HNO3 H₂SO4 NO₂ CI AICI 3 NO₂

Chemistry
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ISBN:9781305957404
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### Nitration and Friedel-Crafts Alkylation of Benzene

**Reaction Scheme:**

1. **First Reaction - Nitration:**
   - **Reactants:** Benzene is reacted with a mixture of nitric acid (HNO₃) and sulfuric acid (H₂SO₄).
   - **Product:** Nitrobenzene is formed. The benzene ring now has a nitro group (NO₂) attached to it.

2. **Second Reaction - Friedel-Crafts Alkylation:**
   - **Reactants:** Nitrobenzene is further reacted with 1-chloropropane (an alkyl chloride, written as a three-carbon chain with Cl at one end) in the presence of aluminum chloride (AlCl₃), a catalyst.
   - **Product:** The final product is an alkylated nitrobenzene where an additional propyl group is attached to the benzene ring.

**Mechanism Overview:**

- **Nitration:** This reaction involves the formation of a nitronium ion (NO₂⁺) in the mixture of nitric and sulfuric acids, which then electrophilically substitutes a hydrogen atom on the benzene ring, forming nitrobenzene.
  
- **Friedel-Crafts Alkylation:** The aluminum chloride catalyst helps generate a carbocation from the alkyl chloride, which acts as an electrophile and substitutes another hydrogen atom on the nitrobenzene, resulting in an alkyl-substituted nitrobenzene.

Both steps show classic examples of electrophilic aromatic substitution, demonstrating the reactivity of benzene in forming more complex aromatic compounds. This sequence is commonly used in organic synthesis to introduce functional groups onto aromatic rings.
Transcribed Image Text:### Nitration and Friedel-Crafts Alkylation of Benzene **Reaction Scheme:** 1. **First Reaction - Nitration:** - **Reactants:** Benzene is reacted with a mixture of nitric acid (HNO₃) and sulfuric acid (H₂SO₄). - **Product:** Nitrobenzene is formed. The benzene ring now has a nitro group (NO₂) attached to it. 2. **Second Reaction - Friedel-Crafts Alkylation:** - **Reactants:** Nitrobenzene is further reacted with 1-chloropropane (an alkyl chloride, written as a three-carbon chain with Cl at one end) in the presence of aluminum chloride (AlCl₃), a catalyst. - **Product:** The final product is an alkylated nitrobenzene where an additional propyl group is attached to the benzene ring. **Mechanism Overview:** - **Nitration:** This reaction involves the formation of a nitronium ion (NO₂⁺) in the mixture of nitric and sulfuric acids, which then electrophilically substitutes a hydrogen atom on the benzene ring, forming nitrobenzene. - **Friedel-Crafts Alkylation:** The aluminum chloride catalyst helps generate a carbocation from the alkyl chloride, which acts as an electrophile and substitutes another hydrogen atom on the nitrobenzene, resulting in an alkyl-substituted nitrobenzene. Both steps show classic examples of electrophilic aromatic substitution, demonstrating the reactivity of benzene in forming more complex aromatic compounds. This sequence is commonly used in organic synthesis to introduce functional groups onto aromatic rings.
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