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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

`(iii)gt(ii)gt(i)`

B

`(ii)gt(i)gt(iii)`

C

`(ii)gt(iii)gt(i)`

D

`(i)gt(ii)gt(iii)`

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 based on the factors that influence stability: the number of carbonyl groups (C=O), the presence of α-hydrogens, and resonance. ### Step-by-Step Solution: 1. **Identify the Compounds:** - (i) `CH2=OH(CH)-CH2=O(C)-CH3` - (ii) `CH3=O(C)-CH2=O(C)-CH3` - (iii) `CH3=OH(C)=CH-O(C)-CH3` 2. **Count the C=O Groups:** - Compound (i) has **1 C=O group**. - Compound (ii) has **2 C=O groups**. - Compound (iii) has **1 C=O group**. **Observation:** Compound (ii) has the highest number of C=O groups, which generally increases stability. 3. **Count the α-Hydrogens:** - For compound (i), the α-carbon has **2 α-hydrogens**. - For compound (ii), the α-carbon has **2 α-hydrogens**. - For compound (iii), the α-carbon has **1 α-hydrogen**. **Observation:** Compounds (i) and (ii) have more α-hydrogens compared to compound (iii). 4. **Evaluate Resonance:** - Compound (i) does not exhibit significant resonance. - Compound (ii) can exhibit resonance due to the presence of two carbonyl groups, allowing electron delocalization. - Compound (iii) has a structure that allows for resonance with the double bond and the adjacent carbonyl. **Observation:** Compound (ii) has the most resonance stabilization due to two carbonyls, while compound (iii) also has resonance but is less stable than (ii). 5. **Order of Stability:** - Based on the analysis: - Compound (ii) is the most stable due to the highest number of C=O groups and resonance. - Compound (iii) is next due to resonance, despite having fewer C=O groups. - Compound (i) is the least stable due to the absence of resonance and fewer C=O groups. ### Final Order of Stability: 1. **(ii)** > 2. **(iii)** > 3. **(i)**

To determine the order of stability of the given tautomeric compounds, we will analyze each compound based on the factors that influence stability: the number of carbonyl groups (C=O), the presence of α-hydrogens, and resonance. ### Step-by-Step Solution: 1. **Identify the Compounds:** - (i) `CH2=OH(CH)-CH2=O(C)-CH3` - (ii) `CH3=O(C)-CH2=O(C)-CH3` - (iii) `CH3=OH(C)=CH-O(C)-CH3` ...
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Knowledge Check

  • The order of stability of the following tautomeric compounds is : CH_(2)=overset(OH)overset(|)C-CH_(2)-underset(I)overset(O)overset(||)C-CH_(3) hArr Ch_(3)-overset(O)overset(||)C-CH_(2)-underset(II)overset(O)overset(||)C-CH_(3) hArr CH_(3)-overset(OH)overset(|)C=CH-underset(III)overset(O)overset(||)C-CH_(3)

    A
    `III gt II gt I`
    B
    `II gt I gt III`
    C
    `II gt III gt I`
    D
    `I gt II gt III`
  • The order of stability of the following tautomeric compounds is underset((I))(CH_(2)=overset(OH)overset(|)(C)-CH_(2)-overset(O)overset(||)(C))-CH_(3)hArr underset((II))(CH_(3)-overset(O)overset(||)(C)-CH_(2)-overset(O)overset(||)(C))-CH_(3)hArr underset((III))(CH_(3)-overset(OH)overset(|)(C)=CH -overset(O)overset(||)(C)-CH_(3))

    A
    `II gt III gt I`
    B
    `I gt II gt III`
    C
    `III gt II gt I`
    D
    `II gt I gt III`
  • The order of stability of the following tautomeric compound is I. CH_(2)=overset(OH)overset("| ")"C "-CH_(2)-overset(O)overset(||)C-CH_(3) II. CH_(3)-overset(O)overset(||)C-CH_(2)-overset(O)overset(||)C-CH_(2) 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`
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