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ORGANIC CHEMISTRY
Forms of Carbon

Carbon has four different allotropes.

Allotropes: Forms of the same element with different bonding
patterns.
1. Diamond
- Carbon is bonded to four other carbon atoms in a tetrahedral pattern
2. Graphite
- Carbon atoms are arranged in sheets or layers
3. Amorphous:
-Not arranged in any predictable shape
- Produced when carbon decomposes
4. Fullerenes
- Globe-shaped, cage like arrangements of carbon atoms
ORANGIC COMPOUNDS
•A compound that is composed of carbon and hydrogen.
•It may also contain atoms of other elements, such as oxygen, nitrogen,
sulfur, and chlorine.
Hydrocarbons:
Basic organic compounds contain only carbon and hydrogen.
Substituted hydrocarbon:
Used when other elements are also present in addition to carbon and
hydrogen.
Carbon atoms have the unique property of being able to bond to each other
and form long "chains" of carbons, or to form circular "rings" of carbons.
The addition of one atom of a different element makes an entirely new
compound is the reason that there are millions of organic compounds in
the world.
The simplest hydrocarbon is methane, which is made of one carbon atom
surrounded by four hydrogen atoms.
Aliphatic Hydrocarbons
Aliphatic hydrocarbons:
The simplest hydrocarbons are those whose carbons are joined in line one to
another.
Alkanes
1. First group
2. Name of each of these compounds ends in "-ane"
3. They have the generic formula of CnH2n+2
4. They have a single covalent bond between them
Also called saturated hydrocarbons, which means that all of the carbons
have the maximum number of bonds (4).
The first ten alkanes should be memorized, because their names are the
basis for most of the naming of the rest of the organic compounds.
1. CH4 : methane
2. C2H6: ethane
3. C3H8: propane
4. C4H10: butane
5. C5H12: pentane
6. C6H14: hexane
7. C7H16: heptane
8. C8H18: octane
9. C9H20: nonane
10. C10H22: decane
Aliphatic Nomenclature
ALKANES
ALKANE NOMENCLATURE
1. Determine the longest continuous chain of carbon. (Parent chain)
2. Number carbons in parent chain. Do this by starting at the end that gives
the attached groups the smallest number.
3. Add numbers to the names of the attached groups to identify their
position. Numbers become prefixes to the name of the parent.
4. Use prefixes to indicate if more than one of the same attached group is
present.
5. List attached groups in alphabetical order. Ignore prefixes.
6. Use commas to separate the numbers, hyphens to separate the numbers
& words. The name of the alkane is written as one word.
Common Alkyl Groups
1. Methyl
2. Ethyl
3. n-propyl
CH3
CH2CH3
CH2CH2CH3
Common Alkyl Groups
4. n-Butyl
CH2CH2CH2CH3
5. Isopropyl CH3CHCH3
Common Alkyl Groups
6. t-Butyl
CH3
C
CH3
CH3
Common Alkyl Groups
7. Amino
NH2
8. Nitro
NO2
9. Bromo
Br
Common Alkyl Groups
10. sec-Butyl
H
CH3
C
CH2
CH3
Examples
CH3
A.
CH3
C
CH2
CH3
H
2-methylbutane
B.
NO2
Br
CH3
CH
CH
CH3
2-bromo-3-nitrobutane
C.
2,2,4-trimethylhexane
CH3
CH3
CH3
C
CH3
CH2
CH
CH2
CH3
ALKENES
1. Next group of hydrocarbons
2. The carbon chain has a double covalent bond
3. They have the generic formula CnH2n
4. The names end in "-ene"
5. They represent the simplest of the unsaturated hydrocarbons.
6. An alkene has two less hydrogens than an alkane.
ALKENE NOMENCLATURE
1. Find the longest chain with the double bond.
2. Number the chain so the double bond gets the lowest number.
3. Name & number attached groups as you would for alkanes.
4. Parent gets –ene ending; Indicate position of double bond with a number.
ALKENE NOMENCLATURE
Examples
A.
CH2
CH
CH2
1-butene
CH3
ALKENE NOMENCLATURE
B.
CH
CH3
CH
CH3
2-butene
ALKENE
NOMENCLATURE
1,3-butadiene
C.
H
C
H
H
C
C
C
H
H
H
ALKENE NOMENCLATURE
D.
propadiene
CH2
C
CH2
ALKYNES
1. They have a triple covalent bond in the carbon chain
2. They have the generic formula CnH2n-2
3. They have two less hydrogens than alkenes
Alkyne Nomenclature
1. Find the longest chain with the triple bond & number it so the triple
bond has the lowest number.
2. Name and number the attached groups.
3. Parent gets –yne ending; Indicate position of triple bond with a number.
Alkyne Nomenclature
Examples:
A.
CH
C
CH2 CH3
1-butyne
Alkyne
Nomenclature
B.
