Organic Chemistry

Aliphatic
Term applied to compounds that do not contain benzene or benzene-like rings as structural units.
Aromatic
An electron-delocalized species that is much more stable than any structure written for it in which all the electrons are localized either in covalent bonds or as unshared electron pairs.
Alkanes
Hydrocarbon in which all the bonds are single bonds. These have the general formula CnH(2n+2)
Alkenes
Hydrocarbon that contains a carbon-carbon double bond (C=C); also known by the older name olefin.
Alkynes
Hydrocarbon that contains a carbon-carbon triple bond.
Valence bond model
bases the connection between two atoms on the overlap between half-filled orbitals of the two atoms
Molecular orbital model
assembles a set of molecular orbitals by combining the atomic orbitals of all of the atoms in the molecule
Sigma bond
a bond along the internuclear axis
Bonding orbital

Nonbonding orbital

lower energy, sigma or pi

higher energy, sigma* or pi*

Methane
simplest alkane, most abundant
Ethane
second most abundant alkane
Propane
third most abundant alkane
sp3 hybridization
A model to describe the bonding of a carbon attached to four other atoms or groups. The carbon 2s orbital and the three 2p orbitals having 25% s character and 75% p character. These orbitals are directed toward the corners of a tetrahedron.
Methyl
CH3
n-butane
“normal” therefore unbranched, isomer of C4H10
isobutane
isomer of C4H10, has a branched chain
Methylene groups

Methine groups

CH2

CH

n-Alkanes
“normal” alkanes, unbranched
n-Pentane
has a chain 5 carbons
n-Hexane
has a chain of 6 carbons
Homologous series
Group of structurally related substances in which successive members differ by a CH2 group.
Primary carbon
A carbon that is attached to only one other carbon.
Secondary carbon
A carbon that is directly attached to two other carbons.
Tertiary
A carbon that is directly attached to three other carbons.
Quarternary
A carbon that is directly bonded to four other carbons
Cracking
A key step in petroleum refining in which high-molecular-weight hydrocarbons are converted to lower molecular-weight ones by thermal or catalytic carbon-carbon bond cleavage.
Reforming
Step in oil refining in which the proportion of aromatic and branched-chain hydrocarbons in petroleum is inceased so as to improve the octane rating of gasoline.
Intermolecular attractive forces
Forces between two atoms or groups in SEPARATE molecules.
van der Waals forces
Intermolecular forces that do no involve ions (dipole-dipole, dipole/induced dipole, and induced dipole/induced dipole forces)
Induced dipole
Force of attraction resulting from a mutual and complementary polarization of one molecule by another. Also referred to as London forces or dispersion forces.
van der Waals radius
A measure of the effective size of an atom or a group. The repulsive forces between two atoms increases rapidly when they approach each other at distances less than the sum of their van der Waals radii.
Hydrophobic effect
Exclusion of nonpolar molecules from water (like dissolves in like)
Parrafin hydrocarbons
An old name for alkanes and cycloalkanes
Combustion
Burning of a substance in the presence of oxygen. All hydrocarbons yield carbon dioxide and water when they undergo combustion,
Heat of combustion
Heat evolved on combustion of a substance. It is the value of -deltaH for the combustion reaction.
Enthalpy
The heat content of a substance; H.
Potential energy
The energy a system has exclusive of its kinetic energy.
Intramolecular forces
Forces between two atoms or groups WITHIN the same molecule.
Oxidation number
The formal charge an atom has when the atoms in its covalent bonds are assigned to the more electronegative partner.
sp2 hybridization
A model to describe the bonding of a carbon attached to three other atoms or groups. The carbon 2s orbital and the two 2p orbitals are combined to give a set of three equivalent _____ orbitals having 33.3% s character and 66.7% p character. One p orbital remains unhybridized. A trigonal planar geometry is characteristic of _____ hybridization.
Pi bond
The bond between the left over unhybridized p orbital on carbon; above and below the internuclear axis; in double and triple bonds.
Pi electrons
Probability of their location is highest above and below the internuclear axis
sp hybridization
Hybridization state adopted by carbon when it bonds to two other atoms as, for example, in alkynes. The s orbital and one of the 2p orbitals mix to form two equivalent ____-hybridized orbitals. A linear geometry is characteristic of ____ hybridization.
1 carbon
methane
2 carbons
Ethane
2 carbons
Ethane
5 carbons
pentane
3 carbons
propane
4 carbons
butane
6 carbons
hexane
7 carbons
heptane
8 carbons
octane
9 carbons
nonane
10 carbons
decane
10 carbons
decane
11 carbons
undecane
12 carbons
dodecane
13 carbons
tridecane
14 carbons
tetradecane
15 carbons
pentadecane
16 carbons
hexadecane
17 carbons
heptadecane
18 carbons
octadecane
19 carbons
nonadecane
20 carbons
icosane
21 carbons
henicosane
22 carbons
docosane
23 carbons
tricosane
24 carbons
tetracosane
30 carbons
triacontane
31 carbons
hentriacontane
32 carbons
dotriacontane
40 carbons
tetracontane
50 carbons
pentacontane
100 carbons
hectane
x

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