Organic chemistry

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.

In chemistry, the words “organic chemistry” are defined a little more precisely:
Organic chemistry is concerned with the study of the structure and properties of compounds
containing carbon.
– All organic compounds contain carbon atoms.
– Inorganic compounds contain no carbons. Most inorganic compounds are ionic compounds.
- Some carbon compounds are not considered to be organic (mostly for historical reasons), such
as CO, CO2, diamond, graphite, carbonic acid

Origins of Organic Chemistry

• Organic literally means “derived from living organisms”—organic chemistry was originally the
study of compounds extracted from living organisms and their natural products.
• It was believed that only living organisms possessed the “vital force” necessary to create
Organic compounds (“vitalism”).
• This concept started to change in 1828 after Friedrich Wöhler showed that it was possible to
make urea, a known “organic compound” from a mineral source.
• What this and later experiments showed was that “organic” molecules — even those made by
living organisms — can be handled and synthesized just like minerals and metals
• Carbons atoms can be linked by strong, stable covalent bonds.
• Carbon atoms can form stable bonds to many other elements (H, F, Cl, Br, I, O, N, S, P, etc.).
Most organic compounds contain a few hydrogens, and sometimes oxygen, nitrogen, sulfur,
phosphorus, etc.
• Carbon atoms can form complex structures, such as long chains, branched chains, rings,
Chiral compounds (having a particular “handedness”), complex 3D shapes, etc.
• Because of this variety in bonding and complexity, carbon atoms can form a tremendous
variety of compounds. More than 30,000,000 organic compounds are known, as opposed to
 about 600,000 inorganic compounds.
• Complex organic compounds can perform a number of useful biological functions (vitamins,
carbohydrates, lipids, proteins, enzymes, ATP, DNA, RNA are all organic compounds) which
are studied in biochemistry.
• Complex organic compounds are present in the foods we eat (carbohydrates, proteins, fats, etc.)
• Most medicines, whether they come from a chemical plant or a green plant, are organic
compounds.
• Most fuels are organic compounds (wood, coal, natural gas, gasoline, kerosene, diesel fuel, oil,
And other petroleum-based products).
• Complex organic compounds are also useful in technology (paints, plastics, rubber, textiles,
etc.).
Organic vs. Inorganic Compounds
• Organic compounds are held together by covalent bonds, while inorganic compounds are held
together by ionic bonds.

Properties of typical organic and inorganic compounds.

Property Organic Inorganic
Bonding within molecules Usually covalent Often ionic
Forces between molecules Generally weak Quite strong
Normal physical state Gases, liquids, or low Usually high melting-
melting-point solids point solids
Flammability Often flammable Usually nonflammable
Solubility in water Often low Often high
Conductivity of aqueous solutions Nonconductor Conductor

Carbon (C) appears in the second row of the periodic table and has four bonding electrons in its
valence shell (see our Periodic Table module for more information). Similar to other non-metals,
carbon needs eight electrons to satisfy its valence shell. Carbon therefore forms four bonds with
other atoms (each bond consisting of one of carbon's electrons and one of the bonding atom's
electrons). Every valence electron participates in bonding, thus a carbon atom's bonds will be
distributed evenly over the atom's surface. These bonds form a tetrahedron (a pyramid with a spike
at the top), as illustrated below:
Carbon forms 4 bonds

Organic chemicals get their diversity from the many different ways carbon can bond to other
atoms. The simplest organic chemicals, called hydrocarbons, contain only carbon and hydrogen
atoms; the simplest hydrocarbon (called methane) contains a single carbon atom bonded to four
hydrogen atoms:

Methane - a carbon atom bonded to 4 hydrogen atoms

But carbon can bond to other carbon atoms in addition to hydrogen, as illustrated in the
molecule ethane below:

Ethane - a carbon-carbon bond

In fact, the uniqueness of carbon comes from the fact that it can bond to itself in many different
ways. Carbon atoms can form long chains:

Hexane - a 6-carbon chain

branched chains: rings:

Isohexane - a branched-carbon chain Cyclohexane - a ringed hydrocarbon

There appears to be almost no limit to the number of different structures that carbon can form.
To add to the complexity of organic chemistry, neighboring carbon atoms can form double and
triple bonds in addition to single carbon-carbon bonds:

Single bonding
Double bonding Triple bonding

Keep in mind that each carbon atom forms four bonds. As the number of bonds between any two
carbon atoms increases, the number of hydrogen atoms in the molecule decreases.

