1/8/09
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Organic Chemistry
Text: Chapter 26 & Bruice Section (4 weeks)
Topic 1: IUPAC etc.,
1.0 IUPAC nomenclature; Alkanes, Haloalkanes, Alkenes (E/Z), Alkynes,
Ethers, Amines, Alcohols, Ketones, Aldehydes, Amides, Esters, &
Carboxylic Acids
2.0 Organic reactions, Mechanisms and Arrow pushing
3.0 Conformational analysis
4.0 Steriochemistry
From: http://www.dilbert.com
Winter 2009
Page 1
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: IUPAC etc.,
Definition: Some consider any molecule with carbon atoms
as an “organic molecule”, others include only Hydrocarbons.
Natural Organic Compounds, Life and the Original Definition
of an “Organic Chemical”?
Friedrich Wohhler’s (1800-1882, University of Gottingen)
Synthesis of Urea in 1828:
Synthetic Organic Compounds: Drugs, Plastics, Explosives,
Pesticides etc.
Winter 2009
Page 2
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
WILD AND INTERESTING THINGS LIKE:
Bisphenol A
Winter 2009
Topic 1: IUPAC etc.,
cocaine
heroin
Methamphetamine
Page 3
1
1/8/09
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: IUPAC etc.,
mustard gas
Tetrodotoxin (puffer fish toxin)
Winter 2009
Page 4
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
REALLY USEFUL THINGS LIKE:
ethanol
Topic 1: IUPAC etc.,
morphine
Resveratrol
Winter 2009
Page 5
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: IUPAC etc.,
the “pill”
viagra
Do you eat “organic food” as a lifestyle choice in order to avoid pesticides?
Winter 2009
Page 6
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1/8/09
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: IUPAC etc.,
Can anyone tell me based on what they have learned so far, which would
have the higher melting point, heroine or bisphenol A? Can you draw the
structure ? What about acid or base characteristics?
On the other hand, what about ;
4,4'-dihydroxy-2,2-diphenylpropane compared to
(5!,6!)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate
Bisphenol A
melts: 159 C
boils: 220 °C/4 mmHg
heroin
Winter 2009
melts: 173 C
boils: 272-274 C
Page 7
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: IUPAC etc.,
International Union of Pure and Applied Chemistry (IUPAC): is an
international non-governmental organization established to set consistent
and universal standards for scientifically important conventions such as
naming chemical structures.
Very good online resources:
•!http://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemistry
•!http://www.acdlabs.com/iupac/nomenclature/
Winter 2009
From: http://www.dilbert.com
Page 8
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: IUPAC etc.,
Basic principles
In IUPAC nomenclature, a number of prefixes, suffixes and infixes are used to
describe the type and position of functional groups in the compound.
The steps to naming an organic compound are:
•!Identify the parent hydrocarbon chain (longest continuous carbon chain)
•!Identify the functional group, if any
•!Identify the position of the functional group
•!Functional group should have the lower number
•!The number is written before the name of the functional group suffix
(such as -ol, -one, -al, etc.). Terminal-only group, need not be numbered
•!Identify the side-chains and number them.
•!Identify the remaining functional groups,
•!Identify double/triple bonds. Number them with the number of the carbon
atom before them.
•!Add punctuation: commas between numbers; hyphens between numbers
and letters; and successive words are merged into one word (trimethyl
hexane becomes trimethylhexane)
Winter 2009
Page 9
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1/8/09
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Alkanes:
Alkanes are hydrocarbons (contain only C&H) linked exclusively by single bonds
(i.e., they are saturated compounds) without any cyclic structure. Alkanes
belong to a homologous series of organic compounds in which the members
differ by carbon number.
Each carbon atom must have 4 bonds (either C-H or C-C bonds), and each
hydrogen atom must be joined to a carbon atom (H-C bonds). A series of linked
carbon atoms is known as the carbon skeleton or carbon backbone. The number
of carbon atoms is used to define the size of the alkane
•!linear (general formula CnH2n+2)
•!branched (general formula CnH2n+2, n>3)
•!cyclic (general formula CnH2n, n>2) IUPAC = cycloalkanes.
The simplest possible alkane (the parent molecule) is methane, CH4.
