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Consider the following carbanions (i) ...

Consider the following carbanions
`(i) CH_(3)- overset(Ө)CH_(2)" "(ii) CH_(2) = overset(Ө)CH" "(iii) CH -= overset(Ө)C `
Correct order of stability of these carbanions in decreasing order is

A

`1 gt 2 gt 3`

B

`2 gt 1 gt 3`

C

`3 gt 2 gt 1`

D

`3 gt 1 gt 2`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct order of stability of the given carbanions, we will analyze the hybridization and s-character of each carbanion: 1. **Identify the Hybridization of Each Carbanion:** - **(i) CH₃-Ø-CH₂**: The carbon atom with the carbanion has four bonds (three from CH₃ and one from CH₂) and is **sp³ hybridized**. - **(ii) CH₂=Ø-CH**: The carbon atom with the carbanion has three bonds (two from CH₂ and one from CH) and is **sp² hybridized**. - **(iii) CH≡Ø-C**: The carbon atom with the carbanion has two bonds (one from CH and one from the triple bond) and is **sp hybridized**. 2. **Determine the s-character of Each Hybridization:** - **sp³ hybridization** has **25% s-character**. - **sp² hybridization** has **33% s-character**. - **sp hybridization** has **50% s-character**. 3. **Stability Analysis:** - Carbanions with higher s-character are more stable because the electrons are held closer to the nucleus. Therefore, the stability order based on the s-character is as follows: - **(iii) CH≡Ø-C** (sp hybridized, 50% s-character) - Most stable - **(ii) CH₂=Ø-CH** (sp² hybridized, 33% s-character) - Moderately stable - **(i) CH₃-Ø-CH₂** (sp³ hybridized, 25% s-character) - Least stable 4. **Final Order of Stability:** - The correct order of stability of the carbanions in decreasing order is: - **(iii) > (ii) > (i)** Thus, the final answer is: **(iii) > (ii) > (i)**.
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Knowledge Check

  • Consider the following species : (A) overset(ө)H" (B) " CH_(3)-overset(ө)(O) " (C) " overset(ө)(C)H_(3) " (D) " overset(ө)(N)H_(2) Arrange these species in their decreasing order of nucleophilicity.

    A
    `C gt D gt B gt A`
    B
    `B gt A gt C gt D`
    C
    `A gt B gt C gt D`
    D
    `C gt A gt B gt D`

  • The order of stability of the following carbocations CH_2 = underset((I))overset(+)CH - CH_2 , CH_3 - underset((II))CH_2 - overset(+)(CH_2)

    A
    III gt II gt I
    B
    II gt III gt I
    C
    I gt II gt III
    D
    III gt I gt II

  • The order of decreasing stability of the cations is : (I) CH_(3) overset(+)(CH)CH_(3) " "(II) CH_(2) overset(+)(CH)OCH_(3) " " (III) CH_(3) overset(+))CH+COCH_(3)

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

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