### Ranking the Basicity of Nitrogen-Containing Aromatic CompoundsIn organic chemistry, the basicity of nitrogen-containing aromatic compounds can be influenced by various structural factors. The following diagram presents four different nitrogen-containing aromatic compounds labeled A, B, C, and D. These compounds must be ranked in order of decreasing basicity. 1. **Compound A**: - Chemical Structure: A benzene ring with two nitrogen atoms in para positions. - Known as: Pyrimidine2. **Compound B**: - Chemical Structure: A benzene ring with one nitrogen atom. - Known as: Pyridine3. **Compound C**: - Chemical Structure: A five-membered ring with one nitrogen atom and no double bonds. - Known as: Pyrrolidine4. **Compound D**: - Chemical Structure: A five-membered ring with one nitrogen atom and two double bonds. - Known as: Pyrrole### Order of Basicity**Basicity Ranking (from most basic to least basic):**1. **Compound C (Pyrrolidine)**: This compound is such that the nitrogen's lone pair is not part of an aromatic system, making it more available for protonation and hence more basic.2. **Compound B (Pyridine)**: The nitrogen's lone pair is not involved in the aromatic π system, making it moderately basic.3. **Compound A (Pyrimidine)**: Although di-substituted with nitrogen, the lone pairs are still present, and their electron-withdrawing effect slightly reduces basicity compared to pyridine.4. **Compound D (Pyrrole)**: In this compound, the nitrogen's lone pair is part of the aromatic π system, making it less available for protonation and hence less basic.These basicity differences are crucial for understanding reactivity and behavior in chemical reactions and biological systems.

A base is an electron pair donor and basicity is the ability of a base to accept protons. Basicity…

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Rank the following compounds in order of decreasing basicity ( N' NH NH C

Chemistry

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ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

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Chapter1: Chemical Foundations

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Question

### Ranking the Basicity of Nitrogen-Containing Aromatic Compounds

In organic chemistry, the basicity of nitrogen-containing aromatic compounds can be influenced by various structural factors. The following diagram presents four different nitrogen-containing aromatic compounds labeled A, B, C, and D. These compounds must be ranked in order of decreasing basicity.

1. **Compound A**:
- Chemical Structure: A benzene ring with two nitrogen atoms in para positions.
- Known as: Pyrimidine

2. **Compound B**:
- Chemical Structure: A benzene ring with one nitrogen atom.
- Known as: Pyridine

3. **Compound C**:
- Chemical Structure: A five-membered ring with one nitrogen atom and no double bonds.
- Known as: Pyrrolidine

4. **Compound D**:
- Chemical Structure: A five-membered ring with one nitrogen atom and two double bonds.
- Known as: Pyrrole

### Order of Basicity

**Basicity Ranking (from most basic to least basic):**
1. **Compound C (Pyrrolidine)**: This compound is such that the nitrogen's lone pair is not part of an aromatic system, making it more available for protonation and hence more basic.
2. **Compound B (Pyridine)**: The nitrogen's lone pair is not involved in the aromatic π system, making it moderately basic.
3. **Compound A (Pyrimidine)**: Although di-substituted with nitrogen, the lone pairs are still present, and their electron-withdrawing effect slightly reduces basicity compared to pyridine.
4. **Compound D (Pyrrole)**: In this compound, the nitrogen's lone pair is part of the aromatic π system, making it less available for protonation and hence less basic.

These basicity differences are crucial for understanding reactivity and behavior in chemical reactions and biological systems.

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