Question

For pyridine.....

(a) Show each potential intermediate that can be generated when an electrophile adds to pyridine. Use a generic E for the electrophile.

(b) Draw all the resonance structures for each potential intermediate

(c) State whether the most stable intermediate occurs for ortho, meta or para substitution. Provide an argument (15 words or less).

(d) You are going to start with benzene, and proceed through molecule A on your way to molecule B. Use the NMR/IR spectra to solve for molecule A and B. Next show the synthetic route to get to molecule B.

Molecule A:C13H180 100 50 way D 4 DOO 5000 2000 1500 1000 sbo NAVENUHBERI- ЗН ЗН ЗН 4H 2H IH 2H HA 8 7 6 5 2 0 PPM Molecule B

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