3 **Reaction Selectivity and Observed Products in Organic Chemistry****Question:**When subjected to the reaction conditions below, the diol product was observed, but the expected intramolecular epoxide product was not isolated. Using drawings and a word explanation, explain this observed selectivity.**Reaction Conditions and Observations:**The starting material is a bromine-containing cyclic alcohol. When this compound is treated with sodium hydroxide (NaOH) in tetrahydrofuran (THF), the expected reaction involves nucleophilic substitution and potential cyclization to form an epoxide. However, instead of the epoxide, a diol product is observed.**Reaction Details:**1. **Reagents and Solvents:** - **NaOH**: A strong base used in the reaction. - **THF (Tetrahydrofuran)**: An aprotic solvent.2. **Structures:** - Starting material: A cyclohexanol derivative with a bromine substituent. - Products: - Observed major product: A diol with hydroxyl groups at adjacent positions. - Observed minor product: An epoxide that was not isolated.**Explanation of Selectivity:**The reaction involves base-promoted deprotonation and substitution processes. The observed selectivity for the diol formation over the expected epoxide is likely due to the steric and electronic interactions in the reaction intermediate. The formation of the diol suggests that intermolecular reactions favored over the competitive intramolecular cyclization to form the epoxide. This can be due to: - **Stability and Accessibility:** The hydroxide ion's approach and reaction site availability may favor the diol pathway. - **Steric Hindrance and Ring Strain:** The formation of a three-membered epoxide ring can introduce significant strain, which makes the intramolecular path less favorable.- **Kinetics and Reaction Pathway:** The kinetic accessibility of forming the diol might be favored under the given conditions.This reaction emphasizes the importance of considering steric and electronic effects, solvent choice, and reaction conditions when predicting and executing organic synthesis.

Answered: Image /qna-images/answer/08d4fdf9-de5b-4470-a1ad-291b582369a0.jpg

3. When subjected to reaction conditions below, the diol product was observed, but the expected intramolecular epoxide product was not isolated. Using drawings and a word explanation, explain this observed selectivity. OH OH NaOH Me. "Br Me Me THE OH Me Me Me . le Me Me obse rved produt

3. When subjected to reaction conditions below, the diol product was observed, but the expected intramolecular epoxide product was not isolated. Using drawings and a word explanation, explain this observed selectivity. OH OH NaOH Me. "Br Me Me THE OH Me Me Me . le Me Me obse rved produt

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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