Question

Aromatic substitution reactions occur by addition of an electrophile such as $\mathrm{Br}^{+}$ to the aromatic ring to yield an allylic carbocation intermediate, followed by loss of $\mathrm{H}^{+}$. Show the structure of the intermediate formed by reaction of benzene with $\mathrm{Br}^{+}$

Name: Problem 49, Chapter 15: Organic Chemistry
Uploaded: 2020-05-28T17:56:33-08:00
Duration: 1 min 57 s
Channel: Mercedes Mazza
Description: Aromatic substitution reactions occur by addition of an electrophile such as Br^+ to the aromatic ring to yield an allylic carbocation intermediate, followed by loss of H^+. Show the structure of the intermediate formed by reaction of benzene with Br^+

   Aromatic substitution reactions occur by addition of an electrophile such as $\mathrm{Br}^{+}$ to the aromatic ring to yield an allylic carbocation intermediate, followed by loss of $\mathrm{H}^{+}$. Show the structure of the intermediate formed by reaction of benzene with $\mathrm{Br}^{+}$

Organic Chemistry

John McMurry 8th Edition

Chapter 15, Problem 49

Instant Answer

Solved by Expert Mercedes Mazza

05/28/2020

Step 1

The benzene ring is represented as follows: \[ \begin{array}{c} \chemfig{**6(------)} \end{array} \] and the electrophile $\mathrm{Br}^{+}$ is represented as $\mathrm{Br}^{+}$. Show more…

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Aromatic substitution reactions occur by addition of an electrophile such as $\mathrm{Br}^{+}$ to the aromatic ring to yield an allylic carbocation intermediate, followed by loss of $\mathrm{H}^{+}$. Show the structure of the intermediate formed by reaction of benzene with $\mathrm{Br}^{+}$

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Key Concepts

Electrophilic Aromatic Substitution

This is the general reaction mechanism in which an electrophile attacks an aromatic ring, temporarily disrupting its aromaticity by forming a sigma complex, before the loss of a proton restores full aromatic stabilization.

Arenium Ion (Sigma Complex)

This intermediate, formed when the electrophile bonds to the benzene ring, is a resonance-stabilized carbocation that, despite the loss of aromaticity, is stabilized by delocalization of the positive charge over several carbon atoms in the ring.

Resonance Stabilization

The stability of the arenium ion comes from resonance, which allows the positive charge generated by electrophilic attack to be distributed across multiple atoms in the aromatic ring, reducing the energy of the intermediate.

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