Winter 2009
Page 10
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Alkane nomenclature:
Straight-chain alkanes take the suffix "-ane" and are prefixed depending on the
number of carbon atoms in the chain;
Prefix
1:Meth 2:Eth
3:Prop 4:But
5:Pent 6:Hex 7:Hept 8:Oct
9:Non
10:Dec 11: Undec 12: Dodec 13:Tridec 14: Tetradec 15:Pentadec 20:Eicos
For example: CH4 is methane, and CH3(CH2)6CH3 is octane.
The names of the first four alkanes were derived from methanol, ether, propionic
acid and butyric acid, respectively. The rest are named with a Greek numeric
prefix, with the exceptions of nonane which has a Latin prefix, and undecane and
tridecane which have mixed-language prefixes.
Winter 2009
From: http://www.dilbert.com Page 11
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Winter 2009
Page 13
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Winter 2009
Page 14
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Alkyl substituent (alkyl group) is a “function group” consisting of an alkane less one
hydrogen. This is sometimes given the symbol “R”.
From: http://www.dilbert.com
Winter 2009
Page 15
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1/8/09
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Winter 2009
Page 16
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Common Names in Red; IUPAC name in Blue
Winter 2009
Page 17
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkanes
Alkanes Applications and uses:
•! Methane and ethane are the main components of natural gas
•! Propane and butane are liquified petroleum gas (LPG) also propellants in
aerosol sprays.
•! Pentane to octane are volatile liquids. They are used as fuels in internal
combustion engines. These are also good solvents for nonpolar substances.
•! Nonane to hexadecane are major part of diesel and aviation fuel.
•! Hexadecane is an important components of fuel oil and lubricating oil.
•! High molecular weight alkanes are solids used as paraffin wax, in candles.
•! Synthetic polymers such as polyethylene and polypropylene are alkanes
with chains containing hundreds of thousands of carbon atoms.
Winter 2009
http://www.3dchem.com/3dmolecule.asp?ID=331
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Functional Groups
Functional Groups:
Common connections of atoms in a molecule lead to similar geometry, polarity
and other similar properties. This similarity in chemical nature makes it
convenient to group “functional” groups together as they have similar chemistries
and related properties. For example;
Can you suggest some properties that these groups may have in common?
From: http://www.dilbert.com
Page 19
Winter 2009
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Naming alcohols, amines, halides and ethers
Red = Oxygen, Blue = Nitrogen
A) Propanol
B) Dimethyl Ether
C) Propylamine
Winter 2009
Page 20
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Primary, secondary and tertiary Carbon
“Carbon” type:
Carbon atoms within a molecule can be classified by the number of other carbon
atoms they are connected to. A primary carbon is one that is connected to only
one other carbon, a secondary carbon is attached to two other carbon and a
tertiary carbon is attached to 3 other carbon atoms.
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Primary, secondary and tertiary Carbon and Hydrogen
Hydrogen atoms are classified by the Carbon they are connected to.
Winter 2009
Page 22
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkane nomenclature
1) Longest chain is Parent compound
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
2) Place substituent name before parent
Winter 2009
Topic 1: Alkane nomenclature
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
3) Use name with lowest possible numbers
Topic 1: Alkane nomenclature
Winter 2009
Page 25
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
3) Use name with lowest possible numbers
Topic 1: Alkane nomenclature
Winter 2009
Page 26
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
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3) Use name with lowest possible numbers
Winter 2009
Topic 1: Alkane nomenclature
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
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Topic 1: Alkane nomenclature
4) Cite groups alphabetically, lowest # first
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Page 28
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkane nomenclature
5) maximize # of substituents
From: http://www.dilbert.com
Winter 2009
Page 29
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
6) Some common names acceptable for substituents
Topic 1: Alkane nomenclature
Do problems 7 – 10 in text.
From: http://www.dilbert.com
Winter 2009
Page 30
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Cycloalkane nomenclature
Cycloalkanes are alkanes which have one or more rings of carbon atoms in the
chemical structure of their molecules. A general chemical formula for cycloalkanes
is CnH2(n+1-g) where n = number of C atoms and g = number of rings in the
molecule. Cycloalkanes are named analogously to their normal alkane
counterpart of the same carbon count: cyclopropane, cyclobutane, cyclopentane,
cyclohexane, etc.
Skeletal structures
Winter 2009
Page 31
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Cycloalkane nomenclature
If two or more substituents, list alphabetically and give #1 to substituent
listed first.
