Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Which of following reacts slower than benzene in electrophilic substitution? (1) C6H5CH3 (2) C6H5NO2 (3) C6H5OH (4) C6H5NH2

Short Answer

Expert verified
(2) C6H5NO2

Step by step solution

01

Understanding electrophilic substitution

Electrophilic substitution involves an electrophile attacking a benzene ring. The rate of this reaction depends on the substituents attached to the benzene ring.
02

Identifying electron-donating and electron-withdrawing groups

Electron-donating groups (EDGs) increase the electron density on the benzene ring and enhance its reactivity towards electrophiles. Electron-withdrawing groups (EWGs) decrease the electron density on the benzene ring and decrease its reactivity towards electrophiles.
03

Analyzing the substituents

Consider the listed substituents of each compound: 1. C6H5CH3 has a methyl group (EDG). 2. C6H5NO2 has a nitro group (EWG). 3. C6H5OH has a hydroxyl group (EDG). 4. C6H5NH2 has an amino group (EDG).
04

Conclusion

The nitro group is an electron-withdrawing group that decreases the reactivity of benzene towards electrophilic substitution. Hence, C6H5NO2 (option 2) reacts slower than benzene in electrophilic substitution.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Electron Donating Groups (EDGs)
Electron donating groups (EDGs) are substituents that increase the electron density on a benzene ring. They do this by either through electron-releasing inductive effects or by resonance effects, which stabilizes the benzene ring and enhances its reactivity towards electrophiles. For example, in compound C6H5CH3, the methyl group is an EDG. This group donates electrons through an inductive effect, making the benzene more reactive. Similarly, the hydroxyl group (as in C6H5OH) and the amino group (as in C6H5NH2) donate electrons by resonance, further increasing reactivity. Electrophilic substitution reactions with benzene derivatives containing EDGs are often faster than with benzene itself.
Electron Withdrawing Groups (EWGs)
Electron withdrawing groups (EWGs) are substituents that reduce the electron density on a benzene ring. They achieve this by either withdrawing electrons through electronegativity or through resonance effects. This makes the benzene ring less reactive towards electrophiles. For instance, in compound C6H5NO2, the nitro group is a strong EWG. It withdraws electron density through both inductive effects and resonance, leading to a decrease in the reactivity of the benzene ring. Thus, electrophilic substitution reactions involving benzene derivatives with EWGs occur slower than with benzene itself.
Benzene Derivatives Reaction Rates
The rate at which benzene derivatives undergo electrophilic substitution is influenced by the type of substituent present on the benzene ring. Electron donating groups (EDGs) enhance the reaction rate, while electron withdrawing groups (EWGs) slow it down. For examples:
  • Compounds like C6H5CH3 (with a methyl group) react faster than benzene due to the electron-donating nature of the methyl group.
  • Compounds like C6H5NO2 (with a nitro group) react slower than benzene because the nitro group is a strong EWG.
  • Hydroxyl and amino groups, as seen in C6H5OH and C6H5NH2 respectively, also increase the reactivity due to their electron-donating effects.
Understanding whether a substituent is an EDG or EWG helps predict the reactivity of benzene derivatives in electrophilic substitution reactions.

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free