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Which one of the following compounds is ...

Which one of the following compounds is stable?

A

`CH_(3)CH(OH)_(2)`

B

`(CH_(3))_(2)C(OH)_(2)`

C

`C Cl_(3)CH(OH)_(2)`

D

None of thse

Text Solution

AI Generated Solution

The correct Answer is:
To determine which compound is stable among the given options, we need to analyze the structures and the presence of functional groups in each compound. ### Step-by-Step Solution: 1. **Identify the Compounds**: We have three compounds to analyze: - **Compound 1**: \( \text{CS}_3\text{CH(OH)}_2 \) - **Compound 2**: \( \text{CS}_3\text{C(CS}_3)(\text{OH})_2 \) - **Compound 3**: \( \text{Cl}_3\text{C(OH)}_2 \) 2. **Recognize the Functional Groups**: All three compounds are geminal diols, meaning they have two hydroxyl (–OH) groups attached to the same carbon atom. 3. **Consider Dehydration Reactions**: Each compound can undergo dehydration to form a more stable compound. The dehydration reaction involves the removal of water (H2O) and the formation of a carbonyl compound. 4. **Analyze Electron Donating and Withdrawing Effects**: - **Compound 1** has two methyl groups (–CS3), which are electron-donating groups. This can reduce the stability of the geminal diol because they decrease the partial positive charge on the carbon, making it less electrophilic and less reactive. - **Compound 2** also has two methyl groups, which similarly reduce the stability for the same reasons as Compound 1. - **Compound 3** has three chlorine atoms (–Cl), which are electron-withdrawing groups. This increases the partial positive charge on the carbon, enhancing its electrophilicity and making the compound more stable during the dehydration reaction. 5. **Conclusion**: Since the electron-withdrawing groups in Compound 3 stabilize the geminal diol and facilitate the dehydration reaction, we conclude that **Compound 3** is the most stable among the three options. Therefore, the answer is **Option C**.
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