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Explain why the following reactions do not work Br OMS Br NaOH / H₂O Heat NaOH Acetone NaOH / H₂O Heat

Explain why the following reactions do not work Br OMS Br NaOH / H₂O Heat NaOH Acetone NaOH / H₂O Heat

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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**Title: Understanding Why Certain Reactions Do Not Work** In this section, we will explore why some chemical reactions fail to proceed as expected. We'll examine three different reactions, each involving different conditions and reactants. --- **Reaction 1:** - **Reactants:** A cyclohexane ring with a bromine (Br) substituent. - **Reagents/Conditions:** Sodium hydroxide (NaOH) in water (H₂O) with heat. - **Expected Product:** A cyclohexene ring (an alkene). In this reaction, the bromine is expected to be eliminated to form a double bond (alkene). However, under these conditions, the reaction does not proceed. This could be due to the stability of the starting material or unfavorable reaction conditions. --- **Reaction 2:** - **Reactants:** A linear alkane with a methanesulfonate (OMs) substituent. - **Reagents/Conditions:** Sodium hydroxide (NaOH) in acetone. - **Expected Product:** A linear alkene. Here, the methanesulfonate group is expected to leave, allowing the formation of a double bond. The reaction is likely hindered by the solvent choice or the stability of the leaving group. --- **Reaction 3:** - **Reactants:** A cyclohexane ring with a bromine (Br) and an ethyl group. - **Reagents/Conditions:** Sodium hydroxide (NaOH) in water (H₂O) with heat. - **Expected Product:** A cyclohexene ring with an ethyl group (an alkene). Similar to the first reaction, the presence of heat and a strong base typically facilitates elimination. However, this reaction does not occur as expected, possibly due to steric hindrance or poor leaving group ability. --- **Conclusion:** These examples highlight the complexities of chemical reactions, where factors such as the type of solvent, temperature, and nature of the leaving group can dramatically influence the outcome. Understanding these intricacies is crucial for successful reaction planning and execution.
Transcribed Image Text:**Title: Understanding Why Certain Reactions Do Not Work** In this section, we will explore why some chemical reactions fail to proceed as expected. We'll examine three different reactions, each involving different conditions and reactants. --- **Reaction 1:** - **Reactants:** A cyclohexane ring with a bromine (Br) substituent. - **Reagents/Conditions:** Sodium hydroxide (NaOH) in water (H₂O) with heat. - **Expected Product:** A cyclohexene ring (an alkene). In this reaction, the bromine is expected to be eliminated to form a double bond (alkene). However, under these conditions, the reaction does not proceed. This could be due to the stability of the starting material or unfavorable reaction conditions. --- **Reaction 2:** - **Reactants:** A linear alkane with a methanesulfonate (OMs) substituent. - **Reagents/Conditions:** Sodium hydroxide (NaOH) in acetone. - **Expected Product:** A linear alkene. Here, the methanesulfonate group is expected to leave, allowing the formation of a double bond. The reaction is likely hindered by the solvent choice or the stability of the leaving group. --- **Reaction 3:** - **Reactants:** A cyclohexane ring with a bromine (Br) and an ethyl group. - **Reagents/Conditions:** Sodium hydroxide (NaOH) in water (H₂O) with heat. - **Expected Product:** A cyclohexene ring with an ethyl group (an alkene). Similar to the first reaction, the presence of heat and a strong base typically facilitates elimination. However, this reaction does not occur as expected, possibly due to steric hindrance or poor leaving group ability. --- **Conclusion:** These examples highlight the complexities of chemical reactions, where factors such as the type of solvent, temperature, and nature of the leaving group can dramatically influence the outcome. Understanding these intricacies is crucial for successful reaction planning and execution.
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