Chapter 1&2, Org. Chem. I, Fall '08
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Lecture Outline
q
Organic Chemistry
q
Relationship of Structure, Energy, and Reactivity
q
Bonding
q
Representing molecules (putting the atoms together)
o Lewis and Kekulé Structures
o Line-angle Formula
o 3-D
qFunctional Groups
q Naming organic compounds
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Organic Chemistry
What: The study of carbon-containing compounds
Why: Pervasive in nature; Life is based on organic compounds
Chemical foundation of biology
Improve standard of living (medicines, plastics pesticides
. . .)
How: Examine structure and analyze how it governs reactivity
STRUCTURE Determining the Way in Which Atoms Are Put Together in
Space to Form Complex Molecules
MECHANISM Understanding the Reactivity of Molecules: How and Why
Chemical Reactions Take Place
SYNTHESIS Building Complex Molecules From Simple Molecules Using
Chemical Reactions
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Structure
Foundation of organic chemistry
1. What atoms (besides carbon) are important?
2. How are these atoms bonded together?
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Summary of Bonding
Neutral atoms
Charged atoms
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Representing Molecules
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Examples in order to familiarize with functional groups
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Isomerism
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Classifying sp3 Atoms by Connectivity I I
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Classifying sp3 Atoms by Connectivity II
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Examples of Classifying Atoms
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Systematic name of most organic compounds
Formula
Alkene
propene
Alkyne
Alcohol
IUPAC name
ethyne
CH3OH
methanol
Formula
IUPAC name
O
propanoyl
chloride
Acyl
chloride
Acid
anhydride
Cl
O
Ethanoic
propanoic
anhydride
O
O
Ester
Ethyl ethanoate
O
O
Ether
ethoxyethane
Amide
O
Aldehyde
Butanamide
O
NH2
O
ethanal
Nitrile
cyclohexanone
Nitro
compound
CH3NO2
Nitromethane
Butanoic acid
Alkyl
halide
CH3Br
bromomethane
N
Pentanenitrile
H
Ketone
Carboxylic
acid
O
O
OH
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Summary of rules for naming alkanes, alkyl halides and ethers
1.
Find the longest continuous chain of carbon atoms, and use this chain as the
name of the compound.
2.
Number the longest chain beginning with the end of the chain nearest a
branch.
3.
Name the substituent groups attached to the longest chain as alkyl groups.
Give the location of each alkyl group by the number of the main-chain carbon
atom to which is its attached.
4.
When two or more substituents are present, list them in alphabetical order.
When two or more of the same alkyl substituent are present, use the prefixes
di-, tri-, tetra-, and so on (ignored in alphabetizing), to avoid having to name
the alkyl group twice.
5.
Alkyl halides and ethers are named as substituted alkanes.
X-: “halo-”; RO-: “-oxy”
6. The parent hydrocarbon is numbered in the direction that gives the
functional group substituent the lowest possible number.
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Summary of rules for naming a compound with a functional group suffix
1.
2.
3.
4.
5.
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.
If there is a functional group suffix and a substituent, the functional
group suffix gets the lowest possible number.
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.
If there is more than one subtituent, the substituents are cited in
alphabetical order.
[Substituent]-[Parent Hydrocarbon]-[Functional Group Suffix]
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Important structures to learn
acetone
Me
Me
ether or
diethyl ether
O
acetaldehyde
O
pyridine
N
H
O
formic acid
OH
phenol
Me
H
acetic acid or
AcOH
Me
toluene
O
OH
O
Me
OH
THF
(tetrahydrofuran)
DMF
(dimethylformamide)
O
Me
Me
N
H
O
benzene
ethyl acetate
or EtOAc
DMSO
(dimethylsulfoxide)
O
EtO
Me
Me
O
S
Me
chloroform
CHCl3
Methylene chloride
CH2Cl2
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