• Diamond
• Graphite
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Organic Chemistry
Organic chemistry is the chemistry of carbon.
• There are three forms of pure carbon
• Buckminsterfullerene
“Bucky Balls”
3
Hydrocarbons
• Organic molecules contain carbon combined with other
elements.
• Organic molecules are grouped into families
• Members of a family share common structural, physical, and chemical
characteristics.
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Alkanes
Alkanes are hydrocarbons that contain only carbon-carbon
single bonds.
• Every carbon atom participates in 4 single bonds, either to
another carbon or to a hydrogen.
• Every hydrogen atom is bonded to a carbon by a single
bond.
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Alkanes
Alkanes are hydrocarbons that contain only carbon-carbon
single bonds.
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Alkanes
• Alkanes in which the carbons are connected in a straight
chain are called normal alkanes.
H H H H H H
H C C C C C C H n-hexane
H H H H H H
H H H H 2-methyl-pentane
H C C C C C H
H H H H H
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Alkanes
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Alkanes
They interact with each other only through London dispersion
forces.
• Note how the boiling points increase with molecular weight.
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Molecule in the News
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Molecule in the News:Melamine
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Organic Molecules in the News!!
http://www.cbc.ca/health/story/2007/09/06/additives-lancet.html?ref=rss
http://www.medpagetoday.com/Psychiatry/ADHD-ADD/tb/6610
Quinoline yellow
Sodium benzoate
Carmoisine
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Alkanes
Alkanes, cannot be named based on their molecular formulas
• For example, all of the molecules shown below share the
same molecular formula, C6H14
(hexacarbon tetradecahydride?)
H H H H H H
H C C C C C C H
H H H H H H
n-hexane
H H H H
H C H H C H H C H H C H
H H H H H H H H H H H H H H
H C C C C C H H C C C C C H H C C C C H H C C C C H
H H H H H H H H H H H H H H H H
H C H H C H
H H
H H H H H H
H C C C C C C H
H H H H H H
n-hexane
H H H H
H C H H C H H C H H C H
H H H H H H H H H H H H H H
H C C C C C H H C C C C C H H C C C C H H C C C C H
H H H H H H H H H H H H H H H H
H C H H C H
H H
H H H H H H
H C C C C C C H
H H H H H H
n-hexane
H H H H
H C H H C H H C H H C H
H H H H H H H H H H H H H H
H C C C C C H H C C C C C H H C C C C H H C C C C H
H H H H H H H H H H H H H H H H
H C H H C H
H H
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Conformations
All of the 3-dimensional models shown below are for the n-
butane.
• They were generated by rotating the central carbon-carbon
bond.
• They all share the same structural formula.
H H H H
H C C C C H
H H H H
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Conformations
All of the 3-dimensional models shown below are for the n-
butane.
• They were generated by rotating the central carbon-carbon
bond.
QuickTime™ and a
Photo - JPEG decompressor
are needed to see this picture.
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Conformations
Switching from one conformation to another does not require
the breaking and making of covalent bonds.
n-butane 2-methylpropane
H
H C H
H H H H
H H
H C C C C H
H C C C H
H H H H
H H H
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Conformations
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Cycloalkanes
In naming these molecules, the prefix cyclo- is used to
indicate the ring:
As Parent Chain As Substituent Group
C3H 6
cyclopropane R cyclopropyl-
C4H 8
cyclobutane R cyclobutyl-
C5H10
cyclopentane R cyclopentyl-
C6H12
R
cyclohexane cyclohexyl-
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Cycloalkanes
The carbon-carbon single bonds for the carbons in a ring are
no longer free to rotate.
• This leads to a new type of isomer
• Since the two structures share the same name, they are
not constitutional isomers.
CH3 CH3 CH3 CH3
1,2-dimethylcyclohexane 1,2-dimethylcyclohexane
H H H H
H H H
H H H H
H H CH3 H
H H H H
CH3 CH3 H CH3
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Cycloalkanes
Isomers which share the same atomic connections, and
therefore, the same IUPAC name are called stereoisomers.
• When this occurs due to restricted rotation about a
covalent bond, they are called geometric isomers
• The prefix cis- and trans- are used to distinguish geometric
isomers.
CH3 CH3 CH3 CH3
cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane
H H H H
H H H
H H H H
H H CH3 H
H H H H
CH3 CH3 H CH3
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Questions
Draw the condensed structural formulas for the following
molecules:
A) 1-ethyl-2-methylcyclopentane
B) 1,1-dimethylcyclobutane
C) 1,1-dimethyl-2-propylcyclopropane
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Alkenes, Alkynes & Aromatic Compounds
The remaining three families of hydrocarbons are
unsaturated.
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Alkenes, Alkynes & Aromatic Compounds
Alkenes are hydrocarbons that contain at least 1 carbon-
carbon double bond.
• Examples:
H H H H
C C C C
H H H CH2 CH2 CH2 CH3
ethene 1-hexene
(ethylene)
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Alkenes, Alkynes & Aromatic Compounds
Alkynes are hydrocarbons that contain at least 1 carbon-
carbon triple bond.
• Examples:
ethyne 1-hexyne
(acetylene)
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Alkenes, Alkynes & Aromatic Compounds
Aromatics are unsaturated ring molecules
• They are often drawn to look like alkenes, but they behave
much differently than alkenes.
• They have an alternating pattern of double and single
bonds within a ring.
• Benzene is an example
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Alkenes, Alkynes & Aromatic Compounds
The physical properties of all hydrocarbons are the same
• No dipole/dipole interactions
• No hydrogenbonding interactions
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Alkenes, Alkynes & Aromatic Compounds
Naming of Alkenes and Alkynes work the same as for
alkanes, with these added rules:
• The parent chain must include both carbons in all double
and triple bonds.
• Pick the longest chain that also contains all double and triple bonds
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Alkenes, Alkynes & Aromatic Compounds
Naming of Aromatics is based on benzene:
• When the molecule is build on benzene, the parent name
is “benzene”.
• There are also many common names used to describe
aromatic compounds.
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Alkenes, Alkynes & Aromatic Compounds
Naming of Aromatics is based on benzene:
• Aromatic compounds can contain multiple aromatic rings
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Alkenes, Alkynes & Aromatic Compounds
Benzo(a)pyrene found in tobacco smoke is converted to
carcinogenic products in the liver (see below) which link to
DNA and cause mutations.
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Practice Quiz 1 KEY
http://www.chem.uwec.edu/Chem150_S07/course/answers/C
150-Quiz-1-key.swf
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Alkenes, Alkynes & Aromatic Compounds
There are many aromatic molecules found in biology
• Some aromatic compounds contain nitrogen and oxygen
atoms
• For example, the nucleotide base Adenine, which is used
to make DNA and RNA
NH2
N
N
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Alkenes, Alkynes & Aromatic Compounds
Like cycloalkanes, some alkenes can have cis and trans
isomers
• This is due to restricted rotation about the double-bond.
• Not all double bonds produce cis and trans isomers
• Each carbon participating in the double bond must have two different
substituents attached to them
A X
C C
B Y
A ≠ B AND X ≠ Y
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Alkenes, Alkynes & Aromatic Compounds
Like cycloalkanes, some alkenes can have cis and trans
isomers
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Alcohols, Carboxylic Acids & Esters
In addition to the four families of hydrocarbons, there are also
many other families of organic molecules.
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Alcohols, Carboxylic Acids & Esters
Functional Group
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Alcohols, Carboxylic Acids & Esters
The carbon-carbon double bonds found in alkenes is an
example of a functional group.
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Alcohols, Carboxylic Acids & Esters
We look now at three families that are distinguished by a
functional group that contains the element oxygen.
Alcohols
• Members of the alcohol family contain a hydroxyl group.
• The hydroxyl group comprises an oxygen with one single
bond to a hydrogen and another single bond to an alkane-
type carbon
H H
H C C O H hydroxyl group
H H
An alkane-type carbon atom
ethanol
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Alcohols, Carboxylic Acids & Esters
We look now at three families that are distinguished by a
functional group that contains the element oxygen.
Carboxylic acids
• Members of the carboxylic acid family contain a carboxylic
acid group
• The carboxylic acid group comprises a hydroxyl group
connected to a carbonyl group:
O O
C + O H C O H
carbonyl group hydroxyl group carboxylic acid group
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Alcohols, Carboxylic Acids & Esters
Carboxylic acids
• The present of the hydroxyl group next to the cabonyl
group completely changes it properties.
• The alcohol hydroxyl group and the carboxylic acid hydroxyl group are
chemically quite different, which is why molecules that have the carboxylic acid
group are placed in a separate family from the alcohols.
• Later in the semester we will learn about some of these chemical differences.
O O
C + O H C O H
carbonyl group hydroxyl group carboxylic acid group
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Alcohols, Carboxylic Acids & Esters
Carboxylic acids
• The carboxylic acid group can be attached to a hydrogen,
an alkane-type carbon, or an aromatic-type carbon:
O H H O O
H C OH H C C C OH C OH
H H
methanoic acid propanoic acid benzoic acid
(formic acid)
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Alcohols, Carboxylic Acids & Esters
We look now at three families that are distinguished by a
functional group that contains the element oxygen.
Esters
• Chemically, esters can be synthesized by reacting a
carboxylic acid with and alcohol:
O O
C O H + H O C C O C + H O H
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Alcohols, Carboxylic Acids & Esters
We look now at three families that are distinguished by a
functional group that contains the element oxygen.
Esters
• Chemically, esters can be synthesize by reacting a
carboxylic acid with and alcohol:
O
CH3 CH2 C O CH2 CH3
Carboxylic Alcohol
acid part part
Ethyl propanoate
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Alcohols, Carboxylic Acids & Esters
Carboxylic acids
• The carboxylic acid group can be attached to a hydrogen,
an alkane-type carbon, or an aromatic-type carbon:
O H H O O
H C OH H C C C OH C OH
H H
methanoic acid propanoic acid benzoic acid
(formic acid)
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Alcohols, Carboxylic Acids & Esters
As we saw with the hydrocarbons, the physical properties of
organic molecules depend on the noncovalent intermolecular
interactions which attract one one molecule to another.
• With hydrocarbons, there is only one type of noncovalent
interaction:
• Induced dipole/Induced dipole (London dispersion force)
52
Alcohols, Carboxylic Acids & Esters
As we saw with the hydrocarbons, the physical properties of
organic molecules depend on the noncovalent intermolecular
interactions which attract one one molecule to another.
• Alcohols and Carboxylic acids also have a hydroxyl group
with a hydrogen bonded to an oxygen. This allows them to
form hydrogen bonds with each other. Therefore,
carboxylic acids have at least three different noncovalent
interactions:
• Induced dipole/Induced dipole (London dispersion force)
• Dipole/Dipole
• Hydrogen bond
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Alcohols, Carboxylic Acids & Esters
To summarize, the types of noncovalent interact ions that
each family can participate in include:
• Hydrocarbons (Alkanes, Alkenes, Alkynes &
Aromatics)
• Induced dipole/Induced dipole (London dispersion force)
• Esters
• Induced dipole/Induced dipole (London dispersion force)
• Dipole/Dipole
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Alcohols, Carboxylic Acids & Esters
These interactions are illustrated in Figure 4.23 of your
textbook.
alcohols
esters
carboxylic acids
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Alcohols, Carboxylic Acids & Esters
Boiling points are a good measure of the strength of the
noncovalent interactions between molecules.
• The stronger the interactions, the higher the boiling point
will be.
• The next slide shows a chart using the data found in Table
4.7 of Raymond, in which the boiling points for alcohols,
carboxylic acids and esters are plotted against molecular
weight.
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Alcohols, Carboxylic Acids & Esters
• As expected, the boiling points
for members of all three
families increases with
molecular weight due to the
London dispersion interactions.
• For a given molecular weight,
• Esters, on the other hand, produce the sweet, often pleasant order associated
with flowers, perfumes and various natural and artificial flavorings. The next
slide shows Figure 4.24 from Raymond, which gives some specific examples.
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Alcohols, Carboxylic Acids & Esters
Examples of some
flavorable esters:
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The End