The simplest hydrocarbons are those that contain only carbon and hydrogen. These simple
hydrocarbons come in three varieties depending on the type of carbon-carbon bonds that occur in
the molecule. Alkanes are the first class of simple hydrocarbons and contain only carbon-carbon
single bonds. The alkanes are named by combining a prefix that describes the number of carbon
atoms in the molecule with the root ending "ane". The names and prefixes for the first ten alkanes
are given in the following table.

Alkanes

Carbon Prefix Alkane Chemical Structural Alkyl

Atoms Name Formula Formula

1 Meth Methane CH 4 CH4 CH3- methyl

2 Eth Ethane C2H6 CH3-CH3 CH3-CH2- ethyl

3 Prop Propane C3H8 CH3-CH2-CH3 CH3-CH2-CH2- propyl

CH3-CH-CH3 izopropyl

4 But Butane C4H10 CH3-CH2-CH2-CH3

5 Pent Pentane C5H12 CH3-(CH2)3-CH3

6 Hex Hexane C6H14 ...

7 Hept Heptane C7H16

8 Oct Octane C8H18

9 Non Nonane C9H20

10 Dec Decane C10H22

Term Definitions
organic compound contains carbon and hydrogen, is often combined with
a few other elements (O,N,S,P, CL,F,Br, I)
hydrocarbon an organic compound that contains only the elements
hydrogen and carbon
isomer compounds with the same chemical formula but
different structural formulas

straight chain when the carbon atoms of a hydrocarbon are arranged

in a straight chain
branched chain when the carbon atoms of a hydrocarbon are arranged
in a branched chain

saturated hydrocarbon a hydrocarbon in which all of the bonds are single

unsaturated hydrocarbon a hydrocarbon that contains one or more double or

triple bonds
alkane a hydrocarbon in which all of the bonds are single

alkene a hydrocarbon that has double bonds

alkyne a hydrocarbon that has triple bond

aromatic hydrocarbon hydrocarbons that have similar ring structures and

carry a strong odor
Write formulas and names of compounds
methane ethene

propyne pent 2-ene

but-1-yne cyclohexane

2-methylpropene 3-ethylpent-2-ene

3-etyl-2-metylpentane 2,2,3,3-tetramethylhexane

2,2-dimetyl-4-propyloktane cyclopentene

CH4 CH3-CH2-CH3

CH2=CH2 CH3-CH2-CH= CH-CH2-CH3

CH3-CH=CH2 CH3-CH2- CH = CH-CH3

.
 Term Definitions
substitution reaction one atom or group replaces another.
CH4 + Cl2 → CH3Cl + HCl often reactions of alkanes, alkyl halides, and aromatic
+ UV
compounds

addition reaction all parts of the adding reagent appear in the product
CH2=CH2 + H2  CH3- CH3 characteristic of compounds with multiple bonds

elimination reaction one molecule loses a smaller molecule

CH3- CH3  CH2=CH2 + H2 method of preparing compounds with double and triple
bonds
rearrangement reaction reorganization of the molecule's atoms
butane  2-methylpropane konstitutional isomers

reduction increasing the hydrogen content or decreasing the

CH3- CHO  CH3-CH2-OH oxygen content

oxidation decreasing the hydrogen content or increasing the

CH4 + 2O2 → CO2 + 2H2O oxygen content

two ways to break a covalent bond heterolytic cleavage and homolytic cleavage

homolysis (homolytic cleavage) breaking a bond by equally dividing the electrons

Cl2 → Cl. + Cl. between 2 atoms in the bond
produces radicals - have an unpaired electron
heterolysis (heterolytic cleavage) breaking a bond by unequally dividing the electrons
HCl → H+ + Cl- between 2 atoms in the bond
produces ions
electrophile seeking negative charges -
H+, NO2+
nucleophile seeking positive charges +
Cl-, OH-

Determine the type of reaction

CH4 + Cl2  CH3-Cl + HCl

CH2 =CH2 + Cl2  CH2Cl-CH2Cl

 CH3-CH3  CH2 =CH2 + H2

CH4 + 2O2  CO2 + 2H2O

CH2 =CH2 + HCl  CH3-CH2-Cl

C6H12 → C6H6 + 3H2