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.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter9: Addition Via Cyclic Intermediate
Section: Chapter Questions
Problem 9CTQ
icon
Related questions
icon
Concept explainers
Question
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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning