Lecture #13: CHE202/BBT202 SPRING 2020

CHE202/BBT202 SPRING 2020
MSH3
Bio-Organic Chemistry
Lecture #13
McMurry
Organic Chemistry
Chapter 15
Benzene & Aromaticity
Aromatic Compounds
Q1. Give three examples of aromatic compounds with fragrance.

Q2. Write four characteristics of aromatic compounds.
Aromatic Compounds
The word aromatic refers to the class of compounds that contain
six-membered benzene-like rings with three double bonds.
Many naturally occurring compounds are aromatic in part, including steroids
such as estrone and well-known pharmaceuticals such as the cholesterol-
lowering drug atorvastatin, marketed as Lipitor. Benzene itself causes a
depressed white blood cell count (leukopenia) on prolonged exposure and
should not be used as a laboratory solvent.
Q1. Give modern definition of aromatic compounds.

Q2. Name two aromatic compounds.
No question on the structures on this slide in exam.
Sources of Aromatic Compounds
Q1. What are the two main sources of simple aromatic compounds?
Q2. Draw structures of three aromatic hydrocarbons found in coal tar.
Sources of Aromatic Compounds
http://www.engineersindia.com/petroleumrefining/m-27
http://www.worldofchemicals.com/42/chemistry-articles/vladimir-nikolayevich-ipatieff-modern-petroleum-chemist.html
https://www.britannica.com/technology/petroleum-refining/Polymerization-and-alkylation Q1. How aromatic compounds are made by refining petroleum?

No question in exam from the images of this slide.
Common Names of Aromatic Compounds
Q1. Draw structures of toluene, phenol, aniline, benzaldehyde, Benzoic acid, ortho-Xylene.
Naming alkyl-substituted and monosubstituted Benzenes
Q1. Draw the structures of phenyl group, benzyl group.

Q2. Name and draw the structure of a monosubstituted benzene.
Naming disubstituted Benzenes
Q1. Explain nomenclature of disubstituted benzenes by ortho-, meta-, para- system with examples.
Naming of tri- or more substituted Benzenes
Q1. Explain nomenclature of benzenes with more two substituents with examples.
Structure and Stability of Benzene: Unusual properties of benzene
Q1. Discuss reaction of benzene with bromine.

Difference in the brominations of benzene and alkenes
Alkene Addition
Benzene Substitution
Q1. Discuss how the bromination reactions differ between benzene and an alkene.
Benzene has no double bond
All of the carbon–carbon bonds of benzene have the same length—139 pm—intermediate between typical single
(154 pm) and double (134 pm) bonds. In addition, an electrostatic potential map shows that the electron density in all
six C-C bonds is identical. Thus, benzene is a planar molecule with the shape of a regular hexagon.
Q1. Discuss the nature of carbon-carbon bonds in benzene.

Q2. How many double bonds are there in benzene?
Q3. Draw the most appropriate representation of the structure of benzene.
Aromaticity and the Hückel 4n+2 rule
According to a theory devised in 1931 by the German physicist Erich Hückel, a

molecule is aromatic only if it has a planar, monocyclic system of conjugation and
contains a total of 4n+2 π electrons, where n is an integer (n = 0, 1, 2, 3, . . .).
In other words, only molecules with 2, 6, 10, 14, 18, . . . π electrons can be
aromatic.
Q1. Write three properties of benzene.
Q2. What is Hückel rule?
Aromatic Heterocycles: Pyridine and Pyrrole
Q1. What is a
heterocycle?
Q2. Are pyridine and
pyrimidine aromatic?
Draw orbitals to
explain your answer.
Aromatic Heterocycles: Pyridine and Pyrrole
Q1. Draw the structure of a five-

membered heterocyclic aromatic
compound.
Q2. Are pyrrole and imidazole
aromatic? Draw orbitals to explain
your answer.
Aromatic Heterocycles: Pyrimidine and Imidazole rings in biological compounds
Q1. Draw structures of a biological compound

with (i) a pyrimidine, (ii) an imidazole ring.
Polycyclic Aromatic Compounds
Polycyclic aromatic hydrocarbons (PAHs) are a group of more than 100

different chemicals that are released from burning coal, oil, gasoline,
trash, tobacco, wood, or other organic substances such as charcoal-
broiled meat.
Q1. Draw the structures of two polycyclic aromatic compounds.

Polycyclic Aromatic Compounds: Naphthalene
Q1. Draw the resonance forms of naphthalene.

Q2. Show the bromination reaction of naphthalene.
Polycyclic Aromatic Compounds: Naphthalene
Q1. Draw orbital structures to explain aromaticity of naphthalene.

Heterocyclic Analogues of Naphthalene
Q1. Draw the structure of an aromatic heterocyclic analogue of naphthalene.

(Suggestion: Indole, Purine)
Polycyclic Aromatic Compounds: Biological examples
Q1. Draw the structures of two biological compounds with polycyclic

aromatic rings. (Suggestion: Tryptophan, Adenine, Guanine)
Next Lecture:
Chemistry of Benzene:
Electrophilic Aromatic Substitution
Reference Textbook:
Organic Chemistry, 8th Edition
John McMurry, Chapter 16
Brooks/Cole Cengage Learning,
Belmont, CA, USA

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CHE202/BBT202 SPRING 2020

Q1. Give three examples of aromatic compounds with fragrance.

Q1. Give modern definition of aromatic compounds.

https://www.britannica.com/technology/petroleum-refining/Polymerization-and-alkylation Q1. How aromatic compounds are made by refining petroleum?

Q1. Draw the structures of phenyl group, benzyl group.

Q1. Discuss reaction of benzene with bromine.

Q1. Discuss the nature of carbon-carbon bonds in benzene.

According to a theory devised in 1931 by the German physicist Erich Hückel, a

Q1. Draw the structure of a five-

Q1. Draw structures of a biological compound

Polycyclic aromatic hydrocarbons (PAHs) are a group of more than 100

Q1. Draw the structures of two polycyclic aromatic compounds.

Q1. Draw the resonance forms of naphthalene.

Q1. Draw orbital structures to explain aromaticity of naphthalene.

Q1. Draw the structure of an aromatic heterocyclic analogue of naphthalene.

Q1. Draw the structures of two biological compounds with polycyclic

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