ion (OH⁻). - **Right Side:** - The OR groups remain bonded to the boron, now also bonded to OH. Use these visualizations to understand how electrons are transferred in this mechanistic step, leading to the formation of the alcohol product. **Interactive Elements:** - "Submit Answer": To input your solution. - "Retry Entire Group": To retry the exercise. - "9 more group attempts remaining": Counts remaining attempts for practicing the mechanism. --- Ensure to illustrate the movement of electrons accurately, practicing the drawing of arrows for better comprehension.
Transcribed Image Text:### Alkenes Hydration via Borane Addition **Chemical Reaction:** 1. Reactant: - Alkene: CH₃CH=CHCH₂CH₃ 2. Reagents: - 1. BH₃, THF - 2. NaOH, H₂O, H₂O₂ 3. Product: - Alcohol: CH₃CH₂CH₂CH₂CH₂OH **Explanation:** Alkenes can be hydrated via the addition of borane (BH₃) to yield alcohols with non-Markovnikov regiochemistry. The boron atom acts as an electrophile and typically follows Markovnikov's rule by adding to the carbon with the most hydrogens. Upon oxidation of the alkylborane using basic peroxide, the product obtained is an alcohol. **Mechanism Step:** The instruction involves drawing curved arrows to show the movement of electrons in this step of the mechanism: 1. **Arrow-Pushing Instructions:** - Two curved arrows are shown indicating electron movement between molecules such as the lone pairs and bonds. 2. **Diagram Explanation:** - **Left Side:** - Structure involves OR groups bonded to Boron (B) and a hydroxide ion (OH⁻). - **Right Side:** - The OR groups remain bonded to the boron, now also bonded to OH. Use these visualizations to understand how electrons are transferred in this mechanistic step, leading to the formation of the alcohol product. **Interactive Elements:** - "Submit Answer": To input your solution. - "Retry Entire Group": To retry the exercise. - "9 more group attempts remaining": Counts remaining attempts for practicing the mechanism. --- Ensure to illustrate the movement of electrons accurately, practicing the drawing of arrows for better comprehension.
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. **Mechanism Explanation:** 1. **Reagents:** - Step 1: BH₃, THF - Step 2: NaOH, H₂O, H₂O₂ 2. **Reaction Steps:** - Initial compound: 4-methylpent-1-ene. - Borane (BH₃) adds to the alkene, followed by the oxidation step, resulting in an alcohol. 3. **Diagrams:** - The starting alkene is shown on the left, reacting with borane to form an intermediate where BH₂ is attached to the less substituted carbon. - Oxidation results in the conversion of the BH₂ group to an OH group, yielding the final alcohol product on the right. **Instruction:** - Draw curved arrows to show the movement of electrons in this step of the mechanism. **Arrow-pushing Instructions:** - Illustrates typical electron movement with arrows. - A depiction of the transition from alkene to alkylborane is shown, highlighting where to apply the electron-pushing technique. Interactive options: - Buttons for submitting or retrying answers are shown below the reaction diagram.
Transcribed Image Text:Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. **Mechanism Explanation:** 1. **Reagents:** - Step 1: BH₃, THF - Step 2: NaOH, H₂O, H₂O₂ 2. **Reaction Steps:** - Initial compound: 4-methylpent-1-ene. - Borane (BH₃) adds to the alkene, followed by the oxidation step, resulting in an alcohol. 3. **Diagrams:** - The starting alkene is shown on the left, reacting with borane to form an intermediate where BH₂ is attached to the less substituted carbon. - Oxidation results in the conversion of the BH₂ group to an OH group, yielding the final alcohol product on the right. **Instruction:** - Draw curved arrows to show the movement of electrons in this step of the mechanism. **Arrow-pushing Instructions:** - Illustrates typical electron movement with arrows. - A depiction of the transition from alkene to alkylborane is shown, highlighting where to apply the electron-pushing technique. Interactive options: - Buttons for submitting or retrying answers are shown below the reaction diagram.
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