What is the correct order of decreasing stability of the following cations?
$I - C H_{3} - * C H - C H_{3}$
$I I - C H_{3} - * C H - O C H_{3}$
$I I I - C H_{3} - * C H - C H_{2} - O C H_{3}$

I I > I > I I I

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I I > I I I > I

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I I I > I > I I

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I > I I > I I I

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Solution

The correct option is A $I I > I > I I I$
$C H_{3} - * C H - C H_{3} \to$ Stable due to +I effect of 2 $- C H_{3}$ groups.
$C H_{3} - * C H - O C H_{3} \to$ Stable due to strong +R effect of $- O C H_{3}$ group (lone pair- $σ$ bond-positive charge).
$C H_{3} - * C H - C H_{2} - O C H_{3} \to$ Destabilised by -I effect of $- O C H_{3}$ group.
$\Rightarrow$ R effect in $I I$ dominates I effect in $I$
Hence, the correct order of stability is $I I > I > I I I$ .

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C H_{2} - + C H - C H_{3}

C H_{3} - + C H - O C H_{3}

C H_{3} - + C H - C O C H_{3}

{C H}_{3} - C H = {C H}_{2}

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{C H}_{3} - C_{3} = C H - {C H}_{3}

{C H}_{3} - {C H}_{3} | C = {C H}_{3} | C - {C H}_{3}

(i) C H_{3} - + C H - C H_{2} - O C H_{3}

(i i) C H_{3} - + C H - C H_{2} - C H_{3}

(i i i) C H_{3} - + C H - O | | C - C H_{3}

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$| C H_{3} - \oplus C H - C H_{3} | | C H_{3} - \oplus C H - O C H_{3} | | | C H_{3} - \oplus C H - C O C H_{3}$

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