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Chapter 16: Q2P (page 486)

Propose a mechanism for the electrophilic fluorination of benzene withF-TEDA-BF4.

Short Answer

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Formation of fluorobenzene

Step by step solution

01

Electrophilic substitution

In electrophilic aromatic substitution reactions, the hydrogen atom present in the aromatic ring is replaced by an electrophile.

The pi-electron of benzene attacks the fluorine ofF-TEDA-BF4and the non-aromatic intermediates losses 鈥� H to give the fluorinated product.

02

Mechanism

The mechanism begins with the aromatic ring attacking the fluorine atom bound to nitrogen in F-TEDA-BF4. This is because this fluorine is the most electrophilic atom. With this attack, we generate structure 2 which upon reacting with base rearomatizes to give the final product, fluorobenzene. The mechanism is as follows:

Formation of fluorobenzene

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Most popular questions from this chapter

At what position, and on what ring, would you expect the followingsubstances to undergo electrophilic substitution?

(a)

(b)

(c)

(d)

Use your knowledge of directing effects, along with the following data, to deduce the directions of the dipole moments in aniline andbromobenzene.

Question: When benzene is treated with D2SO4, deuterium slowly replaces all six hydrogens in the aromatic ring. Explain.

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