Which of the following compounds is a stronger base: (CH;)4NOH or (CH;);NHOH? Explain.

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**Question:** Which of the following compounds is a stronger base: \((CH_3)_4NOH\) or \((CH_3)_3NHOH\)? Explain.

### Explanation for an Educational Website
Both compounds are bases and contain nitrogen atoms. The basicity of a compound can often be predicted by examining the presence of nitrogen and its surrounding groups.

1. **Tetramethylammonium Hydroxide (\((CH_3)_4NOH\)):** 
   - This compound is a quaternary ammonium hydroxide.
   - It has four methyl groups attached to the nitrogen, making it a strong base.
   - The lack of hydrogen atoms directly attached to the nitrogen reduces the possibility of hydrogen bonding, often increasing basicity.

2. **Trimethylhydroxylamine (\((CH_3)_3NHOH\)):**
   - This compound has three methyl groups and one hydroxyl group attached to the nitrogen.
   - The presence of the hydroxyl group can lead to hydrogen bonding, which might slightly reduce its basic nature compared to \((CH_3)_4NOH\).

**Conclusion:**
Typically, \((CH_3)_4NOH\) would be the stronger base because the presence of more alkyl groups that stabilize the positive charge on the nitrogen makes it a better electron pair donor. The presence of the hydroxyl group in \((CH_3)_3NHOH\) might cause hydrogen bonding, which can slightly decrease its basicity.
Transcribed Image Text:### Text Transcription **Question:** Which of the following compounds is a stronger base: \((CH_3)_4NOH\) or \((CH_3)_3NHOH\)? Explain. ### Explanation for an Educational Website Both compounds are bases and contain nitrogen atoms. The basicity of a compound can often be predicted by examining the presence of nitrogen and its surrounding groups. 1. **Tetramethylammonium Hydroxide (\((CH_3)_4NOH\)):** - This compound is a quaternary ammonium hydroxide. - It has four methyl groups attached to the nitrogen, making it a strong base. - The lack of hydrogen atoms directly attached to the nitrogen reduces the possibility of hydrogen bonding, often increasing basicity. 2. **Trimethylhydroxylamine (\((CH_3)_3NHOH\)):** - This compound has three methyl groups and one hydroxyl group attached to the nitrogen. - The presence of the hydroxyl group can lead to hydrogen bonding, which might slightly reduce its basic nature compared to \((CH_3)_4NOH\). **Conclusion:** Typically, \((CH_3)_4NOH\) would be the stronger base because the presence of more alkyl groups that stabilize the positive charge on the nitrogen makes it a better electron pair donor. The presence of the hydroxyl group in \((CH_3)_3NHOH\) might cause hydrogen bonding, which can slightly decrease its basicity.
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