4. Complete the outlined reaction sequence by drawing structures for the major products expected. Zn(Hg) Ck, 1 eq. KOH HCI(aq) UV-light heat AICa

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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### Problem 4: Complete the Reaction Sequence

#### Description:
You are required to complete the outlined reaction sequence by drawing structures for the major products expected. Below is the reaction sequence provided:

1. Starting compound: Benzene
2. Reagent: AlCl₃
3. Intermediate Product (To be drawn): ?
4. Reagents: Zn(Hg), HCl(aq)
5. Intermediate Product (To be drawn): ?
6. Reagents: Cl₂, 1 eq., UV-light
7. Intermediate Product (To be drawn): ?
8. Reagents: KOH, heat
9. Final Product (To be drawn): ?

#### Explanation:

1. **Friedel-Crafts Acylation**: 
   - **Reagent**: AlCl₃ 
   - **Reactant**: Acyl chloride (benzoyl chloride)
   - **Intermediate Product**: Benzoylbenzene (Phenylacetophenone)

2. **Clemmensen Reduction**:
   - **Reagent**: Zn(Hg) with HCl(aq)
   - **Reactant**: Benzoylbenzene
   - **Intermediate Product**: Alkylbenzene (Ethylbenzene)

3. **Halogenation**:
   - **Reagent**: Cl₂, 1 eq. under UV-light
   - **Reactant**: Ethylbenzene
   - **Intermediate Product**: Chloroethylbenzene (1-Chloroethylbenzene)

4. **Dehydrohalogenation**:
   - **Reagent**: KOH with heat
   - **Reactant**: Chloroethylbenzene
   - **Final Product**: Styrene (Phenylethene)

Make sure to draw the skeletal structures for each intermediate product and the final product to complete the sequence as required by the problem.
Transcribed Image Text:### Problem 4: Complete the Reaction Sequence #### Description: You are required to complete the outlined reaction sequence by drawing structures for the major products expected. Below is the reaction sequence provided: 1. Starting compound: Benzene 2. Reagent: AlCl₃ 3. Intermediate Product (To be drawn): ? 4. Reagents: Zn(Hg), HCl(aq) 5. Intermediate Product (To be drawn): ? 6. Reagents: Cl₂, 1 eq., UV-light 7. Intermediate Product (To be drawn): ? 8. Reagents: KOH, heat 9. Final Product (To be drawn): ? #### Explanation: 1. **Friedel-Crafts Acylation**: - **Reagent**: AlCl₃ - **Reactant**: Acyl chloride (benzoyl chloride) - **Intermediate Product**: Benzoylbenzene (Phenylacetophenone) 2. **Clemmensen Reduction**: - **Reagent**: Zn(Hg) with HCl(aq) - **Reactant**: Benzoylbenzene - **Intermediate Product**: Alkylbenzene (Ethylbenzene) 3. **Halogenation**: - **Reagent**: Cl₂, 1 eq. under UV-light - **Reactant**: Ethylbenzene - **Intermediate Product**: Chloroethylbenzene (1-Chloroethylbenzene) 4. **Dehydrohalogenation**: - **Reagent**: KOH with heat - **Reactant**: Chloroethylbenzene - **Final Product**: Styrene (Phenylethene) Make sure to draw the skeletal structures for each intermediate product and the final product to complete the sequence as required by the problem.
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ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning