Organic Chemistry II,

Electrophilic Aromatic Substitution (EAS) Homework II

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CH₃ CH₃

HA

1. Provide a complete mechanism for the above Electrophilic Aromatic Substitution Reaction. Pay close attention to details, including lone pairs, formal charges and the use of curved arrows.
2. Why is the methyl group in toluene an ortho/para director? Explain, using drawings to support your answer. Compare the stabilities of the competing intermediates (add E⁺ ortho, meta, para and compare).