Winter 2009
Page 32
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Cycloalkane nomenclature
When naming arrange so that numbers are as small as possible
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Cycloalkane nomenclature
Cycloalkanes are similar to alkanes in physical properties, but they have higher
boiling points, melting points, and densities. This is due to stronger London forces
because the ring shape allows for a larger area of contact. Cycloalkanes exhibit
almost the same degree of unreactivity as alkanes, due to their containing only
unreactive C-C and C-H bonds; however, ring strain can cause increased
reactivity.
Winter 2009
Page 34
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkyl Halides
Alkyl Halides are alkane like compound where one or more hydrogen atoms
have been replaced by a halide. The attached halide can be classified as primary,
secondary or tertiary in the same manner as alkane hydrogens. The lone pairs on
the halogens and their electronegativity provide unique chemistry. For naming add
the name of the halogen less the “ine” part as a prefix to the alkane name. For
Example:
Winter 2009
Page 35
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkyl Halides
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Ethers
Ethers are compounds that have two alkyl groups bound together by an oxygen
atom. Common names for ethers are the two alkyl group names, in alphabetical
order followed by the word ether. IUPAC names add an oxy suffix in place of the
“yl” suffix of the shortest alkyl group and then name as a alkane substituent.
Winter 2009
Page 37
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Ethers
Winter 2009
Page 38
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alcohols
Alcohols are alkane like compound where one or more hydrogen atoms have
been replaced by an OH group. Alcohols can be classified as primary, secondary
or tertiary in the same manner as alkane hydrogens. The potential hydrogen
bonding due to the OH group results in large intermolecular forces. To name, add
an “ol” suffix in place of the “yl” suffix in the alkyl group name.
Winter 2009
From: http://www.dilbert.com
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alcohols
Winter 2009
Page 40
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alcohols
Winter 2009
Page 41
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alcohols
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alcohols
Winter 2009
Page 43
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Amines
Amines are compounds where one or more hydrogens of an ammonia molecule
have been replaced by an alkyl group. Primary, secondary or tertiary terms refer
to how many alkyl groups are bound the nitrogen. To name, state the alkyl group
(s) bound to the nitrogen followed by the word amine.
Winter 2009
Page 44
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Amines
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
Winter 2009
http://people.ok.ubc.ca/orcac/chem123out.html
From: http://www.dilbert.com Page 46
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Amines
Quaternary ammonium salts occur when four alkyl groups are bound to a
nitrogen so that the nitrogen has a formal charge of +1.
Winter 2009
From: http://www.dilbert.com
Page 47
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Amines
Quaternary ammonium salts occur when four alkyl groups are bound to a
nitrogen so that the nitrogen has a formal charge of +1.
Winter 2009
From: http://www.dilbert.com
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
Alkenes and Alkynes are hydrocarbons containing at least one double bond
(alkene or olefin) or a triple bond (alkyne). These compounds have less
hydrogen than alkanes and thus are called unsaturated. A simple alkene has only
one double bond and the general formula CnH2n. A simple alkyne has the formula
CnH2n-2. To name an alkene replace the “yl” suffix of an alkyl group with “ene” To
name an alkyne replace the “yl” suffix of an alkyl group with “yne”.
Winter 2009
Page 49
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
Winter 2009
Page 50
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
If an Alkene has two double bonds use the suffix “diene”. For Example;
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
Recall bonding concepts: Ethene
In Butene, 2 distinct isomers exist
Winter 2009
Page 52
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
Alkenes can also be classified by the geometry of the items bound to the double
bond. Since double bonds do not permit free rotation, geometric structural
isomers exist. For Example;
Winter 2009
Page 53
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
The cis and trans naming of alkenes is valid when at least two substituents are
the same. But what about when all are different?
The E,Z system.
Winter 2009
Page 55
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
The E,Z System sets priority using the following rules.
1.! Greater atomic number, higher the priority. Based on atom to sp2 Carbon.
2.! For ties, move out to next bound atoms
3.! Consider double bonds to be connected to 2 of the atoms bonded and triple to
three
4.! higher mass isotopes have a higher priority than lower isotopes.
Winter 2009
Page 56
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
The E,Z System sets priority using the following rules.
1.! Greater atomic number, higher the priority. Based on atom to sp2 Carbon.
2.! For ties, move out to next bound atoms
3.! Consider double bonds to be connected to 2 of the atoms bonded and triple to
three
4.! higher mass isotopes have a higher priority than lower isotopes.
