Organic Chemistry

The columns of the periodic table are called groups. Members of the same group in the table
have the same number of electrons in the outermost shells of their atoms and form bonds of the same
type.

The horizontal rows are called periods.

 Within the shells, electrons are further grouped into subshells of four different types, identified
as s, p, d, and f in order of increasing energy.

s= 2

p= 6

d= 10

f= 14

an electron in the outer shell associated with an atom, and that can participate in the
formation of a chemical bond if the outer shell is not closed.

Electron Configuration
Electronegativity

- describes the tendency of an atom or a functional group to attract electrons toward itself.
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

Bonding Properties of Carbon

• Carbon forms covalent bonds in all its elemental forms and compounds.

– The ground state electron configuration of C is [He]2s22p2; the formation of carbon ions
is therefore energetically unfavorable.

– C has an electronegativity of 2.5, which is midway between that of most metals and
nonmetals. C prefers to share electrons.

• Carbon exhibits catenation, the ability to bond to itself and form stable chain, ring, and
branched compounds.

– The small size of the C atom allows it to form short, strong bonds.

– The tetrahedral shape of the C atom allows catenation.

Carbon Skeletons

• Each C atom can form a maximum of 4 bonds.

• Groups joined by a single bond can rotate, so there are often several different arrangements of
a given carbon skeleton that are equivalent:

Drawing Carbon Skeletons

Each C atom can form a maximum of four bonds.

These may be four single bonds, OR one double and two single bonds, OR one triple and one single
bond.

The arrangement of C atoms determines the skeleton, so a straight chain and a bent chain represent the
same skeleton.
Groups joined by a single bond can rotate freely, so a branch pointing down is the same as one point up.

Alkanes

Hydrocarbons contain only C and H.

Alkanes are hydrocarbons that contain only single bonds and are referred to as saturated hydrocarbons.

The general formula for an alkane is CnH2n+2, where n is any positive integer.

Alkanes comprise a homologous series, a group of compounds in which each member differs from the
next by a –CH2– group.

Naming Organic Compounds

The name of any organic compound is comprised of three portions:

PREFIX + ROOT + SUFFIX

The root name of the compound is determined from the number of C atoms in the longest continuous
chain.

The suffix indicates the type of organic compound, and is placed after the root.

The suffix for an alkane is –ane.

The prefix identifies any groups attached to the main chain.

Constitutional Isomers

Constitutional or structural isomers have the same molecular formula but a different arrangement of
the bonded atoms.

A straight-chain alkane may have many branched structural isomers.

Structural isomers are different compounds and have different properties.

If the isomers contain the same functional groups, their properties will still be similar.

Alkenes

A hydrocarbon that contains at least one C=C bond is called an alkene.

Alkenes are unsaturated and have the general formula CnH2n.

To name an alkene, the root name is determined by the number of C atoms in the longest chain that
also contains the double bond.

The C chain is numbered from the end closest to the double bond.

The suffix for alkenes is –ene.

Geometric Isomers

The double bond of an alkene restricts rotation, so that the relative positions of the atoms attached to
the double bond are fixed.

Alkenes may exist as geometric or cis-trans isomers, which differ in the orientation of the groups
attached to the double bond.

Geometric isomers have different physical properties.

Alkynes

An alkyne is a hydrocarbon that contains at least one CΞC triple bond.

Alkynes have the general formula CnH2n-2 and they are also considred unsaturated carbons.

Alkynes are named in the same way as alkenes, using the suffix –yne.

Functional Groups

Organic compounds are classified according to their functional groups, a group of atoms bonded in a
particular way.

The functional groups in a compound determine both its physical properties and its chemical reactivity.

Functional groups affect the polarity of a compound, and therefore determine the intermolecular forces
it exhibits.

Functional groups define the regions of high and low electron density in a compound, thus determining
its reactivity.
Alcohols

The alcohol functional group consists of a carbon bonded to an –OH group.

Alcohols are named by replacing the –e at the end of the parent hydrocarbon name with the suffix –ol.

Alcohols have high melting and boiling points since they can form hydrogen bonds between their
molecules.

Haloalkanes

Haloalkanes or alkyl halides contain a halogen atom bonded to carbon.

Haloalkanes are named by identifying the halogen with a prefix on the hydrocarbon name. The C bearing
the halogen must be numbered.

Amines

The amine functional group contains a N atom.

The systematic name for an amine is formed by dropping the final –e of the alkane and adding the suffix
–amine.

Common names that use the name of the alkyl group followed by the suffix –amine are also widely
used.

Alkenes

Alkenes contain the C=C double bond:

Alkenes typically undergo addition reactions.

The electron-rich double bond is readily attracted to the partially positive H atoms of H3O+ ions and
hydrohalic acids.

Aromatic Hydrocarbons

Benzene is an aromatic hydrocarbon and is a resonance hybrid. Its p bond electrons are delocalized.

Aromatic compounds are unusually stable and although they contain double bonds they undergo
substitution rather than addition reactions.
Aldehydes and Ketones

Aldehydes and ketones both contain the carbonyl group, C=O.

Aldehydes are named by replacing the final –e of the alkane name with the suffix –al.

Ketones have the suffix –one and the position of the carbonyl must always be indicated.

Carboxylic Acids

Carboxylic acids contain the functional group –COOH

Carboxylic acids are named by replacing the –e of the alkane with the suffix –oic acid.

Carboxylic acids are weak acids in water, and react with strong bases:

Esters

The ester group is formed by the reaction of an alcohol and a carboxylic acid.

Ester groups occur commonly in lipids, which are formed by the esterification of fatty acids.

Ester hydrolysis can be carried out using either aqueous acid or aqueous base. When base is used the
process is called saponification.

This is the process used to make soaps from lipids.

Amides

An amide contains the functional group:

Amides, like esters, can be hydrolyzed to give a carboxylic acid and an amine.

The peptide bond, which links amino acids in a protein, is an amide group.

The structural hierarchy of proteins.

The double helix of DNA and a section showing base pairs.

Key stages in protein synthesis.

Key stages in DNA replication.