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Provide all possible organometallic nucleophile and carbonyl electrophile combinations that would lead directly to the given product after an acidic workup step. Please format your answers as we did in lecture using a retrosynthetic arrow. Example: Но Ме „MgBr „Me Me Me 1. OH 2. HO, 3. Me HO Me Me

Provide all possible organometallic nucleophile and carbonyl electrophile combinations that would lead directly to the given product after an acidic workup step. Please format your answers as we did in lecture using a retrosynthetic arrow. Example: Но Ме „MgBr „Me Me Me 1. OH 2. HO, 3. Me HO Me Me

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
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--- **Title: Organometallic Nucleophile and Carbonyl Electrophile Combinations** **Objective:** To identify all possible combinations of organometallic nucleophiles and carbonyl electrophiles that lead directly to given products after an acidic workup step. Follow the retrosynthetic analysis method learned in lectures. **Instructions:** Reflect on how these reactions employ retrosynthetic thinking to deduce precursor materials. **Example Analysis:** - **Product:** A tertiary alcohol featuring a phenyl group and two methyl groups. - **Retrosynthetic Route:** - Convert the alcohol to a carbonyl compound and a Grignard reagent. **Example:** ![Example Reaction] - Grignard Reagent: Bromobenzene magnesium bromide (phenyl MgBr) - Carbonyl Electrophile: Acetone (dimethyl ketone) **Exercises:** 1. **Compound 1:** - Structure: Cyclohexanol derivative with a terminal alkene. - Task: Identify possible precursor combinations. 2. **Compound 2:** - Structure: Cyclohexanol with a butyl side chain. - Task: Illustrate the breakdown into reactants. 3. **Compound 3:** - Structure: Complex tertiary alcohol with multiple methyl groups. - Task: Determine the organometallic and carbonyl precursors. **Graph/Diagram Description:** - **Structures:** Displayed are structural formulas showing functional groups pertinent for retrosynthetic analysis. - **Reaction Arrow:** A retrosynthetic arrow indicates the backward reasoning used to identify potential reactants. **Remember:** Each structure provides crucial information for selecting appropriate nucleophiles and electrophiles. Utilize the organometallic reagents' nucleophilic nature and the electrophilicity of carbonyl compounds to map possible synthesis routes. ---
Transcribed Image Text:--- **Title: Organometallic Nucleophile and Carbonyl Electrophile Combinations** **Objective:** To identify all possible combinations of organometallic nucleophiles and carbonyl electrophiles that lead directly to given products after an acidic workup step. Follow the retrosynthetic analysis method learned in lectures. **Instructions:** Reflect on how these reactions employ retrosynthetic thinking to deduce precursor materials. **Example Analysis:** - **Product:** A tertiary alcohol featuring a phenyl group and two methyl groups. - **Retrosynthetic Route:** - Convert the alcohol to a carbonyl compound and a Grignard reagent. **Example:** ![Example Reaction] - Grignard Reagent: Bromobenzene magnesium bromide (phenyl MgBr) - Carbonyl Electrophile: Acetone (dimethyl ketone) **Exercises:** 1. **Compound 1:** - Structure: Cyclohexanol derivative with a terminal alkene. - Task: Identify possible precursor combinations. 2. **Compound 2:** - Structure: Cyclohexanol with a butyl side chain. - Task: Illustrate the breakdown into reactants. 3. **Compound 3:** - Structure: Complex tertiary alcohol with multiple methyl groups. - Task: Determine the organometallic and carbonyl precursors. **Graph/Diagram Description:** - **Structures:** Displayed are structural formulas showing functional groups pertinent for retrosynthetic analysis. - **Reaction Arrow:** A retrosynthetic arrow indicates the backward reasoning used to identify potential reactants. **Remember:** Each structure provides crucial information for selecting appropriate nucleophiles and electrophiles. Utilize the organometallic reagents' nucleophilic nature and the electrophilicity of carbonyl compounds to map possible synthesis routes. ---
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