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18. What are the major organic products of the following reaction? OH HO OH MnO2 A. LDA -78 °C Br

18. What are the major organic products of the following reaction? OH HO OH MnO2 A. LDA -78 °C Br

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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**18. What are the major organic products of the following reaction?** The chemical reaction depicted involves the transformation of an organic compound containing both a hydroxyl (OH) group and a bromine (Br) atom on a cyclohexane ring. 1. **Reaction Step 1:** - **Reagents: MnO₂** - Initial compound: Cyclohexyl alcohol with a bromine substituent. - Reaction A involves the oxidation of the alcohol group (OH) to a ketone using manganese dioxide (MnO₂). 2. **Reaction Step 2:** - **Reagents: LDA (Lithium Diisopropylamide), -78°C** - Intermediate product A is subjected to a strong, non-nucleophilic base, LDA, at low temperature (-78°C). This possibly induces deprotonation or a base-induced reaction forming a new intermediate, B. 3. **Reaction Step 3:** - **Reagents: Unknown diol** - The final reaction involves treatment of intermediate B with a diol. The hydroxyl groups (HO) suggest that a protective group or further functional transformation to form product C takes place. This sequence involves oxidation, base reaction at low temperature, and subsequent reaction with a diol to yield the major organic products of the reactions.
Transcribed Image Text:**18. What are the major organic products of the following reaction?** The chemical reaction depicted involves the transformation of an organic compound containing both a hydroxyl (OH) group and a bromine (Br) atom on a cyclohexane ring. 1. **Reaction Step 1:** - **Reagents: MnO₂** - Initial compound: Cyclohexyl alcohol with a bromine substituent. - Reaction A involves the oxidation of the alcohol group (OH) to a ketone using manganese dioxide (MnO₂). 2. **Reaction Step 2:** - **Reagents: LDA (Lithium Diisopropylamide), -78°C** - Intermediate product A is subjected to a strong, non-nucleophilic base, LDA, at low temperature (-78°C). This possibly induces deprotonation or a base-induced reaction forming a new intermediate, B. 3. **Reaction Step 3:** - **Reagents: Unknown diol** - The final reaction involves treatment of intermediate B with a diol. The hydroxyl groups (HO) suggest that a protective group or further functional transformation to form product C takes place. This sequence involves oxidation, base reaction at low temperature, and subsequent reaction with a diol to yield the major organic products of the reactions.
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