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Handout-Aromatic Compound 1

Electrophilic aromatic substitution is an important reaction type for aromatic compounds. The mechanism involves an electrophile attacking the aromatic ring, with activation occurring through electron-donating substituents and deactivation through electron-withdrawing groups. Substituents can also direct reaction to the ortho/para or meta positions. Aromatic compounds undergo halogenation, nitration, sulfonation, Friedel-Crafts alkylation/acylation, and nucleophilic aromatic substitution.

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Wira Oktafine Reppi , M.Si (BrilliantClass)
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113 views

Handout-Aromatic Compound 1

Electrophilic aromatic substitution is an important reaction type for aromatic compounds. The mechanism involves an electrophile attacking the aromatic ring, with activation occurring through electron-donating substituents and deactivation through electron-withdrawing groups. Substituents can also direct reaction to the ortho/para or meta positions. Aromatic compounds undergo halogenation, nitration, sulfonation, Friedel-Crafts alkylation/acylation, and nucleophilic aromatic substitution.

Uploaded by

Wira Oktafine Reppi , M.Si (BrilliantClass)
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Wirareppi@gmail.

com AROMATIC COMPOUNDS ORGANIC CHEMISTRY

Electrophilic Aromatic Substitution


 Arene (Ar-H) is the
generic term for an
aromatic hydrocarbon
 The aryl group (Ar) is
derived by removal of a
hydrogen atom from an
arene
 Aromatic compounds
undergo electrophilic
aromatic substitution
(EAS): The electrophile
has a full or partial
positive charge

Mechanism reaction:

 Halogenation of Benzene

 Iodine is so unreactive that an alternative method must be used

 Nitration of Benzene
Nitration of benzene occurs with a mixture of concentrated nitric and sulfuric acids
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 Sulfonation of Benzene
Sulfonation
occurs most
rapidly using
fuming sulfuric
acid
(concentrated
sulfuric acid
that contains
SO3)

 Friedel-Crafts Alkylation
An aromatic ring can be
alkylated by an alkyl halide
in the presence of a Lewis
acid

 Friedel-Crafts Acylation

 Problems associated with Friedel–Crafts alkylation can be avoided by conducting an acylation


followed by a reduction of the carbonyl group (Clemmensen or wolf-Kishner reduction) to a
methylene group (CH2):

Effects of Substituents on Reactivity and Orientation


 Activating groups cause the aromatic ring to be more reactive than benzene
 Deactivating groups cause the aromatic ring to be less reactive than benzene
 Ortho-para directors direct future substitution to the ortho and para positions
 Meta directors direct future substitution to the meta position
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Classification of Substitutents :

The methyl group of toluene is an ortho-para directo:

Strong electron-withdrawing groups such as nitro, carboxyl, and sulfonate are deactivators and meta
directors:

 Reactions of the Side Chain of Alkylbenzenes


Benzylic Radicals and Cations
When toluene undergoes hydrogen abstraction from its methyl group it produces a benzyl
radical

 Additions to the Double Bond of Alkenylbenzenes


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Oxidation of the Side Chain

Nucleophilic Aromatic Substitution


A nucleophile replaces a leaving group
on the aromatic ring.
Electron-withdrawing substituents
activate the ring for nucleophilic
substitution.
Mechanism:

Benzyne Mechanism

Mechanism:
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Soal:
1. Provide a mechanism that accounts for the following result
a. b.

2. Starting with benzene and the appropriate acyl chloride or acid anhydride, outline a syn-thesis of
each of the following:

(e)

3. Provide a mechanism that accounts for the following result


a. b.

4. Suppose you needed to synthesize m-chloroethylbenzene from benzene


a. b.

5. Provide a detailed mechanism for each of the following reactions

6. Write mechanisms that account for the products of the following reactions:

7. Predict the major products of the following reactions:

8. Show how you might synthesize each of the following compounds starting with either benzyl
bromide or allyl bromide:
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9. 2-Methylnaphthalene can be synthesized from toluene through the following sequence of reactions.
Write the structure of each intermediate.

10. Deduce the structures of compounds E–L in the roadmap below.

11.

12. A

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