Consider the structure of nitrosobenzene: N O (a) Draw the resonance structures of the

Chapter 19, Problem 19.64

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Consider the structure of nitrosobenzene: N O (a) Draw the resonance structures of the sigma complex formed when nitrosobenzene reacts with an electrophile (E+) at the ortho position. (b) Draw the resonance structures of the sigma complex formed when nitrosobenzene reacts with an electrophile (E+) at the meta position. (c) Draw the resonance structures of the sigma complex formed when nitrosobenzene reacts with an electrophile (E+) at the para position. (d) Compare the stability of the intermediates from parts ac of this problem and then predict whether the nitroso group is ortho-para directing or meta directing. (e) The nitroso group has a lone pair adjacent to the ring (suggesting that it could be an activator), yet it also has a p bond to a heteroatom in conjugation with the ring (suggesting that it could be a deactivator). Experiments reveal that this group is a deactivator. Based on this information, identify which of the following groups is expected to have properties most similar to the nitroso group and explain your choice: OH NO2 CH3 Cl