1. 2. A CO₂CH3 + OEt H₂C-PPh3 Bu₂N OH CO₂Et CO₂CH3 a = Electrophilic addition b = E2 Elimination c = SN1 Nucleophilic substitution f = Carbonyl nucleophilic addn d = SN2 Nucleophilic substitution e= Electrophilic aromatic substitution g = Nucleophilic subs at carbonyl(acyl Xfer) h = Conjugate (nucleophilic) addn Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters ai for your answers.

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Chapter1: Chemical Foundations
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**1.**

Reactants:
- A cyclopentene derivative with an ester group (CO₂CH₃) attached.
- A β-keto ester compound (with an OEt group).
- **Reagent:** Bu₄N⁺ OH⁻

Product:
- A bicyclic compound with the ester groups CO₂Et and CO₂CH₃.

**2.**

Reactants:
- A long-chain ketone.
- **Reagent:** Phosphorane (-⁻CH₂-PPh₃).

Product:
- An alkene with the same number of carbon atoms as the reactant ketone.
- A by-product: Triphenylphosphine oxide (Ph₃P=O).

**Reaction Mechanisms:**

- **a** = Electrophilic addition
- **b** = E2 Elimination
- **c** = Sₙ1 Nucleophilic substitution
- **d** = Sₙ2 Nucleophilic substitution
- **e** = Electrophilic aromatic substitution
- **f** = Carbonyl nucleophilic addition
- **g** = Nucleophilic substitution at carbonyl (acyl transfer)
- **h** = Conjugate (nucleophilic) addition
- **i** = Other

**Task:**

Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers.
Transcribed Image Text:**1.** Reactants: - A cyclopentene derivative with an ester group (CO₂CH₃) attached. - A β-keto ester compound (with an OEt group). - **Reagent:** Bu₄N⁺ OH⁻ Product: - A bicyclic compound with the ester groups CO₂Et and CO₂CH₃. **2.** Reactants: - A long-chain ketone. - **Reagent:** Phosphorane (-⁻CH₂-PPh₃). Product: - An alkene with the same number of carbon atoms as the reactant ketone. - A by-product: Triphenylphosphine oxide (Ph₃P=O). **Reaction Mechanisms:** - **a** = Electrophilic addition - **b** = E2 Elimination - **c** = Sₙ1 Nucleophilic substitution - **d** = Sₙ2 Nucleophilic substitution - **e** = Electrophilic aromatic substitution - **f** = Carbonyl nucleophilic addition - **g** = Nucleophilic substitution at carbonyl (acyl transfer) - **h** = Conjugate (nucleophilic) addition - **i** = Other **Task:** Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers.
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