Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Alkanes and Cycloalkanes
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Give the major organic product(s) for the following reaction
### Chemical Reaction Sequence This image displays a chemical reaction sequence involving two main steps, designated to demonstrate the transformation of organic compounds. 1. **Starting Material (f):** - \( \text{CH}_3\text{C}\equiv\text{CH} \) - This is a propyne molecule, an alkyne with a triple bond between the second and third carbon atoms. 2. **Step 1: Base-Induced Deprotonation** - **Reagent:** \( \text{NaNH}_2 \) (sodium amide) - **Process:** The strong base sodium amide deprotonates the terminal alkyne to form an acetylide ion, resulting in intermediate \( \text{A} \). 3. **Step 2: Epoxide Addition** - **Intermediate A:** The acetylide ion reacts in this step. - **Reagent:** An epoxide with an oxygen atom in a three-membered ring - **Mechanism:** - The nucleophilic acetylide ion attacks the less hindered carbon in the epoxide ring, opening the ring. - The process is followed by the addition of water (\( \text{H}_2\text{O} \)) to stabilize and form the final product \( \text{B} \), which includes a hydroxyl group from the ring-opening reaction. ### Summary This sequence describes the conversion of propyne into a more complex alcohol derivative through the intermediary formation and subsequent reaction of an acetylide ion, a classic transformation in organic synthesis.
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Transcribed Image Text:### Chemical Reaction Sequence This image displays a chemical reaction sequence involving two main steps, designated to demonstrate the transformation of organic compounds. 1. **Starting Material (f):** - \( \text{CH}_3\text{C}\equiv\text{CH} \) - This is a propyne molecule, an alkyne with a triple bond between the second and third carbon atoms. 2. **Step 1: Base-Induced Deprotonation** - **Reagent:** \( \text{NaNH}_2 \) (sodium amide) - **Process:** The strong base sodium amide deprotonates the terminal alkyne to form an acetylide ion, resulting in intermediate \( \text{A} \). 3. **Step 2: Epoxide Addition** - **Intermediate A:** The acetylide ion reacts in this step. - **Reagent:** An epoxide with an oxygen atom in a three-membered ring - **Mechanism:** - The nucleophilic acetylide ion attacks the less hindered carbon in the epoxide ring, opening the ring. - The process is followed by the addition of water (\( \text{H}_2\text{O} \)) to stabilize and form the final product \( \text{B} \), which includes a hydroxyl group from the ring-opening reaction. ### Summary This sequence describes the conversion of propyne into a more complex alcohol derivative through the intermediary formation and subsequent reaction of an acetylide ion, a classic transformation in organic synthesis.
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