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Basics of Organic Chemistry question

2009 · Shift 0 · Q5
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  5. /2009 · Shift 0 · Q5

Basics of Organic Chemistry question

2009 · Shift 0 · Q5

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Arrange the carbanions, (CH3)3C‾{(C{H_3})_3}\overline C(CH3​)3​C, C‾Cl3\overline C C{l_3}CCl3​, (CH3)2C‾H{(C{H_3})_2}\overline C H(CH3​)2​CH, C6H5C‾H2{C_6}{H_5}\overline C H{}_2C6​H5​CH2​ in order of their decreasing stability :
  1. A
    (CH3)2C‾H{(C{H_3})_2}\overline C H(CH3​)2​CH>C‾Cl3\overline C C{l_3}CCl3​>C6H5C‾H2{C_6}{H_5}\overline C H{}_2C6​H5​CH2​>(CH3)3C‾{(C{H_3})_3}\overline C(CH3​)3​C
  2. B
    C‾Cl3\overline C C{l_3}CCl3​>C6H5C‾H2{C_6}{H_5}\overline C H{}_2C6​H5​CH2​>(CH3)2C‾H{(C{H_3})_2}\overline C H(CH3​)2​CH>(CH3)3C‾{(C{H_3})_3}\overline C(CH3​)3​C
  3. C
    (CH3)3C‾{(C{H_3})_3}\overline C(CH3​)3​C>(CH3)2C‾H{(C{H_3})_2}\overline C H(CH3​)2​CH>C6H5C‾H2{C_6}{H_5}\overline C H{}_2C6​H5​CH2​>C‾Cl3\overline C C{l_3}CCl3​
  4. D
    C6H5C‾H2{C_6}{H_5}\overline C H{}_2C6​H5​CH2​>C‾Cl3\overline C C{l_3}CCl3​>(CH3)3C‾{(C{H_3})_3}\overline C(CH3​)3​C>(CH3)2C‾H{(C{H_3})_2}\overline C H(CH3​)2​CH
View written solutionFree

Correct answer: B

  1. Identify the given carbanions

We need the decreasing order of stability of:

  • (CH3)3C‾ (CH_3)_3\overline{C}(CH3​)3​C : tert-butyl carbanion
  • C‾Cl3 \overline{C}Cl_3CCl3​ : trichloromethyl carbanion
  • (CH3)2C‾H (CH_3)_2\overline{C}H(CH3​)2​CH : isopropyl carbanion
  • C6H5C‾H2 C_6H_5\overline{C}H_2C6​H5​CH2​ : benzyl carbanion

  1. General factors affecting carbanion stability

A carbanion is stabilized by:

  • Electron-withdrawing groups through −I-I−I effect
  • Resonance delocalization of negative charge
  • Less alkyl substitution, because alkyl groups show +I+I+I effect and destabilize carbanions

So:

  • More alkyl groups ⇒\Rightarrow⇒ less stable carbanion
  • Resonance stabilization greatly increases stability
  • Strong −I-I−I groups like ClClCl also stabilize strongly

  1. Compare each species

(i) C‾Cl3\overline{C}Cl_3CCl3​

The three chlorine atoms exert a very strong −I-I−I effect, pulling electron density away from the negatively charged carbon. This strongly stabilizes the carbanion.

So this is highly stable.

(ii) C6H5C‾H2C_6H_5\overline{C}H_2C6​H5​CH2​

This is a benzyl carbanion. The negative charge is delocalized into the benzene ring by resonance:

C6H5−CH2−↔resonance forms in the ringC_6H_5-CH_2^- \leftrightarrow \text{resonance forms in the ring}C6​H5​−CH2−​↔resonance forms in the ring

Hence it is also strongly stabilized.

Between benzyl and CCl3−CCl_3^-CCl3−​, the strong stabilization by three chlorine atoms makes C‾Cl3\overline{C}Cl_3CCl3​ more stable in standard JEE ordering.

Thus:

C‾Cl3>C6H5C‾H2\overline{C}Cl_3 > C_6H_5\overline{C}H_2CCl3​>C6​H5​CH2​

(iii) (CH3)2C‾H(CH_3)_2\overline{C}H(CH3​)2​CH

This is a secondary carbanion. Two methyl groups show +I+I+I effect, which push electron density toward the negatively charged carbon and destabilize it.

(iv) (CH3)3C‾(CH_3)_3\overline{C}(CH3​)3​C

This is a tertiary carbanion. Three methyl groups exert even stronger +I+I+I effect, so it is the least stable.

Therefore:

(CH3)2C‾H>(CH3)3C‾(CH_3)_2\overline{C}H > (CH_3)_3\overline{C}(CH3​)2​CH>(CH3​)3​C
  1. Combine all comparisons

The decreasing stability order is:

C‾Cl3>C6H5C‾H2>(CH3)2C‾H>(CH3)3C‾\overline{C}Cl_3 > C_6H_5\overline{C}H_2 > (CH_3)_2\overline{C}H > (CH_3)_3\overline{C}CCl3​>C6​H5​CH2​>(CH3​)2​CH>(CH3​)3​C
  1. Match with options

This matches Option B.


  1. Comparison with stored correct answer

Stored correct answer: B

Our derived answer: B

So the answer agrees with the stored correct answer.

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