Organic Chemistry

What Do We Mean By
“Organic”?
• In everyday usage, the word organic can be found in several
different contexts:

– chemicals extracted from plants and animals were originally

called “organic” because they came from living organisms.
– organic fertilizers are obtained from living organisms.
– organic foods are foods grown without the use of pesticides or
synthetic fertilizers.
 Brief History of Organic
Chemistry
Organic matter could only be produced in a living organism,
vitalists argued, because the organism had a vital force that
is not present in laboratory chemicals. Then, in 1828, a
German chemist named Friedrich Wöhler decomposed a
chemical that was not organic to produce urea (N2H4CO),
a known organic compound that occurs in urine. Wöhler’s
production of an organic compound was soon followed by
the production of other organic substances by other
chemists.
 What is Organic Chemistry?
• Organic chemistry is the study of carbon compounds.
– Organic compounds have carbon AND hydrogen
– Carbon Dioxide is NOT organic

• The versatility and stability of carbon’s molecular

structures provides the enormous range of properties of its
compounds.

• Carbon can bond to other carbons

– Reason for the degree of structural complexity
Organic Chemistry in Everyday Life

•Smells & tastes: fruits, fish, mint

•Medications: aspirin, Tylenol, decongestants, sedatives, insulin
•Addictive substances: caffeine, nicotine, alcohol, narcotics
•Hormones/Neurotransmitters: adrenaline, dopamine, serotonin
•Food: carbohydrates, protein, fat, vitamins
•Genetics: DNA, RNA
•Consumer products: plastics, nylon, rayon, polyester
 Organic Chemistry
• Carbon
– Has 4 valence electrons
– Makes 4 covalent bonds to fill its octet
• Can include double and triple bonds

– Hydrocarbon
• Compound with only carbon and hydrogen
 Saturation
• Saturated: a carbon chain contains as many
hydrogens as possible.
• Saturated compounds contain only single C-H
bonds. Alkanes are saturated.

• Unsaturated means that a carbon chain

contains at least one multiple (double or
triple) bond.
– Alkene = double bond
– Alkyne = triple bond
 HYDROCARBONS
A hydrocarbon is an organic compound consisting of only two
elements. As the name implies, these elements are hydrogen and
carbon. The simplest hydrocarbon has one carbon atom and four
hydrogen atoms but since carbon atoms can combine with one
another, there are thousands of possible structures and arrangements.
The carbon-to-carbon bonds are covalent and can be single, double, or
triple.

To satisfy the octet rule, this means that each carbon atom must have a
total of four dashes around it, no more and no less. Note that when the
carbon atom has double or triple bonds, fewer hydrogen atoms can be
attached as the octet rule is satisfied. There are four groups of
hydrocarbons that are classified according to how the carbon atoms
are put together: (1) alkanes, (2) alkenes, (3) alkynes, and (4)
aromatic hydrocarbons.
 Alkanes
The alkanes are hydrocarbons with single covalent bonds
between the carbon atoms. Alkanes that are large enough
to form chains of carbon atoms occur with a straight
structure, a branched structure, or a ring structure.
 1-meth 6-hex
Alkane
Single bonds 2-eth 7-hept
CnH2n+2
Ends in -ane 3-prop 8-oct
H H
Ex. H- C- C- H 4-but 9-non
C2H6 H H

5-pent 10-dec
Saturated
All single bonds--- ALKANES ONLY!!
A molecular formula (A) describes
the numbers of different kinds of
atoms in a molecule.

(B) A structural formula

represents a two-dimensional
model of how the atoms are
bonded to one another. Each dash
represents a bonding pair of
electrons.
 Hydrocarbons
IUPAC Molecular Condensed Boiling
name
. Formula Formula Point (°C)
Methane CH4 CH4 -161.5
Ethane C2 H 6 CH3CH3 -88.6
Propane C3 H 8 CH3CH2CH3 -42.1
Butane C4H10 CH3(CH2)2CH3 -0.5
Pentane C5H12 CH3(CH2)3CH3 36.1
Hexane C6H14 CH3(CH2)4CH3 68.7
Heptane C7H16 CH3(CH2)5CH3 98.4
Octane C8H18 CH3(CH2)6CH3 125.7
Nonane C9H20 CH3(CH2)7CH3 150.8
Decane C10H22 CH3(CH2)8CH3 174.1
 Structure and Physical Properties

Methane Ethane Propane Butane

16 g/mol 30 g/mol 44 g/mol 58 g/mol
-161.5oC -88.6oC -42.1oC -0.5oC

• Larger molar mass = higher boiling point

– Bigger compound – higher boiling point
 Petrochemicals
• Simple, small hydrocarbons are
petrochemicals
– Chemicals isolated from crude oil (petroleum)
• Octane – used in gasoline
• Propane – used in grills, heaters, etc.
• Butane – lighter fluid
Isomers
Compounds with the same molecular formulas with different
structures are called isomers. Example, the straight-chained isomer
is called n-butane, the branched isomer is called isobutane. The
isomers of a particular alkane, such as butane, have different physical
and chemical properties because they have different structures.
 Steps:
Find longest chain of carbons, circle it
Name the longest chain of carbons
Look for double/triple bonds (tell where they are)
Look for branches, name, & tell where they are
Ex.
Ex. #2