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Alkenes and Alkynes
The E,Z System sets priority using the following rules.
1.! Greater atomic number, higher the priority. Based on atom to sp2 Carbon.
2.! For ties, move out to next bound atoms
3.! Consider double bonds to be connected to 2 of the atoms bonded and
triple to three
4.! higher mass isotopes have a higher priority than lower isotopes.
Winter 2009
Page 58
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Aromatic Hydrocarbons
Aromatic Hydrocarbons are hydrocarbons containing aromatic rings such as
benzene. Typically all the carbons are in the same plane and the pi orbitals of the
carbon can interest in extended molecular orbitals.
Winter 2009
Page 59
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Aromatic Hydrocarbons
When a benzene ring is a substituent species, it is called a Phenyl ring. There
are a number of well established common names for aromatic species and a few
are presented below and on the previous slide.
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Aromatic Hydrocarbons
For compounds such as Toluene that contains a substituent, the ring position it is
connected to is called position 1. For biphenyl this is the linking bond between the
two rings. For mixed substituents, list alphabetically and number the first
substituent as 1.
The terms ortho, meta and para (o-, m-, p-) can be used with a benzene ring
with two substituents. Ortho being on adjacent carbons, meta are one carbon
apart and para are on opposite sides.
Winter 2009
Page 61
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Phenols
Both Alcohols and Phenols are characterized by the presence of a hydroxyl
group. Phenols are attached to an aromatic ring. Naming is identical to other
substituted aromatics such as Toluene.
Winter 2009
Page 62
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Aldehydes and Ketones
Both Aldehydes and Ketones contain a carbonyl group, or a carbon with a
double bonded to oxygen. If one of the other substituents bound to the carbon is
a hydrogen, the compound is called an aldehyde. If both substituents are alkyl or
aromatic groups the compound is a ketone.
Winter 2009
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Topic 1: Organic Chemistry
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Topic 1: Aldehydes and Ketones
The IUPAC naming for an Aldehyde replaces the alkyl suffix with “-al” or adds the
aldehyde extension for phenolics. Ketones use the suffix “-one”. The parent alkyl
group includes the carbonyl carbon and this is numbered to be as low as possible.
Winter 2009
Page 64
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Carboxylic Acids
Carboxylic acids contain a carbonyl group and a hydroxyl group joined together.
The hydrogen of the hydroxyl group is quite acidic and can be removed by bases
to form carboxylic acid salts.
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
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Topic 1: Carboxylic Acids
Carboxylic acids contain a carbonyl group and a hydroxyl group joined together.
The hydrogen of the hydroxyl group is quite acidic and can be removed by bases
to form carboxylic acid salts.
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
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Topic 1: Amide
Amide contain a carbonyl group and a hydroxyl group joined together nitrogen
atom (N), usually as NH2. Amides are commonly formed from the reaction of a
carboxylic acid with an amine. This is the reaction that forms peptide bonds
between amino acids. These amides can participate in hydrogen bonding as
hydrogen bond acceptors and donors.
Winter 2009
Page 67
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Winter 2009
Page 68
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
Winter 2009
http://people.ok.ubc.ca/orcac/chem123out.html
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Winter 2009
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Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
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Topic 1: Organic reactions etc
Reactions of Alkanes: In general saturated hydrocarbons are unreactive. They
are non-polar and generally insoluble in water. At higher temperature or under the
influence of UV light substitution reactions occur.
heat or
light
Initiation:
Cl-Cl
Propagation:
H3C-H + Cl•
H3C• + H-Cl
H3C• + Cl-Cl
H3C-Cl + Cl•
Termination:
2Cl•
Cl• + Cl•
Cl-Cl
H3C• + Cl•
H3C-Cl
H3C• + H3C•
H3C-CH3
Winter 2009
Page 71
Chemistry 123: Physical and Organic Chemistry
Topic 1: Organic Chemistry
http://people.ok.ubc.ca/orcac/chem123out.html
Topic 1: Organic reactions etc
Reactions of Alkanes: The most common and useful reaction of alkanes is
oxidation also known as burning.
C8H18 + 25/2 O2(g)
8CO2(g) + 9H2O(l)
!Hº = -5.48 x 103 kJ
Why is this reaction so useful in combustion engines?
Winter 2009
From: http://www.dilbert.com
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