Organic Chemistry Reactions

Reactivity of Polynuclear Aromatic Hydrocarbons

• Larger polynuclear aromatic hydrocarbons are less reactive than anthracene and phenanthrene.

Sulfonation in the Chemical Industry

• The primary economic significance of sulfonation is the manufacture of dyes and pigments.
• Sulfonation of an alkylbenzene produces an alkylbenzene sulfonic acid.
• The role of the base in the neutralization process is to neutralize the sulfonic acid to form a salt.
• The resulting product after neutralizing the alkylbenzenesulfonic acid with a base is an alkylbenzene sulfonate.

Electrophilic Aromatic Substitution Reactions

• Toluene is more reactive than benzene in electrophilic aromatic substitution reactions due to activation.
• The primary product of the nitration of toluene is a mixture of ortho and para-substituted products.

Friedel-Crafts Alkylation Reaction

• Aluminum chloride is a commonly used catalyst in the Friedel-Crafts alkylation reaction.
• The role of the Lewis acid catalyst is to initiate the reaction.
• Friedel-Crafts alkylation is a reaction between alkyl halides and benzene in the presence of Lewis acid catalysts.

Chemical Reactions

• Friedel-Crafts acylation is a reaction between acyl halides and benzene in the presence of Lewis acid catalysts.
• Clemmensen reduction is a reaction that reduces ketones to alkanes using zinc-mercury amalgam.
• Oxidation reaction of phenol produces quinone.

Directing Effects of Substituents on Benzene

• Meta-directing functional groups include -NO2 and -COX.
• Ortho, para-directing functional groups include -OH, -NH2, -X, and -OCH3.

Aromatic Compounds

• August Kekulé proposed in 1872 that the structure of benzene is a ring of six sp2 hybrid carbon atoms.
• The C-C bonds in benzene are described as something in between single and double bonds.
• The bond angle in benzene is 120°.
• The carbon-carbon bond lengths in benzene are unique because they are equal in length.
• Benzene contains three conjugated double bonds.

Reaction of Benzene with Bromine

• When bromine is added to benzene, no reaction occurs, and the red bromine color remains.
• The reaction between bromine and benzene is a substitution reaction.
• The addition of a catalyst like ferric bromide speeds up the substitution reaction.
• The result of the reaction between bromine, benzene, and a catalyst like ferric bromide is the substitution of a bromine atom for a hydrogen.