3,3-dimethyl-1-butyne
CH3
CH
C
C
CH3
CH3
Cyclo-Compounds
1. Sometimes the chains can be circled and the end carbons join together.
2. This brings about the loss of two hydrogen atoms
3. An example is that of the six-carbon hexane forming the six-carbon
cyclohexane which has the formula C6H12
4. You use of the prefix "cyclo-" in front of the parent name, hexane
EXAMPLES
EXAMPLES
AROMATICS
1. The other main group of hydrocarbons is that of the aromatic
hydrocarbons
2. They contain six carbons arranged in a "ring" and contain three double
covalent bonds between every other carbon-carbon pair.
3. The basic aromatic hydrocarbon is benzene, C6H6
4. Ways to represent benzene
Aromatics Nomenclature
1. Monosubstituted name like other hydrocarbons with –benzene as the
parent name.
2. Disubstituted named using prefixes
ortho (1,2)
meta (1,3)
para (1,4)
Aromatics Nomenclature
Br
A.
Br
ortho
1,2-dibromobenzene
Aromatics Nomenclature
o-dibromobenzene
B.
Br
para
1,4-dibromobenzene
Br
Aromatics
Nomenclature
p-dibromobenzene
C. Br
meta
1,3-dibromobenzene
Br
Aromatics
Nomenclature
m-dibromobenzene
D.
CH3
3-ethyl-1-methylbenzene
CH2 CH3
Substituted Hydrocarbons
1. Atoms of other elements can be joined to the carbons in place of one or
more hydrogens.
2. Oxygen, nitrogen, sulfur and the halogens are the most common atoms
that replace hydrogens.
3. The resulting compound is called a substituted hydrocarbon.
4. Sometimes a combination of two of these other elements will be found in
place of hydrogens.
5. These other elements give rise to what are called functional groups.
ALCOHOLS
1. The most common of the functional groups
2. Contains an "- OH" group, which is known as the hydroxyl group
3. An aliphatic hydrocarbon that has one hydroxyl group attached to a
carbon is called an alcohol.
Alcohol Nomenclature
1. Select the longest carbon chain containing –OH group.
2. Replace the -e ending of the parent alkane with -ol
3. Number the alkane chain beginning at the end nearer the –OH group.
4. Number the attached groups according to their position
Alcohol Nomenclature
2-methyl-2-propanol
A.
CH3
CH3
C
CH3
OH
Alcohol Nomenclature
B.
CH3CH2OH
Alcohol
Nomenclature
ethanol
C.
CH3OH
methanol
Alcohol
Nomenclature
D.
H
H
H
2-butanol
H
H
C
C
C
H
H
OH H
C
H
ETHERS
1. Results when there is an oxygen atom between two carbons in the chain
2. Ethers are represented as R-O-R', where R and R' can be the same or
different hydrocarbon units.
Ether Nomenclature
1. Identify the two attached groups and add the word ether.
2. If there are more than 2 attached groups name as a benzene ring.
Ether Nomenclature
A.
CH3CH2
O
CH3
Ethylmethyl
ether
Ether
Nomenclature
Diethyl ether
B.
CH3CH2
O
CH2CH3
Aldehydes
Aldehydes
• These
compounds
show
the arises when an oxygen atom is
1. A new
class of substituted
hydrocarbons
generic
formula,
double bonded
to the carbon at the end of the chain.
2. These compounds show the generic formula,
O
R
C
H
Aldehyde Nomenclature
1. Replace the – e of the parent alkane with –al
2. The longest chain selected includes the aldehyde group.
3. The carbon in the aldehyde group is always numbered as the #1 carbon.
Aldehyde Nomenclature
A.
O
H
C
H
Aldehyde Nomenclature
Methanal
B.
O
CH3
C
H
Ethanal
Ketones
Ketones
•The•generic
formula for ketones
A different class of organic compounds results if the C=O occurs
somewhere along the chain other than on the end carbon
is
•The generic formula for ketones is
O
R
C
R
Ketone Nomenclature
1. Replace the – e of the parent alkane with – one
2. The longest chain selected includes the ketone group.
3. Numbering begins nearer the carbonyl carbon.
Ketone Nomenclature
A.
O
CH3
C
CH3
Ketone
Nomenclature
propanone
B.
O
C
CH3
Carboxylic
Acids
2-butanone
CH2CH3
d a lot in nature formed by
xidation of alcohols and Carboxylic Acids
•Found a lot in nature formed by the oxidation of alcohols and aldehydes.
ydes.
• These compounds show the generic formula,
compounds show the
c formula,
O
R
C
OH
Carboxylic Acid Nomenclature
1. Carboxyl carbon is number one.
2. Parent alkane – e is replaced with – oic acid
Carboxylic Acid Nomenclature
Propanoic Acid
A.
O
CH3
CH2
C
OH
Carboxylic Acid Nomenclature
B.
5-methylhexanoic acid
CH3
O
CH3CCHCH2CH2COH
Polymers
1. Large molecule formed by the covalent bonding of repeating smaller
molecules.
2. Monomer:
Smaller molecules that combine to form the repeating unit of a polymer.
3. Polymerization:
Joining two or more monomers together creating a polymer.
4. First synthetic polymer was nylon (1930s).
5. Two methods synthesizing polymers are addition and condensation
polymerization.
6. Addition:
Unites thousands of monomers into a single enormous molecule
7. Condensation:
Joining of two molecules (monomers) and the elimination of a small
molecule, usually water.