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Organic Chemistry McMurry 7th
Chapter 1 Terms
37
Chemistry
Undergraduate 3
08/17/2008

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Term
Organic chemistry
Definition
the study of carbon compounds
Term
atomic number (Z)
Definition
the number of protons in the nucleus of an atom
Term
mass number (A)
Definition
the total of protons plus neutrons
Term
isotopes
Definition
atoms of the same element that have different mass numbers
Term
atomic weight
Definition
the average mass number of the atoms of an element
Term
orbital (Ψ)
Definition
a wave function, which describes the volume of space around a nucleus in which an electron is most likely found
Term
node
Definition
a surface of zero electron density within an orbital
Term
ground-state electron configuration
Definition
the most stable, lowest energy electron configuration of a molecule or atom
Term
electron configuration rules
Definition
1) the lowest energy orbitals fill first, according to the order 1s->2s->2p->3s->3p->4s->3d, a statement called the aufbau principle; 2) electrons act as if they were spinning around an axis, in much the same way that the earth spins. This spin can have two orientations, denoted as up and down arrows; only two electrons can occupy an orbital, and they must be of opposite spin, a statement called the Pauli exclusion principle; 3) if two or more empty orbitals of equal energy are available, one electron occupies each with spins parallel until all orbitals are half full,a statement called Hund's rule
Term
s orbital
Definition

spherical shape; one per shell

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Term
p orbital
Definition

dumbell shaped; three mutually perpendicular per shell, denoted as px, py, pz

[image]

Term
d orbital
Definition

4 of 5 are cloverleaf shaped and the fifth is an elongated dumbell shape with a donut around the middle; five per shell

[image]

Term
electron shells
Definition
the layers in which the orbitals of an atom are organized into; they become progressively larger and higher in energy the further from the atom they are
Term
valence shell
Definition
the outermost shell of an atom
Term
covalent bond
Definition
a shared-electron bond between atoms
Term
molecule
Definition
the neutral collection of atoms held together by covalent bonds
Term
electron-dot structures
Definition
aka Lewis structures; a way of representing the valence electrons of an atom as dots
Term
line-bond structures
Definition
aka Kekule structures; a two-electron covalent bond is indicated as a line drawn between atoms
Term
lone-pair electrons/nonbonding electrons
Definition
valence electrons that are not used for bonding
Term
valence bond theory
Definition

when two atoms approach each other closely and a singly occupied orbital on one atom overlaps a singly occupied orbital on the other atom, a covalent bond forms between the two atoms

ex., H-H bond

[image]

Term
sigma (s) bonds
Definition
a covalent bond formed by head-on overlap of atomic orbitals
Term
bond strength
Definition
an alternative name for bond dissociation energy (the energy required to break a bond)
Term
bond length
Definition
the equilibrium distance between the nuclei of two atoms that are bonded to each other
Term
sp3 hybrid orbital
Definition
a hybrid orbital derived by combination of an s atomic orbital with three p atomic orbitals; the four orbitals that result are directed toward the corners
 of a regular tetrahedron at angles of 109° to each other; they form stronger bonds than regular s or p orbitals
Term
bond angle
Definition

the angle formed between two adjecent bonds; e.g., the tetrahedral orientation of methane (CH4) where each H is 109.5° from the other

 

Term
tetrahedral sp3 orbitals
Definition

contain 109.5° angles, e.g., methane

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Term
trigonal sp2 orbitals
Definition

120° angles between orbitals

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Term
sp2 hybrid orbitals
Definition
a hybrid orbital derived by combination of an s atomic orbital with 2 p atomic orbitals; the three orbitals that result lie in a plane at angles of 120° to each other, and the other p orbital remains unchanged; shown as double bonds
Term
pi (p) bond
Definition
the covalent bond formed by sideways overlap of atomic orbitals; e.g., carbon-carbon double bonds
Term
sp hybrid orbital
Definition
a hybrid orbital derived from the combination of an s and a p atomic orbital; the two orbitals that result are oriented at an angle of 180° to each other and the remaining two p orbitals are left unchanged; shown as triple bonds
Term
linear sp bond
Definition

180° angles; e.g., acetylene

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Term
molecular orbital (MO) theory
Definition
a description of covalent bond formation as resulting from a mathematical combination of atomic orbitals (wave functions) to form molecular orbitals
Term
bonding MO
Definition
a molecular orbital that is lower in energy than the atomic orbitals from which it is formed
Term
antibonding MO
Definition
a molecular orbital that is higher in energy than the atomic orbitals from which it is formed
Term
condensed structure
Definition
a shorthand way of writing structures in which carbon-hydrogen and carbon-carbon bonds are understood rather than shown explicitly; e.g., propane = CH3CH2CH3
Term
skeletal structures
Definition

a shorthand way of writing structures in which carbon atoms are assumed to be at each intersection of two lines (bonds) and at the end of each line; e.g., phenol, C6H6O

[image]

Term
rules for drawing skeletal structures
Definition
1) carbon atoms aren't shown but are assumed to be at each intersection and at the end of lines; 2) hydrogen bonded to carbon is not shown - carbon always has a valence of 4, thus the hydrogens are known to be there; 3) atoms other than H and C are shown
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