Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

Previous problemNext problem

2:15 minutes

Problem 12d

Textbook Question

Predict the mononitration products of the following compounds.
d. p-methoxybenzoic acid

Verified step by step guidance

Identify the functional groups present in the compound. p-Methoxybenzoic acid contains a methoxy group (-OCH₃) and a carboxylic acid group (-COOH) attached to a benzene ring. The methoxy group is an electron-donating group (activating), while the carboxylic acid group is an electron-withdrawing group (deactivating).

Determine the directing effects of the substituents. The methoxy group is an ortho/para-directing group, meaning it directs incoming electrophiles to the ortho and para positions relative to itself. The carboxylic acid group is a meta-directing group, meaning it directs incoming electrophiles to the meta position relative to itself.

Analyze the combined effects of the substituents. Since the methoxy group is para to the carboxylic acid group, the positions influenced by each substituent will overlap. The methoxy group will strongly activate the para position relative to itself (which is also the meta position relative to the carboxylic acid group).

Consider the reaction conditions. Mononitration involves the introduction of a nitro group (-NO₂) to the benzene ring using a nitrating mixture (HNO₃ and H₂SO₄). The nitro group will preferentially add to the most activated position, which is the para position relative to the methoxy group.

Predict the product. The nitro group will be added to the para position relative to the methoxy group, resulting in 4-methoxy-3-nitrobenzoic acid as the mononitration product.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for understanding how substituents on the ring influence the reactivity and orientation of further substitutions, such as nitration.

Activating and Deactivating Groups

Substituents on an aromatic ring can either activate or deactivate the ring towards electrophilic substitution. Activating groups, like methoxy (-OCH3), increase electron density and direct incoming electrophiles to ortho and para positions, while deactivating groups reduce reactivity and typically direct electrophiles to the meta position.

Nitration Reaction

Nitration is a specific type of electrophilic aromatic substitution where a nitro group (-NO2) is introduced into an aromatic compound. The reaction typically involves the use of a nitrating mixture, such as concentrated nitric acid and sulfuric acid, and the position of nitration is influenced by the nature of existing substituents on the aromatic ring.

Watch next

Master Activity and Directing Effects with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

A mixture of 0.10 mol benzene and 0.10 mol p-xylene was allowed to react with 0.10 mol nitronium ion until all the nitronium ion was gone. Two products were obtained: 0.002 mol of one and 0.098 mol of the other.

b. Why was more of one product obtained than of the other?

Textbook Question

Indigo is a dye that was originally isolated from coal tar. In 1905, Johann Friedrich Wilhelm Adolf von Baeyer won a Nobel Prize for a method that allowed indigo to be isolated from plants [a green chemist ahead of his time.] If you nitrated indigo using the reaction learned in this chapter, at which carbon would you expect the nitro group to attach?

Textbook Question

Substitution at the benzylic position of the molecules shown was observed to occur at different rates. Explain this observation.

Textbook Question

Which of the following phenoxides should be a stronger nucleophile?

Textbook Question

Predict the mononitration products of the following compounds.

e. m-cresol (m-methylphenol)

Textbook Question

Predict the mononitration products of the following compounds.

f. o-hydroxyacetophenone

Textbook Question

Are the following substituents ortho–para directors or meta directors?