DISCUSSION 4 ORGANIC 2

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Your Name: 1. Determine if each compound below is aromatic, anti-aromatic, or neither (only one option per structure). Then, discuss why you believe this option to be true for each case.

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2. (a) Starting from benzene, propose a viable synthesis for the para-product below. For each step, show all necessary reagents/conditions and draw the major product expected after each step in your proposed synthesis.

(b) Discuss why minimal ortho product is observed in this synthesis.

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(c) Show how you could modify your synthetic proposal so that the ortho product formed below is the only product observed. You can fill in the missing reagents in the correct step order above or below the arrow. (Hint: Sulfonation is a reversible reaction).

(d) Discuss how 1H NMR would allow a synthetic chemist to differentiate between the ortho and para products shown above. Be specific. Your discussions should talk about number of signals expected, splitting patterns, integrations and important chemical shift regions that would be significant in differentiating these two constitutional isomers.