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Draw the product of the following sequence of reactions. Show stereochemistry.

Draw the product of the following sequence of reactions. Show stereochemistry.

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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Draw the product of the following sequence of reactions. Show stereochemistry.

**Transcription and Explanation for Educational Purposes** **Chemical Reaction Diagram:** The image depicts a chemical reaction sequence involving a stereochemical transformation of an alcohol group. 1. **Starting Material:** - The structure displayed at the top left of the image is a molecular structure representing a chiral alcohol. It is an alcohol group (OH) attached to a carbon, indicated by the wedge, signifying specific stereochemistry. 2. **Reaction Conditions:** - **Step 1:** - Reagents: TsCl (p-toluenesulfonyl chloride), pyr (pyridine) - The role of TsCl (p-toluenesulfonyl chloride) is to convert the alcohol into a tosylate, which is a good leaving group. - Pyridine is used as a base to facilitate the reaction by accepting the hydrogen from the alcohol group. - **Step 2:** - Reagents: NaN₃ (sodium azide), DMF (dimethylformamide) - This step involves the substitution of the tosylate with the azide ion (N₃⁻), resulting in an inversion of stereochemistry, a common feature of SN2 reactions. - DMF is used as a solvent for this reaction, as it can dissolve many salts and is polar aprotic, which is suitable for SN2 mechanisms. 3. **Overall Reaction:** - The given diagram represents a two-step transformation of an alcohol into an azide via a tosylate intermediate, using the aforementioned reagents. The stereochemical outcome is an inversion due to the SN2 reaction in the second step.
Transcribed Image Text:**Transcription and Explanation for Educational Purposes** **Chemical Reaction Diagram:** The image depicts a chemical reaction sequence involving a stereochemical transformation of an alcohol group. 1. **Starting Material:** - The structure displayed at the top left of the image is a molecular structure representing a chiral alcohol. It is an alcohol group (OH) attached to a carbon, indicated by the wedge, signifying specific stereochemistry. 2. **Reaction Conditions:** - **Step 1:** - Reagents: TsCl (p-toluenesulfonyl chloride), pyr (pyridine) - The role of TsCl (p-toluenesulfonyl chloride) is to convert the alcohol into a tosylate, which is a good leaving group. - Pyridine is used as a base to facilitate the reaction by accepting the hydrogen from the alcohol group. - **Step 2:** - Reagents: NaN₃ (sodium azide), DMF (dimethylformamide) - This step involves the substitution of the tosylate with the azide ion (N₃⁻), resulting in an inversion of stereochemistry, a common feature of SN2 reactions. - DMF is used as a solvent for this reaction, as it can dissolve many salts and is polar aprotic, which is suitable for SN2 mechanisms. 3. **Overall Reaction:** - The given diagram represents a two-step transformation of an alcohol into an azide via a tosylate intermediate, using the aforementioned reagents. The stereochemical outcome is an inversion due to the SN2 reaction in the second step.
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