ORGANIC CHEMISTRY

By
Mubarak O. AMEEN 1
 •Aromatic
Hydrocarbons
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• Aromatic hydrocarbons are benzene and
benzenoids compounds (i.e. compounds
resembling benzene)

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• Benzene C6H6 & benzenoids are unusually stable
because of large electron energies are called
aromatic compounds.
• Compounds like benzene, which have relatively
few hydrogens in relation to the number of
carbons, are typically found in oils produced by
trees and other plants.
• Early chemists called such compounds aromatic
compounds because of their pleasing fragrances.

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• To be classified as aromatic, a compound must meet
the following criteria:
– The compound must be cyclic.
– The molecule must be planar.
– It must have an uninterrupted cyclic cloud of pi electrons
– The cloud must contain an odd number of pairs of
electrons. Hückel’s rule i.e. 4n + 2
• The rule states that “for a planar, cyclic compound to
be aromatic, its uninterrupted cloud must contain (4n
+ 2) pi electrons, where n is any whole number.

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 Nomenclature of substituted Benzenes
• Some monosubstituted benzenes are named
simply by stating the name of the substituent,
followed by the word “benzene.”

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• Some monosubstituted benzenes have names that
incorporate the name of the substituent.
• Unfortunately, such names have to be memorized.

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• With the exception of toluene, benzene rings with
an alkyl substituent are named as alkyl-substituted
benzenes or as phenyl-substituted alkanes.

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 Reactions of Benzene
• Benzene mainly undergoes substitution reactions
• The following are the five most common electrophilic aromatic
substitution reactions:
• Halogenation: A bromine (Br), a chlorine (Cl), or an iodine (I)
substitutes for a hydrogen.
• Nitration: A nitro (NO2) group substitutes for a hydrogen.
• Sulfonation: A sulfonic acid (SO3H) group substitutes for a
hydrogen.
• Friedel–Crafts acylation: An acyl (RC=O) group substitutes for a
hydrogen.
• Friedel–Crafts alkylation: an alkyl (R) group substitutes for a
hydrogen.

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 Study Questions
• Draw the structure of each of the following compounds:
– 2-phenylhexane
– 3-benzylpentane
– benzyl alcohol
– bromomethylbenzene

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 •Alkanol
(Alcohols)
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 Alcohols
• Alcohols are compounds in which a hydrogen of
an alkane has been replaced by an OH group.
• General formula CnH2n+1OH
• Alcohols are classified as primary, secondary, or
tertiary, depending on whether the OH group is
bonded to a primary, secondary, or tertiary
carbon—the same way alkyl halides are classified.

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• The common name of an alcohol consists of the
name of the alkyl group to which the OH group is
attached, followed by the word “alcohol.”

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 Systematic Nomenclature
• The functional group is the center of reactivity in a
molecule.
• In an alcohol, the OH is the functional group.
• The IUPAC system uses a suffix to denote certain
functional groups.
• The systematic name of an alcohol, for example, is
obtained by replacing the “e” at the end of the
name of the parent hydrocarbon with the suffix
“ol.”

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• When necessary, the position of the functional group
is indicated by a number immediately preceding the
suffix.
• However, names with the number preceding the
name of the alcohol have been in use for a long time,
so those are the ones most likely to appear in the
– Literature
– on reagent bottles; and
– on standardized tests.
• They are also the ones that appear most often in most
books.

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• The following rules are used to name a compound
that has a functional group suffix:
The parent hydrocarbon is the longest continuous
chain containing the functional group.
The parent hydrocarbon is numbered in the
direction that gives the functional group suffix the
lowest possible number.

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If there is a functional group suffix and a
substituent, the functional group suffix gets the
lowest possible number.

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If the same number for the functional group suffix is
obtained in both directions, the chain is numbered in
the direction that gives a substituent the lowest
possible number.
Notice that a number is not needed to designate the
position of a functional group suffix in a cyclic
compound, because it is assumed to be at the 1-
position.

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If there is more than one substituent, the
substituents are cited in alphabetical order.

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 Types of alcohol
• Monohydric alcohol: alcohol with one OH group
• Polyhydric alcohol: alcohol with more than one OH
group

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•Do you have
any question?
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 Study questions
• Draw the structures of a homologous series of alcohols that
have from one to six carbons, and then give each of them a
common name and a systematic name.
• Give each of the following compounds a systematic name,
and indicate whether each is a primary, secondary, or
tertiary alcohol:

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 Study questions
• Write the structures of all the tertiary alcohols
with molecular formula C6H14O, and give each a
systematic name.

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 Ethanol
• The most useful alcohol C2H5OH
• It can be prepared by
– Hydrolyzing iodoethane by alkali
– Hydrolyzing ethanal with nascent hydrogen
– Reducing ethanal with nascent hydrogen
• Industrially it can be prepared
– From Ethane
– By fermentation

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 Properties
• It reacts with sodium and potassium to form
ethoxides
– 2C2H5OH + 2Na 2C2H5ONa + H2
• It reacts with phosphorus V chloride to form
hydrogen chloride and chloroethane

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 Uses
• As solvent
• Used to produce halides, etc
• Used as fuel

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 •Any
questions?
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•Carboxylic acids
(Alkanoic acid)
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