H H H H CH3-CH2-CH2-CH-CH2-CH3
H-C- C- C- C- H
H H H H CH3
3-methyl hexane
Butane
Draw all possible structures having the formulas:

C5H12
C6H14
Methane, ethane, and propane can have only one
struc ture each, and butane has two isomers. The
number of possible isomers for a particular
molecular formula increases rapidly as the
number of carbon atoms increases. After butane,
hexane has 5 isomers, octane 18 isomers, and
decane 75 isomers. Because they have different
structures, each isomer has different physical
properties.
ALKENES
The alkenes are hydrocarbons with a double covalent carbon-to
carbon bond. To denote the presence of a double bond, the -ene
suffix in alkene is added.

Alkenes have room for two fewer hydro gen atoms because of the
double bond, so the general alkene formula is CnH2n. Note the
simplest alkene is called ethene but is commonly known as
ethylene.
Naming Alkenes – add the suffix -ene
Prefix

1-meth 2-eth 3-prop 4-but 5-pent

6-hex 7-hept 8-oct 9-non 10-dec

Alkynes
Hydrocarbons that have a triple bond between two
carbon atoms are called alkynes. Imagine that two
hydrogen atoms have been removed from each of two
adjacent carbon atoms in an alkane, thereby allowing
these C atoms to form two additional bonds between
them. The general formula for the alkyne series is
CnH2n–2. The simplest alkyne is ethyne, C2H2, more
commonly called acetylene.
Naming Alkynes – add the suffix -yne
Prefix

1-meth 2-eth 3-prop 4-but 5-pent

6-hex 7-hept 8-oct 9-non 10-dec

CYCLOALKANES AND AROMATIC HYDROCARBONS
Carbon atoms can also bond to one another to form a ring, or cyclic,
structure. Note that the cycloalkanes have the same molecular
formulas as the alkenes; thus, they are isomers of the alkenes. This
shows the importance of structural, rather than simply molecular,
formulas in referring to organic compounds.
CYCLOALKANES AND AROMATIC HYDROCARBONS
Organic compounds that are based on the benzene ring
structure are called aromatic hydrocarbons.
 Functional Groups
• Functional
Group –
group of
atoms which
control how
the molecule
reacts

Organic compounds that contain elements other than carbon and hydrogen are
called derivatives of hydrocarbons.
Alkyl Halides
The general formula for an alkyl
halide is R----X, or just RX, where X
is a halogen atom and R is an alkyl
group.
 Alcohols R-OH
An alcohol is an organic compound formed by replacing one
or more hydrogens on an alkane with a hydroxyl functional
group (–OH). It remains attached to a hydrocarbon group
(R), giving the compound its set of properties that are
associated with alcohols.

An alcohol with two hydroxyl groups per molecule is called

a glycol. An alcohol with three hydroxyl groups per
molecule is called glycerol (or glycerin).
1-meth 6-hex

2-eth 7-hept

3-prop 8-oct

4-but 9-non

5-pent 10-dec
 ETHERS R-O-R’
Ethers are a class of organic compounds that contain an oxygen
between two alkyl groups. They have the formula R-O-R', with R's
being the alkyl groups. these compounds are used in dye, perfumes,
oils, waxes and industrial use. Ethers are named as alkoxyalkanes.

ethyl methyl ether or methoxyethane

CH3-CH2-O-CH3
 To do so the common alkoxy substituents are given names
derived from their alkyl component (below):
Name the following ethers:

CH3-CH2-O-CH2-CH3 diethyl ether

2-ethoxy-2-methyl-1-propane

2-methoxyheptane
 ethoxyethane

3-ethoxy-5-chlorohexane
 Aldehyde vs. Ketone
An aldehyde is an organic compound in which the
carbonyl group is attached to a carbon atom at the
end of a carbon chain. A ketone is an organic
compound in which the carbonyl group is attached to
a carbon atom within the carbon chain.
Naming Simple Aldehydes and Ketones
Aldehydes are named by finding the longest
continuous chain that contains the carbonyl group.
Change the -e at the end of the name of the alkane
to -al.
 Natural Polymers

Proteins RNA
 Natural Polymers

Polysaccharides
DNA
 Pharmaceuticals
• Most pharmaceuticals are complex, organic
molecules
• Can be natural or manmade

aspirin penicillin Acetaminophen

(aka Tylenol)
 Terms To Know
• Hydrocarbon
• Alkane
• Alkene
• Alkyne
• Saturated
• Unsaturated
• Petrochemicals
• Functional Group
• Polymers
 Skills To Master
• Differentiating alkanes, alkenes, and alkynes
• Differentiating saturated and unsaturated
compounds
• Differentiating natural polymers and
manmade polymers
• Recognizing common pharmaceuticals