CH223HW1solutions

CH223HW1solutions - CH 223-001/003 Spring 2012 Homework 1...

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CH 223-001/003 Spring 2012 Homework 1 SOLUTIONS 1. Please provide a detailed arrow-pushing mechanism for the bromination of benzene with Br 2 and FeBr 3 . Include all relevant resonance structures. You may abbreviate the electrophile as “Br + .” This comes straight from lecture notes and/or your textbook. 2. Please rank the following aromatic compounds in order of their reactivity in electrophilic aromatic substitution: anisole, nitrobenzene, acetophenone, toluene, benzene. Briefly explain your answer. This comes straight from lecture notes and/or your textbook. 3. The nitration of toluene gives o- and p-nitrotoluene as the major products. Please explain this observation, using structures (rather than words) as much as possible. This comes straight from lecture notes and/or your textbook. 4. (This may be challenging – try it anyhow.) Please construct a potential energy diagram for the electrophilic aromatic substitution of benzene with an electrophile, E + . Your diagram should include benzene, the cationic intermediate,
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This note was uploaded on 03/03/2012 for the course CHEM 223 taught by Professor S during the Fall '10 term at N.C. State.

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CH223HW1solutions - CH 223-001/003 Spring 2012 Homework 1...

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