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Arrange the carbonions, (CH(3))(3)over...

Arrange the carbonions,
`(CH_(3))_(3)overset(-)C, overset(-)C Cl_(3), (CH_(3))_(2) overset(-)CH, C_(6)H_(5)overset(-)CH_(2)` in order of their decreasing stability

A

`(CH_(3))_(2)overset(-)CH gt overset(-)C Cl_(3) gt C_(6)H_(5)overset(-)CH_(2) gt (CH_(3))_(3)overset(-)C`

B

`overset(-)C Cl_(3) gt C_(6)H_(5)overset(-)CH_(2) gt (CH_(3))_(2)overset(-)CH gt (CH_(3))_(3)overset(-)C`

C

`(CH_(3))_(3) overset(-)C gt (CH_(3))_(2)overset(-)CHgt C_(6)H_(5)overset(-)CH_(2) gt overset(-)C Cl _(3)`

D

`C_(6)H_(5)overset(-)CH_(2) gt overset(-)C Cl_(3) gt (CH_(3))_(3) overset(-)C gt (CH_(3))_(2) overset(-)CH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the stability of the given carbanions, we need to analyze the effects of substituents on the carbon atom that carries the negative charge. The stability of carbanions is influenced by inductive effects and resonance. ### Step-by-Step Solution: 1. **Identify the Structures of the Carbanions**: - (CH₃)₃C⁻: This is a tert-butyl carbanion where the negative charge is on a carbon atom bonded to three methyl groups. - CCl₃⁻: This is a trichloro carbanion where the negative charge is on a carbon atom bonded to three chlorine atoms. - (CH₃)₂CH⁻: This is an isopropyl carbanion where the negative charge is on a carbon atom bonded to two methyl groups and one hydrogen. - C₆H₅CH₂⁻: This is a benzyl carbanion where the negative charge is on a carbon atom bonded to a benzene ring and a hydrogen atom. 2. **Analyze the Effects on Stability**: - **(CH₃)₃C⁻**: The three methyl groups exert a +I (inductive) effect, which increases the electron density at the negatively charged carbon, making it less stable. - **CCl₃⁻**: The three chlorine atoms exert a -I (inductive) effect, which decreases the electron density at the negatively charged carbon, making it more stable. - **(CH₃)₂CH⁻**: The two methyl groups also exert a +I effect, which increases the electron density at the negatively charged carbon, but less so than in the case of (CH₃)₃C⁻. - **C₆H₅CH₂⁻**: The negative charge can be delocalized through resonance with the benzene ring, significantly stabilizing the carbanion. 3. **Rank the Carbanions by Stability**: - **Most Stable**: CCl₃⁻ (due to -I effect from Cl atoms) - **Second Stable**: C₆H₅CH₂⁻ (due to resonance stabilization) - **Third Stable**: (CH₃)₂CH⁻ (due to +I effect from two methyl groups) - **Least Stable**: (CH₃)₃C⁻ (due to +I effect from three methyl groups) ### Final Order of Stability: 1. CCl₃⁻ 2. C₆H₅CH₂⁻ 3. (CH₃)₂CH⁻ 4. (CH₃)₃C⁻
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MOTION-GOC-Exercise - 2 (Level - I)
  1. In which of the following pairs, first species is more stable than sec...

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  2. The order of stability of the following carbanion is (I) CH(3)overse...

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  3. Arrange the carbonions, (CH(3))(3)overset(-)C, overset(-)C Cl(3), (C...

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  4. There are three canonical structures of napthalene. Examine them and f...

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  5. Which of the following has longest C – O bond:

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  6. Among the following molecules, the correct order of C - C bond length ...

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  7. In which of the following molecules pi-electron density in ring is max...

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  8. Which of these cyclopropene systems is aromatic

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  9. Which of these species is anti-aromatic ?

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  10. Which of the following compouds is not aromatic

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  11. The most stable canonical structure of this molecule is

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  12. The most stable canonical structure of this molecule is

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  13. The barrier for rotation about the indicated bonds Will be maximum i...

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  14. Identify the odd species out Which of the species among the following ...

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  15. Which of the following heterocyclic compounds would have aromatic char...

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  16. Which one of the following carbonyl compound when treated with dilute ...

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  17. The order of the rate of formation of carbocations from the following ...

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  18. Write correct order of reactivity of following halogen derivatives tow...

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  19. Which of the following species is not aromatic ?

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  20. The aromatic character is maximum in which of these three compounds ?

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