Vital Force Theory - The idea that organic compounds could only originate from living

material.

Resonance Forms - Lewis Structures that differ only in location of electrons are resonance
forms.

Formal Charge = group # – # lone pair e– – # bonds

Covalent Bond - Overlap of atomic orbitals (AO’s)

Hybridization - A mixing of AO’s which produces hybrid orbitals of equal energy but hybrid
character.

Geometric Isomers - Structural isomers that differ only in the spatial orientation of substituent
groups.

Cis - Indicates that substituent groups are oriented together or on the same side of a rigid
molecule.

Trans - Indicates that substituent groups are oriented opposed or on opposite sides of a rigid
molecule.
–
Nucleophile - “nucleus loving”, electron pair source, Nu: ex. NH3, HO , H2O

Electrophile - “electron loving” nucleus source, El+ ex. H+, Br+

Radical - Species with an unpaired electron – neutral, R•

Reaction mechanism intermediate - Relatively stable high - energy species formed during
the course of a reaction.

Leaving group (nucleofuge) - An atom or group of atoms that leave a molecule with an
electron pair. ex. I, Br, Cl, OH, etc.

Classification of Organic Reactions

SN1 Unimolecular nucleophilic substitution
SN2 Bimolecular nucleophilic substitution
E1 Unimolecular elimination
E2 Bimolecular elimination
R Radical chain reaction

Transition state (activated complex) - The particular arrangement of reactant and product
molecules at a point of maximum energy along the reaction coordinate.

Homologous series - A series of compounds in which each subsequent member of the series
contains one more - CH2 - group than the previous member.
Substituent - An atom or group of atoms attached to a larger chain or ring of atoms.
(Substitute for “H”)

Alkyl Group - A substituent derived from an alkane. Similar to R - group. Named by adding -
yl to root name.

Primary (1°) Carbon - Carbon atom with one other carbon attached. (3 hydrogen atoms)
Secondary (2°) Carbon - Carbon atom with two other carbons attached. (2 hydrogen atoms)
Tertiary (3°) Carbon - Carbon atom with three other carbons attached. (1 hydrogen atom)
Quaternary (4°) Carbon - Carbon atom with four other carbons attached. (0 hydrogen atoms)

Hydrocarbons - Compounds that consist solely of carbon and hydrogen.

Saturated Hydrocarbons - Compounds that contain the maximum possible number of

hydrogen atoms. Ex. alkanes.

Unsaturated Hydrocarbons - Compounds that contain double and/or triple bonds. Ex.
alkenes and alkynes.

Aliphatic Hydrocarbons - Alkanes, alkenes and alkynes and their cyclic derivatives.

Aromatic Hydrocarbons - A special class of organic compound that contains 4n+2

conjugated p - electrons in a ring where n = any whole number. The parent aromatic
hydrocarbon is benzene (n = 1).

Zaitsev's Rule - The product that contains the most substituted trans - double bond is
favored.

Oxidation - Loss of electrons. (Leo) Loss of two hydrogen atoms or the gain of an oxygen
atom.

Reduction - Gain of electrons. (Ger) Gain of two hydrogen atoms or loss of an oxygen atom.

Condensation - A combination reaction between two small molecules to form a larger

molecule.

Stereoisomers - Any of a group of isomers in which atoms are linked in the same order but
differ in their spatial arrangement. (cis/trans isomers)

Plane - polarized light - Light that is oscillating between electronic and magnetic properties in
only one plane in space.

Optical isomers - Isomers that rotate plane - polarized light in opposite directions.

Polarimeter - A scientific instrument used to measure optical rotation of plane polarized light.
Specific Rotation, [α] - The number of degrees that polarized light would be rotated by
passage through 1 decimeter (dm or 10 cm) of a solution at a concentration of 1.00 g/ml.

Optical Activity - Any substance that rotates plane-polarized light is optically active.

Dextrorotatory (+) - Observed rotation of the substance is clockwise or right.

Levorotatory (–) - Observed rotation of the substance is counter clockwise or left.

Symmetry - Correspondence in size, shape, and relative position of parts on opposite sides of
a dividing line or median plane or about a center or axis.

Asymmetry - The absence of all symmetry elements. All asymmetric objects are chiral.

Symmetry element - A plane, line or point in or through an object, about which a rotation or
reflection leaves the object in an orientation indistinguishable from the original.

Superimpose - To place or lay over or above something.

Asymmetric Carbon - Any carbon atom with four different groups attached. An asymmetric
carbon atom.

Configuration - The three - dimensional arrangement of atoms in a molecule in space.

Plane of Symmetry - (σ - plane) An imaginary plane or line which bisects an object so that
one half is the mirror image of the other half.

Chirality - The property of an object that is not identical with it’s mirror images. Objects that
are not superimposable with their mirror images. Objects without a plane of symmetry.
Examples: hands, shoes, gloves etc.

Chiral - A material that exhibits chirality.

Achiral - Objects that are identical with their mirror images. Objects that are superimposable
with their mirror images. Objects with a plane of symmetry.

Chiral or stereogenic center - The center of asymmetry in a chiral molecule. Usually a

carbon atom with four different attachments.

Enantiomers - Molecules that are not superimposable on their mirror images. Every chiral
molecule has a pair of enantiomers.

Racemic Mixture - A 50:50 mixture of enantiomers. A racemic mixture has a specific rotation
of 0°.
Scalemic Mixture - Any mixture other than a 50:50 mixture of enantiomers and having a
specific rotation of greater or less than zero.

Diastereomers - Stereoisomers that are not enantiomers.

Meso Compound - A molecule with two or more chiral carbons but is superimposable on its
mirror image. (ie. has a plane of symmetry), [α]D = 0°

Carbohydrates - Polyhydroxy aldehydes or ketones and compounds that yield these

compounds when hydrolyzed.