Question
Which is more stable and why?
  1. $\text{C}_6\text{H}_5-\stackrel{\oplus\ \ \ \ }{\text{CH}_2}\text{ or }\text{C}_6\text{H}_{11}\stackrel{\oplus\ \ \ \ }{\text{CH}_2}$
  2. $(\text{C}_6\text{H}_5)\stackrel{\bf.\ \ \ }{\text{CH}}\text{ or }\text{C}_6\text{H}_5\stackrel{\bf.\ \ \ \ \ }{\text{CH}_2}$
  3. $(\text{C}_6\text{H}_5)\stackrel{\bf.\ \ \ }{\text{CH}}_2\text{ or }\text{CH}_2=\text{CH}-\stackrel{\bf.\ \ \ \ \ }{\text{CH}_2}$

Answer

  1. $\text{C}_6\text{H}_5\stackrel{\oplus\ \ \ \ }{\text{CH}_2}$ is more stable due to resonance (5 resonating structures).
  2. $(C_6H_5)CH$ is more stable due to more resonating structures.
  3. $C_6H_5CH_2$ is more stable due to 5 resonating structures whereas $CH_2=CH-CH_2$​​​​​​​ has two resonating structures.

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