a) Para, ortho and meta nitrophenol are constitutional isomers of one another that all vary in the position of the nitro group around the ring relative to the hydroxy group. Whereas the pKa of both para and ortho-nitrophenol is virtually identical at 7.1 and 7.2 respectively, the pka of meta-nitrophenol is very different at pka = 9.3. ОН OH ОН NO2 'NO2 NO2 Ortho-nitrophenol meta-nitrophenol para-nitrophenol 1) State whether meta-nitrophenol is more or less acidic compared to ortho- or para- nitrophenol.

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# 2. Resonance

**a)** Para, ortho, and meta nitrophenol are constitutional isomers of one another that all vary in the position of the nitro group around the ring relative to the hydroxy group.

Whereas the pKa of both para and ortho-nitrophenol is virtually identical at 7.1 and 7.2 respectively, the pKa of meta-nitrophenol is very different at pKa = 9.3.

### Structural Diagrams:
- **Ortho-nitrophenol**: The nitro group (NO₂) is adjacent to the hydroxy group (OH).
- **Meta-nitrophenol**: The nitro group (NO₂) is one carbon away from the hydroxy group (OH), not directly adjacent.
- **Para-nitrophenol**: The nitro group (NO₂) is opposite the hydroxy group (OH) on the benzene ring.

### Questions:
1. **State whether meta-nitrophenol is more or less acidic compared to ortho- or para-nitrophenol.**

2. **Using your knowledge of resonance, structure, and electronegativity, explain the difference in pKa of the three different constitutional isomers.**
Transcribed Image Text:# 2. Resonance **a)** Para, ortho, and meta nitrophenol are constitutional isomers of one another that all vary in the position of the nitro group around the ring relative to the hydroxy group. Whereas the pKa of both para and ortho-nitrophenol is virtually identical at 7.1 and 7.2 respectively, the pKa of meta-nitrophenol is very different at pKa = 9.3. ### Structural Diagrams: - **Ortho-nitrophenol**: The nitro group (NO₂) is adjacent to the hydroxy group (OH). - **Meta-nitrophenol**: The nitro group (NO₂) is one carbon away from the hydroxy group (OH), not directly adjacent. - **Para-nitrophenol**: The nitro group (NO₂) is opposite the hydroxy group (OH) on the benzene ring. ### Questions: 1. **State whether meta-nitrophenol is more or less acidic compared to ortho- or para-nitrophenol.** 2. **Using your knowledge of resonance, structure, and electronegativity, explain the difference in pKa of the three different constitutional isomers.**
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