Benzyl cation template

PhCH₂⁺: the cation on CH₂, then on the two ortho carbons and the para carbon, each form reached by moving one ring π bond.

What the template shows

• The ring π electrons spread the positive charge onto the ortho and para carbons
• Resonance contributors
• Positive charge: CH₂, ortho, para, ortho′
• Four contributors: the charge is shared by the benzylic carbon and the ortho and para ring carbons, never the meta carbons.
• The benzyl cation is about as stable as a secondary alkyl cation, so benzylic halides react readily by SN1.
• The benzyl radical and anion are delocalised onto the same carbons.
• Contributors are not in equilibrium: the real species is one hybrid of them · every part of this figure is editable

Drawn with 28 atoms, 6 arrows, 2 shapes – every one editable in MolDraw.

Sources

• Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 7 Textbook
• Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020 Textbook