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
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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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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