Problem 1: Draw the mechanism for the nitration of methyl benzoate as shown in the figure. Indicate all the possible resonance structures for the obtained cation intermediate that is formed after the ring attacks the nitronium electrophile. Label (use a number below it) the resonance structures of the cation intermediate. OCH3 + HONO, H,SO, OCH3 + H20 NO2 Methyl benzoate Methyl m-nitrobenzoate • Draw the mechanism for the ortho-nitration of methyl benzoate which rarely happens. Indicate all the possible resonance structures for the obtained cation intermediate that is formed after the ring attacks the nitronium electrophile. Label (use a letter below it) the resonance structures of the cation intermediate. • Why is the meta product favored? Explain by using the labeled intermediates for reasoning.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Problem 1:
Draw the mechanism for the nitration of methyl benzoate as shown in the figure. Indicate all the
possible resonance structures for the obtained cation intermediate that is formed after the ring
attacks the nitronium electrophile. Label (use a number below it) the resonance structures of the
cation intermediate.
`OCH3 + HONO2
H,SO,
OCH3 + H2O
NO2
Methyl benzoate
Methyl m-nitrobenzoate
Draw the mechanism for the ortho-nitration of methyl benzoate which rarely happens. Indicate
all the possible resonance structures for the obtained cation intermediate that is formed after the
ring attacks the nitronium electrophile. Label (use a letter below it) the resonance structures of
the cation intermediate.
Why is the meta product favored? Explain by using the labeled intermediates for reasoning.
Transcribed Image Text:Problem 1: Draw the mechanism for the nitration of methyl benzoate as shown in the figure. Indicate all the possible resonance structures for the obtained cation intermediate that is formed after the ring attacks the nitronium electrophile. Label (use a number below it) the resonance structures of the cation intermediate. `OCH3 + HONO2 H,SO, OCH3 + H2O NO2 Methyl benzoate Methyl m-nitrobenzoate Draw the mechanism for the ortho-nitration of methyl benzoate which rarely happens. Indicate all the possible resonance structures for the obtained cation intermediate that is formed after the ring attacks the nitronium electrophile. Label (use a letter below it) the resonance structures of the cation intermediate. Why is the meta product favored? Explain by using the labeled intermediates for reasoning.
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