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The correct order of acidic strength of ...

The correct order of acidic strength of the following is
(I) Oxalic acid `HOOC-COOH`
(II) Malonic acid
`HOOC-CH_(2)-COOH`
(III) Succinic acid
`HOOC-(CH_(2))_(2)-COOH`
(IV) Glutaric acid
`HOOC-(CH_(2))_(3)-COOH`

A

`I gt II gt III gt IV`

B

`I gt III gt II gt IV`

C

`IV gt III gt II gt I`

D

`IV gt II gt III gt I`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct order of acidic strength among the given dicarboxylic acids, we need to analyze the stability of their conjugate bases after they lose a proton (H⁺). The conjugate base of a dicarboxylic acid is a carboxylate ion, which is stabilized by electron-withdrawing groups and destabilized by electron-donating groups (like alkyl groups). ### Step-by-Step Solution: 1. **Identify the Compounds:** - (I) Oxalic acid: `HOOC-COOH` - (II) Malonic acid: `HOOC-CH₂-COOH` - (III) Succinic acid: `HOOC-(CH₂)₂-COOH` - (IV) Glutaric acid: `HOOC-(CH₂)₃-COOH` 2. **Understand the Effect of Alkyl Groups:** - Alkyl groups exert a +I (inductive) effect, which increases electron density on the carboxylate ion formed after deprotonation. This destabilizes the conjugate base, leading to a decrease in acidic strength. 3. **Analyze Each Acid:** - **Oxalic Acid (I):** Has no alkyl groups, so it has the highest acidic strength because its conjugate base is the most stabilized. - **Malonic Acid (II):** Contains one alkyl group (CH₂), which exerts a +I effect, thus reducing acidic strength compared to oxalic acid. - **Succinic Acid (III):** Contains two alkyl groups (CH₂-CH₂), further increasing the +I effect and reducing acidic strength compared to malonic acid. - **Glutaric Acid (IV):** Contains three alkyl groups (CH₂-CH₂-CH₂), which will exert the most +I effect, making it the least acidic. 4. **Order of Acidic Strength:** - Based on the analysis, the order of acidic strength from strongest to weakest is: - (I) Oxalic acid > (II) Malonic acid > (III) Succinic acid > (IV) Glutaric acid. 5. **Final Answer:** - The correct order of acidic strength is: - **Oxalic acid > Malonic acid > Succinic acid > Glutaric acid.**
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Why is CH_(2)=CH-COOH a stronger acid than CH_(3)CH_(2)COOH ?

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Knowledge Check

  • Common name of HOOC-(CH_(2))_(4)-COOH is

    A
    glutaric acid.
    B
    adipic acid.
    C
    succinic acid.
    D
    malonic acid.

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    A
    `IIltIVltIltIII`
    B
    `IVltIltIIIltII`
    C
    `fIVltIltIIltIII`
    D
    `IltIVltIIIltII`

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    A
    `I lt II lt III`
    B
    `I lt III lt II `
    C
    `III lt II lt I`
    D
    `II lt I lt III`

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