Answered: Propose steps for the following…

Propose steps for the following conversions using a reaction of a diazonium salt in at least one step of each conversion. Q.) Toluene to 4-fluorobenzoic acid

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter17: Carboxylic Acids

Section: Chapter Questions

Problem 17.23P

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Propose steps for the following conversions using a reaction of a diazonium salt in at least one step of each conversion.

Q.) Toluene to 4-fluorobenzoic acid

Expert Solution

Step 1

Here we have to prepare 4-fluorobenzoic acid from toluene, this conversion including the following steps:

Nitration.
Reduction.
Diazotisation.
Oxidation.

Step 2

$\to_{N i t r a t i o n}^{H N O_{3} / H_{2} S O_{4}}$ $\to_{R e d u c t i o n}^{[H]}$

(Toluene) (4-nitrotoluene) (4-methylnitroaniline)

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