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Dino Spencer S.

Pabilico August 17, 2017


11-Pascal Mrs. Marasigan

ASSIGNMENT

1. What are aromatic compounds? Describe the sources and characteristics of aromatic
compounds.
Aromatic compounds, originally named because of their fragrant properties,
are unsaturated hydrocarbon ring structures that exhibit special properties, including
unusual stability, due to their aromaticity. Some compounds are chemically aromatic
but do not have a distinct smell. Aromatic compounds are generally nonpolar and
immiscible with water. As they are often unreactive, they are useful as solvents for
other nonpolar compounds. Due to their high ratio of carbon to hydrogen, aromatic
compounds are characterized by a sooty yellow flame. Aromatic compounds are
produced from a variety of sources, including petroleum and coal tar. Poly-aromatic
hydrocarbons are components of atmospheric pollution and are known carcinogens.
Aromatic compounds are also interesting because of their presumed role in the origin
of life as precursors to nucleotides and amino acids. Typical aromatic compounds
are benzene and toluene.

2. Describe the structure and stability of aromatic compounds.


These carboxylic compounds contain at least one benzene ring i.e., a ring of six carbons
atoms with alternate double and single bonds. Aromatic compounds are cyclic
structures in which each ring atom is a participant in a *\π bond, resulting in
delocalized *\π electron density on both sides of the ring. Due to this connected
network of *\π bonds, the rings are planar, unlike the boat or table structures typical
of cycloalkanes. The proposed structures for benzene are as follows: Open Chain
structure, Ring structure, Resonance Hybrid structure, and the Orbital structure.
Aromatic molecules are very stable, and do not break apart easily to react with other
substances. Organic compounds that are not aromatic are classified as aliphatic
compounds—they might be cyclic, but only aromatic rings have special stability
(low reactivity). The double bonds in aromatic compounds are less likely to participate
in addition reactions than those found in typical alkenes. When benzene participates in
such substitution reactions, the product retains the stability associated with the
aromatic *\π electron system. This stability is lost in electrophilic addition because the
product is not aromatic.

3. Enumerate the reactions of aromatic compounds.


a. Aromatic Substitution
An example of an aromatic substitution reaction is shown below. In the presence of
strong sulfuric and nitric acid, a nitro group can be added to the ring.
b. Nucleophilic Aromatic Substitutions
In a nucleophilic aromatic substitution reaction, a nucleophile displaces a substituent
on an aromatic ring. The replaced species is typically a good leaving group,
like nitrogen gas or a halide ion. The presence of an electron-withdrawing group on the
ring can speed up the progress of this class of reactions. Chemically, this is similar to
an addition reaction to a Michael acceptor or other electron-deficient, unsaturated
system, followed by an elimination reaction.
c. Electrophilic Aromatic Substitutions
In an electrophilic aromatic substitution reaction, a substituent on an aromatic ring is
displaced by an electrophile. These reactions include aromatic nitration,
aromatic halogenation, aromatic sulfonation, and Friedel-Crafts acylations and
alkylations. These reactions can involve a resonance-stabilized carbocation
intermediate known as a sigma complex. The reactivity can be thought of in terms of
an alkene attacking a cationic species, such as in the first step of an acid-catalyzed
hydration of an alkene.
A number of patterns have been observed regarding the reaction of substituted benzene
rings. These observations have been generalized to provide a predictive rule for
electrophilic aromatic substitutions. It states that an electron-donating substituent
generally accelerates substitution and directs reactivity toward the positions that
are ortho and para to it on the ring, while an electron-withdrawing substituent will slow
reaction progress and favor its meta position on the ring.
d. Coupling Reactions
Coupling reactions are reactions involving a metal catalyst that can result in the
formation of a carbon-carbon bond between two radicals.
e. Hydrogenation
Hydrogenation can be used to create a fully saturated ring system. This is similar to
the hydrogenation of an alkene to form an alkane, albeit more difficult due to the
stability of the aromatic system.