Stability orders of intermediates
General Organic Chemistry (GOC) · Chemistry
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Rank: CH₃⁺, (CH₃)₂CH⁺, PhCH₂⁺, Ph₃C⁺ by stability. Step 1: CH₃⁺: no donors — least stable. Step 2: (CH₃)₂CH⁺: 6 α-H hyperconjugation — better. Step 3: PhCH₂⁺: benzyl resonance delocalizes charge into ring — better still. Step 4: Ph₃C⁺: three rings share the charge — most stable (isolable as salt!). Order: Ph₃C⁺ > PhCH₂⁺ > (CH₃)₂CH⁺ > CH₃⁺.