‫به نام خدا‬
‫شیمی آلی ‪2‬‬
1. McMurry, Organic Chemistry, 7th ed., Brooks/Cole,
Monterey CA, 2008.
2. Morrison and Boyd, Organic Chemistry, 6th ed.,
Benjamin Cummings, CA, 1992.
3. Carey, Organic Chemistry, 6th ed., McGraw-Hill, NY,
2006.
4. Vollhardt and Schore, Organic Chemistry, 4th ed.,W.H.
Freeman, New York, 2002.
5. Streitwieser, Heathcock, and Kosower, Introduction to
Organic Chemistry, 4th ed.; Prentice-Hall, Saddle River, NJ,
1998.
6. Sykes, A Guidebook to Mechanism in Organic Chemistry,
6th ed., Longmans Scientific and Technical, Essex, 1986.
‫کوئیز‪25 :‬نمره‬
‫نظم و ترتیب و حضور و غیاب‪15 :‬نمره‬
‫امتحان نیم ترم‪60 :‬نمره‬
‫امتحان آخر ترم‪100 :‬نمره‬
‫شیمی آلی‬
‫جلد دوم‬
‫ترجمه‪ :‬دکترعیسی یاوری‬
‫نشر نوپردازان ‪ -‬تهران ‪1391‬‬
Organic Chemistry 2
15 Benzene and Aromaticity
16 Chemistry of Benzene: Electrophilic Aromatic Substitution
17 Alcohols and Phenols
18 Ethers and Epoxides; Thiols and Sulfides
> A Preview of Carbonyl Compounds
19 Aldehydes and Ketones: Nucleophilic Addition Reactions
20 Carboxylic Acids and Nitriles
21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
Reactions
5
15. Benzene and
Aromaticity (1)
Based on McMurry’s Organic Chemistry, 7th edition
Aromatic Compounds
 Aromatic was used to described some fragrant
compounds in early 19th century

Not correct: later they are grouped by chemical
behavior (unsaturated compounds that undergo
substitution rather than addition)
 Current: distinguished from aliphatic compounds by
electronic configuration
coal distillate
cherries,
peaches,
and almonds
Tolu balsam
7
steroids
Cholesterol
lowering
drug
8
Leucine follows the same steps, up to the FAD dependent acyl CoA dehydrogenase.
At this point the product is branched on C-3, and hydration would produce a
tertiary alcohol which could not be oxidized further. Instead, one of the terminal
methyl groups is carboxylated, being activated by the C=O through the conjugated
double bond. The carboxylated product is then hydrated, giving the tertiary alcohol
hydroxymethylglutaryl-CoA, HMG-CoA, which splits into acetoacetate and
acetyl-CoA (or could potentially be reduced to mevalonate).
Why this Chapter?
 Reactivity of substituted aromatic compounds
is tied to their structure
 Aromatic compounds provide a sensitive
probe for studying relationship between
structure and reactivity
14
15.1 Sources and Names of
Aromatic Hydrocarbons
 From high temperature distillation of coal tar
 Heating petroleum at high temperature and pressure
over a catalyst
Some aromatic hydrocarbons found in coal tar
15
two large reservoirs of organic
Aromatic compounds are
separated as such from
coal tar
Coal
Aromatic compounds are
synthesized from the
alkanes of petroleum
petroleum
absence
of air
a ton of soft coal
volatile compounds
material
residue
catalytic reforming
dehydrogenation
cyclization
isomerization
hydrodealkylation
coke
coal tar
60 kg
distillation
smelting of iron to steel
coal gas
benzene, 1 kg
toluene, 250 g
xylenes, 50 g
phenol, 250 g
cresols, 1 kg
naphthalene, 2.5 kg
benzene
toluene
xylenes
Discovery and early theories of
benzene’s structure
 Discovered by Michael Faraday (1825)
 Analysis showed a molecular formula of
C6H6
1829-1896
 Many structures were proposed,
culminating with Kekule’s “cyclohexatriene” of 1865.
 Kekule realized that the ring bonds must be identical,
proposing a rapid equilibration.
 These are now described as resonance forms of
benzene.
17
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