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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Provide the major organic product(s) for the reaction shown below
Transcribed Image Text:### Hydroboration-Oxidation and Grignard Reaction
#### Reaction Scheme Breakdown
**Starting Material:**
The starting material is an alkene with a terminal alkyne group.
**Step 1: Hydroboration-Oxidation**
1. **Reagents:**
- BH₃/THF
- H₂O₂, OH⁻, H₂O
**Process:**
This step involves the hydroboration-oxidation of the alkyne. BH₃ (Borane) in THF (Tetrahydrofuran) adds to the alkyne, followed by oxidation with hydrogen peroxide (H₂O₂) in a basic medium (OH⁻), which leads to the formation of an intermediate compound 'A'.
**Step 2: Grignard Reaction**
1. **Reagents:**
- CH₃MgBr (Methylmagnesium bromide)
- H₂O or H₃O⁺
**Process:**
This involves the treatment of the intermediate 'A' with the Grignard reagent (CH₃MgBr), followed by hydrolysis using water or an acidic medium like H₃O⁺, resulting in the final product 'B'.
**Expected Products:**
Two main products (A and B) are to be identified from these reactions. Each product corresponds to the transformation sequences carried out in the steps mentioned above.
#### Detailed Explanation:
1. **Hydroboration-Oxidation:**
- **Mechanism:**
- BH₃ adds to the triple bond of the terminal alkyne, creating a trialkylborane intermediate.
- This intermediate is then oxidized by H₂O₂ in the presence of a base (OH⁻) converting it to an alcohol.
2. **Grignard Reaction:**
- **Mechanism:**
- The intermediate alcohol obtained from the hydroboration-oxidation undergoes nucleophilic addition with the Grignard reagent (CH₃MgBr).
- This step results in the formation of a secondary alcohol through a nucleophilic attack followed by protonation during hydrolysis.
#### Key Points:
- **First Product (A):** An intermediate alcohol produced from hydroboration-oxidation.
- **Second Product (B):** The final alcohol created through the Grignard reaction.
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