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5. Draw the major organic product(s) of each reaction and specify the most likel mechanism by which each is formed. a) b) C/ + CH3OH + OTS OMs Methanol + NaOEt 01 95 °C EtOH NOO

5. Draw the major organic product(s) of each reaction and specify the most likel mechanism by which each is formed. a) b) C/ + CH3OH + OTS OMs Methanol + NaOEt 01 95 °C EtOH NOO

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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
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**Question 5:** Draw the major organic product(s) of each reaction and specify the most likely mechanism by which each is formed. **(a) Reaction:** - Reactants: - Cyclohexyl chloride (a cyclohexane ring with a chlorine substituent). - Methanol (\(CH_3OH\)). - Solvent: Methanol. - Description: This reaction likely proceeds through an \(S_N1\) mechanism due to the potential formation of a stable carbocation intermediate after the departure of the chloride ion. Methanol can then act as a nucleophile and attack the carbocation, leading to the formation of a methoxycyclohexane product. **(b) Reaction:** - Reactants: - A tosylate attached to an isopropyl group (\(CH_3CH(OTs)CH_3\)). - Sodium ethoxide (\(NaOEt\)). - Conditions: 95°C in ethanol (\(EtOH\)). - Description: This reaction is likely an \(E2\) elimination. Sodium ethoxide acts as a strong base, abstracting a proton from the isopropyl group. This results in the formation of a double bond and the expulsion of the tosylate group, yielding propene as the major product. **(c) Reaction:** - Reactants: - A cyclopropyl methyl methanesulfonate (\(OMs\)) group. - Potassium cyclopropanecarboxylate (\(K^+O^-\)). - Solvent: DMSO. - Description: This reaction may proceed through an \(S_N2\) mechanism, where the cyclopropane carboxylate ion serves as a strong nucleophile, attacking the electrophilic carbon where the mesylate is attached. The \(OMs\) (mesylate) group leaves, resulting in a nucleophilic substitution to produce the corresponding ether. These descriptions provide an overview of the likely mechanisms for each reaction based on the reagents, conditions, and typical organic chemistry reactions involved.
Transcribed Image Text:**Question 5:** Draw the major organic product(s) of each reaction and specify the most likely mechanism by which each is formed. **(a) Reaction:** - Reactants: - Cyclohexyl chloride (a cyclohexane ring with a chlorine substituent). - Methanol (\(CH_3OH\)). - Solvent: Methanol. - Description: This reaction likely proceeds through an \(S_N1\) mechanism due to the potential formation of a stable carbocation intermediate after the departure of the chloride ion. Methanol can then act as a nucleophile and attack the carbocation, leading to the formation of a methoxycyclohexane product. **(b) Reaction:** - Reactants: - A tosylate attached to an isopropyl group (\(CH_3CH(OTs)CH_3\)). - Sodium ethoxide (\(NaOEt\)). - Conditions: 95°C in ethanol (\(EtOH\)). - Description: This reaction is likely an \(E2\) elimination. Sodium ethoxide acts as a strong base, abstracting a proton from the isopropyl group. This results in the formation of a double bond and the expulsion of the tosylate group, yielding propene as the major product. **(c) Reaction:** - Reactants: - A cyclopropyl methyl methanesulfonate (\(OMs\)) group. - Potassium cyclopropanecarboxylate (\(K^+O^-\)). - Solvent: DMSO. - Description: This reaction may proceed through an \(S_N2\) mechanism, where the cyclopropane carboxylate ion serves as a strong nucleophile, attacking the electrophilic carbon where the mesylate is attached. The \(OMs\) (mesylate) group leaves, resulting in a nucleophilic substitution to produce the corresponding ether. These descriptions provide an overview of the likely mechanisms for each reaction based on the reagents, conditions, and typical organic chemistry reactions involved.
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