Textbook Question
Predict the major products of the following reactions. Include stereochemistry where applicable.
(b) trans-4,4-dimethylpent-2-ene + BH3⋅THF then H2O2, OH–
10. Addition Reactions
Hydroboration
6:23 minutesProblem 10a,b
Textbook Question
Predict the major products of the following reactions.
a. propene + BH3⋅THF
b. the product from part (a) + H2O2/OH−
Verified step by step guidance1
Step 1: Understand the reaction in part (a). Propene reacts with BH3 in the presence of THF (tetrahydrofuran) in a hydroboration reaction. This reaction follows anti-Markovnikov addition, where the boron atom attaches to the less substituted carbon of the double bond in propene.
Step 2: Recognize the stereochemistry of the hydroboration reaction. The addition of BH3 occurs in a syn fashion, meaning both the boron and hydrogen add to the same side of the double bond.
Step 3: Analyze the product of part (a). The product will be an organoborane intermediate, where the boron atom is bonded to the less substituted carbon of the original double bond in propene.
Step 4: Understand the reaction in part (b). The organoborane intermediate from part (a) reacts with H2O2 and OH− in an oxidation reaction. This converts the boron atom into a hydroxyl group (-OH), resulting in an alcohol.
Step 5: Predict the major product of part (b). The hydroxyl group will attach to the less substituted carbon of the original double bond in propene, following anti-Markovnikov addition. The stereochemistry of the product will retain the syn addition from part (a).
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Video duration:
6mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydroboration-Oxidation
Hydroboration-oxidation is a two-step reaction process used to convert alkenes into alcohols. In the first step, an alkene reacts with borane (BH3) in tetrahydrofuran (THF) to form an organoborane intermediate. This step is characterized by syn-addition, leading to the formation of a trialkylborane. The second step involves oxidation with hydrogen peroxide (H2O2) and hydroxide ions (OH−), resulting in the formation of an alcohol.
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General properties of hydroboration-oxidation.
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the hydroboration step, the boron atom adds to the less substituted carbon of the alkene, following Markovnikov's rule. This results in the formation of a more stable, primary alcohol after oxidation, demonstrating the regioselective nature of the reaction.
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Stereochemistry
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the hydroboration-oxidation process, the addition of boron and subsequent oxidation occurs in a syn fashion, meaning that both the boron and the hydroxyl group will end up on the same side of the molecule. This stereochemical outcome is important for predicting the configuration of the final alcohol product.
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