8. Compare the reactivity of methyl benzoate and phenol under bromination conditions. Classify each as an activating or deactivating group and explain your reasoning. Hint: draw out the complete structure of each showing all lone pairs. 9. Show all the resonance structures for methyl benzoate. Using these resonance structures, explain whether the substituent is an ortho, para directing group or meta directing group.

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8. Compare the reactivity of methyl benzoate and phenol under bromination conditions. Classify each as
an activating or deactivating group and explain your reasoning. Hint: draw out the complete structure of
each showing all lone pairs.
9. Show all the resonance structures for methyl benzoate. Using these resonance structures, explain
whether the substituent is an ortho, para directing group or meta directing group.
10. Using acetanilide, which is an activating group, show the mechanism for para addition. Include all
resonance structures. Explain why para addition, like ortho addition, is favored when an activating group
is on the ring.
11. Based on your knowledge of reactivity of substituted aromatic compounds, what do you hypothesize
will be the major product of the competitive nitration reaction (methyl benzoate)?
Transcribed Image Text:8. Compare the reactivity of methyl benzoate and phenol under bromination conditions. Classify each as an activating or deactivating group and explain your reasoning. Hint: draw out the complete structure of each showing all lone pairs. 9. Show all the resonance structures for methyl benzoate. Using these resonance structures, explain whether the substituent is an ortho, para directing group or meta directing group. 10. Using acetanilide, which is an activating group, show the mechanism for para addition. Include all resonance structures. Explain why para addition, like ortho addition, is favored when an activating group is on the ring. 11. Based on your knowledge of reactivity of substituted aromatic compounds, what do you hypothesize will be the major product of the competitive nitration reaction (methyl benzoate)?
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