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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

Question: Predict the major products of the following reactions:

(a) Nitration of bromobenzene

(b) Bromination of nitrobenzene

(c) Chlorination of phenol

(d) Bromination of aniline

Question:Predict the major product(s) of the following reactions:

(a)

(b)

(c)

(d)

Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of AlCl3. Propose a mechanism for the reaction.

Starting with either benzene or toluene, how would you synthesize the

following substances? Assume that ortho and para isomers can be

separated.

(a) 2-Bromo-4-nitrotoluene (b) 1,3,5-Trinitrobenzene

(c)2,4,6-Tribromoaniline (d)m-Fluorobenzoic acid

Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.
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