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

4:51 minutes

Problem 39b

Textbook Question

b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.
chlorobenzene, 1-chloro-2,4-dinitrobenzene, p-chloronitrobenzene

Verified step by step guidance

Identify the compounds provided in the problem and determine the substituents attached to the aromatic ring. Substituents can either activate or deactivate the ring toward electrophilic aromatic substitution (EAS). Activating groups increase the tendency for EAS, while deactivating groups decrease it.

Classify each substituent as either an electron-donating group (EDG) or an electron-withdrawing group (EWG). EDGs, such as -OH, -OCH3, and alkyl groups, stabilize the intermediate carbocation formed during EAS, making the reaction more favorable. EWGs, such as -NO2, -CF3, and -COOH, destabilize the intermediate carbocation, making the reaction less favorable.

Consider the resonance and inductive effects of each substituent. Resonance effects occur when the substituent can donate or withdraw electrons through π-bond interactions, while inductive effects involve electron withdrawal or donation through σ-bonds. Substituents with strong resonance-donating effects (e.g., -OH, -NH2) are typically stronger activators than those with only inductive effects.

Rank the compounds based on the overall activating or deactivating influence of their substituents. Compounds with strong activating groups will have the greatest tendency to undergo EAS, while those with strong deactivating groups will have the least tendency.

If multiple substituents are present on a single aromatic ring, evaluate their combined effects. Activating groups generally dominate over deactivating groups, but the position of the substituents (ortho, meta, or para) can also influence the reactivity. Use this information to finalize the ranking of the compounds.

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 (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This reaction is crucial for modifying aromatic compounds and is influenced by the nature of substituents already present on the ring, which can either activate or deactivate the ring towards further substitution.

Activating and Deactivating Groups

Substituents on an aromatic ring can be classified as activating or deactivating based on their electronic effects. Activating groups, such as -OH or -NH2, increase the electron density of the ring, making it more reactive towards electrophiles. In contrast, deactivating groups, like -NO2 or -CF3, withdraw electron density, reducing the ring's reactivity and influencing the position of substitution.

Ortho/Para vs. Meta Directing

The position of substitution in electrophilic aromatic substitution is also determined by whether the substituents are ortho/para or meta directing. Activating groups typically direct incoming electrophiles to the ortho and para positions, while deactivating groups usually direct them to the meta position. Understanding these directing effects is essential for predicting the outcome of EAS reactions.

Watch next

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

Start learning

Related Videos

Related Practice

Textbook Question

Predict the major products of the following reactions.

(a) 2,4-dinitrochlorobenzene + NaOCH₃

Textbook Question

Predict the major products of the following reactions.

Textbook Question

In Chapter 23, we learned about the electrophilic aromatic nitration reaction. When phenol is subjected to these conditions with a large excess of nitric acid, a molecule called picric acid is produced. Predict the product of this reaction and explain why the pK_a value of this compound is 0.38.

Textbook Question

Predict the major products of the following reactions.

(b) phenol + tert-butyl chloride + AlCl₃

Textbook Question

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole

Textbook Question

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

Textbook Question

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.