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3. Are the following substituents ortho/para or meta directors? EXPLAIN WHY. a. CF3 b. NO2


3. Are the following substituents ortho/para or meta directors? EXPLAIN WHY.

a. CF3


b. NO2

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Answer #1

Meta Directors: all substituents that withdraw electrons by resonance and/or inductive effects (EXCEPT halogens, which donate electrons by resonance, but withdraw electrons inductively) Common Meta Directors • --NO2 • --CF3

• --+NR3

• --C_N   

Why are electron withdrawing groups meta directors? If you have a substituent, which removes electron density from the benzene ring, you want to make the most stable carbocation possible. Compare the relative stability of resonance contributors for carbocations with a strongly electron withdrawing substituent like nitro (NO2):

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