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A compound containing two-OH groups atta...

A compound containing two-OH groups attached with same carbon dehydrates easily, but with which on of the following is its stable ?

A

`CH_(3)-`

B

`H_(3) C-CH_(2) -`

C

`Cl_(3) C-`

D

None of these

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the stability of a compound with two -OH groups attached to the same carbon, we will analyze the factors affecting the stability of such compounds. ### Step-by-Step Solution: 1. **Understanding the Structure**: - The compound in question has two -OH (hydroxyl) groups attached to the same carbon atom. This structure is known as a geminal diol. 2. **Dehydration of Geminal Diols**: - Geminal diols are known to dehydrate easily to form carbonyl compounds (C=O). This occurs because the presence of two hydroxyl groups on the same carbon creates significant repulsion between the lone pairs of electrons on the oxygen atoms. 3. **Analyzing Stability Factors**: - When two -OH groups are present on the same carbon, the increased lone pair-lone pair (Lp-Lp) repulsion destabilizes the compound, leading to dehydration and the formation of a carbonyl compound. 4. **Evaluating Different Substituents**: - We need to evaluate the stability of the geminal diol with different substituents: - **Case 1: CH3OHCH3**: This compound will also dehydrate easily as there are no stabilizing factors. - **Case 2: C2H5OH**: Similar reasoning applies; it will also dehydrate easily. - **Case 3: CCl3OH**: The presence of chlorine, being highly electronegative, can lead to intramolecular hydrogen bonding. This bonding stabilizes the structure and reduces the tendency to dehydrate. 5. **Conclusion**: - Among the options provided, the compound with the CCl3 substituent is the most stable due to the formation of intramolecular hydrogen bonds, which counteract the destabilizing effects of the two -OH groups. ### Final Answer: The compound with the CCl3 substituent is stable, making the correct answer **C (CCl3)**.
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