Draw the missing products and/or reagents in the following multistep synthesis. OH Select to Draw NaH CH3CH₂I Select to Draw 1. Hg(OAc)2, H₂O 2. NaBH4, NaOH Select to Draw 00

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.28P
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**Multistep Synthesis Task**

**Objective:**  
Draw the missing products and/or reagents in the following multistep synthesis.

**Initial Compound:**  
- A structure with a benzene ring connected to a carbon chain with an alcohol (OH) group and an alkene group (isopropenyl group).

**Intermediate Steps:**

1. **Missing Reaction/Product:**
   - There is a box labeled "Select to Draw" connected by an arrow.

2. **Reagents for Second Step:**
   - 1. Hg(OAc)₂, H₂O
   - 2. NaBH₄, NaOH
   
   This sequence indicates an oxymercuration-demercuration reaction, which typically converts alkenes to alcohols.

3. **Intermediate Compound:**
   - A compound featuring a thiol group (S) in place of the oxygen from the alcohol, attached to the carbon chain, and maintaining the aromatic ring.

4. **Reagents for Third Step:**
   - NaH (sodium hydride), CH₃CH₂I (ethyl iodide)

5. **Missing Reaction/Product:**
   - Another box labeled "Select to Draw" connected by an arrow.

**Graphical Explanation:**

- The diagram begins with a clear structure (an alcohol and alkene on an aromatic ring) and requires users to deduce or draw the intermediate steps and final products using provided reagents.
- The process involves an initial transformation, oxymercuration-demercuration, and then further alkylation using sodium hydride and ethyl iodide.

*Note: The complexity of the reactions requires understanding organic chemistry concepts, including reaction mechanisms and reagent functions.*
Transcribed Image Text:**Multistep Synthesis Task** **Objective:** Draw the missing products and/or reagents in the following multistep synthesis. **Initial Compound:** - A structure with a benzene ring connected to a carbon chain with an alcohol (OH) group and an alkene group (isopropenyl group). **Intermediate Steps:** 1. **Missing Reaction/Product:** - There is a box labeled "Select to Draw" connected by an arrow. 2. **Reagents for Second Step:** - 1. Hg(OAc)₂, H₂O - 2. NaBH₄, NaOH This sequence indicates an oxymercuration-demercuration reaction, which typically converts alkenes to alcohols. 3. **Intermediate Compound:** - A compound featuring a thiol group (S) in place of the oxygen from the alcohol, attached to the carbon chain, and maintaining the aromatic ring. 4. **Reagents for Third Step:** - NaH (sodium hydride), CH₃CH₂I (ethyl iodide) 5. **Missing Reaction/Product:** - Another box labeled "Select to Draw" connected by an arrow. **Graphical Explanation:** - The diagram begins with a clear structure (an alcohol and alkene on an aromatic ring) and requires users to deduce or draw the intermediate steps and final products using provided reagents. - The process involves an initial transformation, oxymercuration-demercuration, and then further alkylation using sodium hydride and ethyl iodide. *Note: The complexity of the reactions requires understanding organic chemistry concepts, including reaction mechanisms and reagent functions.*
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