Vollhardt 6th Ed. (2010)
CH 16: Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Solutions can be seen at mendelset.com/chapters/1146


  1. Problem # 588

    Let's draw resonance forms to see why some groups are EDG or EWG. (I've started you off)

    Where are the positive or negative charges placed in EDG/EWG? (ortho/meta/para) Why would this affect EAS reactions?

    Note: EDG = electron donating group, EWG = electron withdrawing group

  2. Problem # 589

     -OR is an EDG and an ortho-para director. Let's draw an EAS reaction's cyclohexadienyl cation intermediates to demonstrate why this is true. I've started you off.

    What's good about ortho/para? What's bad about meta?

  3. Problem # 590

    -NO2 is an EWG and a meta director. Let's draw an EAS reaction's cyclohexadienyl cation intermediates to demonstrate why this is true. I've started you off.

    What's good about meta? What's bad about ortho/para?

  4. Problem # 592

    Naphthalene undergoes eletrophilic substitution at C-1.

    Why is this the case, even though substitution at C-2 gives more resonance forms?