Why is it difficult to stop the reaction at the mono-brominated stage? OHBrominating of Phenols3Br₂BrOHBrBr

Answered: Brominating of Phenols

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Why is it difficult to stop the reaction at the mono-brominated stage?

OH
Brominating of Phenols
3Br₂
Br
OH
Br
Br

Expert Solution

Step 1: Aromatic Electrophilic substitution reactions

EAS reactions are a class of reactions in which an electrophile (an electron-deficient species) replaces one of the hydrogen atoms on an aromatic ring. The following reasons primarily make aromatic compounds' electrophilic substitution reaction more favorable

The electron-rich pi system: Aromatic compounds, like benzene, have a delocalized pi-electron system formed by the p-orbitals of the carbon atoms in the ring. This system contains a total of 6 pi electrons (3 double bonds or 6 pi electrons in benzene), which is ideal for stability due to Huckel's rule, making the aromatic ring highly stable and resistant to addition reactions.
Activation of the ring: The presence of the pi electrons in the aromatic ring activates it towards electrophilic attacks. Electrophiles are attracted to the electron-rich regions of the ring, typically leading to the substitution of a hydrogen atom with the electrophile.

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