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The order of stability of the following ...

The order of stability of the following tautomeric compounds is
(i). `CH_(2)=overset(OH)overset(|)(CH)-CH_(2)-overset(O)overset(||)(C)-CH_(3)hArr`
(ii). `CH_(3)-overset(O)overset(||)(C)-CH_(2)-overset(O)overset(||)(C)-CH_(3)hArr`
(iii). `CH_(3)-overset(OH)overset(|)(C)=CH-overset(O)overset(||)(C)-CH_(3)`

A

`I gt II gt III`

B

`III gt II gt I`

C

`II gt I gt III`

D

`II gt III gt I`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the order of stability of the given tautomeric compounds, we will analyze each compound step by step. ### Step 1: Identify the Structures 1. **Compound (i)**: `CH2=CHO-CH2-C(=O)-CH3` - This is an enol form with a hydroxyl group (-OH) and a double bond. 2. **Compound (ii)**: `CH3-C(=O)-CH2-C(=O)-CH3` - This is a keto form with two carbonyl groups (C=O). 3. **Compound (iii)**: `CH3-CHO=CH-C(=O)-CH3` - This compound has a hydroxyl group and a double bond, with a carbonyl group that is conjugated with the double bond. ### Step 2: Analyze Stability - **Keto vs Enol Forms**: Generally, keto forms are more stable than enol forms due to the greater strength of the C=O double bond compared to the C=C double bond and the presence of hydrogen bonding in the keto form. - **Compound (i)**: The presence of the enol form makes it less stable compared to the keto form. - **Compound (ii)**: This compound is entirely in the keto form, which is typically the most stable configuration due to the presence of two carbonyl groups. - **Compound (iii)**: This compound has conjugation between the carbonyl group and the double bond, which allows for electron delocalization, increasing its stability compared to simple enol forms. ### Step 3: Compare Stability 1. **Compound (iii)**: Most stable due to conjugation and delocalization of electrons. 2. **Compound (ii)**: Stable due to being in the keto form with two carbonyl groups. 3. **Compound (i)**: Least stable as it is in the enol form. ### Conclusion The order of stability of the given tautomeric compounds is: **(iii) > (ii) > (i)**

To determine the order of stability of the given tautomeric compounds, we will analyze each compound step by step. ### Step 1: Identify the Structures 1. **Compound (i)**: `CH2=CHO-CH2-C(=O)-CH3` - This is an enol form with a hydroxyl group (-OH) and a double bond. 2. **Compound (ii)**: `CH3-C(=O)-CH2-C(=O)-CH3` - This is a keto form with two carbonyl groups (C=O). ...
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