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1. BH3/THF 2. H₂O₂, OH-

1. BH3/THF 2. H₂O₂, OH-

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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Fill in the missing reagents or major products to complete the transformations. Be sure to pay careful
attention to stereochemistry where appropriate. If the major product is a pair of enantiomer you may
show one of them and indicate + enantiomer. If the products are diasteromers, show them both. 
 
 
**Organic Reaction: Hydroboration-Oxidation of Alkene** **Reaction Scheme:** The given reaction involves the conversion of an alkene (specifically, 3-methylcyclobutene) to an alcohol using the hydroboration-oxidation method. **Reactants and Reagents:** - **Reactant:** 3-methylcyclobutene (a four-membered ring with a double bond and a methyl group attached) - **Reagents:** 1. **BH₃/THF:** Borane in tetrahydrofuran (solvent) 2. **H₂O₂, OH⁻:** Hydrogen peroxide and a hydroxide ion (often from a base like NaOH) **Reaction Steps:** 1. **Hydroboration:** The first step involves the addition of borane (BH₃) to the double bond of the alkene in the presence of tetrahydrofuran (THF) to form a trialkylborane intermediate. 2. **Oxidation:** In the second step, hydrogen peroxide (H₂O₂) and a base (OH⁻) are used to oxidize the trialkylborane intermediate, replacing the boron atom with a hydroxyl group to form the final alcohol product. **Product:** - The product of this reaction is an alcohol derived from 3-methylcyclobutene, where the hydroxyl group (-OH) is added to the carbon that was originally part of the double bond, following anti-Markovnikov's rule (the -OH group attaches to the less substituted carbon in the double bond). **Mechanism Summary:** - The hydroboration step adds BH₃ across the double bond in a syn-addition manner (both hydrogen and boron are added to the same side of the double bond). - The oxidation step replaces the boron with a hydroxyl group, resulting in the formation of an alcohol. This reaction is a textbook example of hydroboration-oxidation, an important method in organic chemistry for converting alkenes to alcohols with a high degree of regioselectivity and stereoselectivity.
Transcribed Image Text:**Organic Reaction: Hydroboration-Oxidation of Alkene** **Reaction Scheme:** The given reaction involves the conversion of an alkene (specifically, 3-methylcyclobutene) to an alcohol using the hydroboration-oxidation method. **Reactants and Reagents:** - **Reactant:** 3-methylcyclobutene (a four-membered ring with a double bond and a methyl group attached) - **Reagents:** 1. **BH₃/THF:** Borane in tetrahydrofuran (solvent) 2. **H₂O₂, OH⁻:** Hydrogen peroxide and a hydroxide ion (often from a base like NaOH) **Reaction Steps:** 1. **Hydroboration:** The first step involves the addition of borane (BH₃) to the double bond of the alkene in the presence of tetrahydrofuran (THF) to form a trialkylborane intermediate. 2. **Oxidation:** In the second step, hydrogen peroxide (H₂O₂) and a base (OH⁻) are used to oxidize the trialkylborane intermediate, replacing the boron atom with a hydroxyl group to form the final alcohol product. **Product:** - The product of this reaction is an alcohol derived from 3-methylcyclobutene, where the hydroxyl group (-OH) is added to the carbon that was originally part of the double bond, following anti-Markovnikov's rule (the -OH group attaches to the less substituted carbon in the double bond). **Mechanism Summary:** - The hydroboration step adds BH₃ across the double bond in a syn-addition manner (both hydrogen and boron are added to the same side of the double bond). - The oxidation step replaces the boron with a hydroxyl group, resulting in the formation of an alcohol. This reaction is a textbook example of hydroboration-oxidation, an important method in organic chemistry for converting alkenes to alcohols with a high degree of regioselectivity and stereoselectivity.
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