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SI Fundamental Units
Mass
Length
Time
Temperature
Amount of substance
Electric current
Luminous intensity
Kilogram (kg)
Meter (m)
Second (s)
Kelvin (K)
Mole (mol)
Ampere (A)
Candela (cd)
Polyatomic Ions
+
NH4
CN
O2 2
HSO4
CO3
PO4 3
OH
Solution Colors
Exceptions
None
None
Ag+ , Hg2 2+ , Pb2+
Ag+ , Hg2 2+ , Pb2+
Ag+ , Hg2 2+ , Pb2+
Sr2+ , Ba2+ , Hg2 2+ , Pb2+
Exceptions
NH4 + , alkali metal cations, Ca2+ ,
Sr2+ , Ba2+
NH4 + , alkali metal cations
NH4 + , alkali metal cations
NH4 + , alkali metal cations, Ca2+ ,
Sr2+ , Ba2+
Strong Bases
Alkali metal hydroxides
Ca(OH)2
Sr(OH)2
Activity Series
OH
C2 O4 2
CNO
C2 H 3 O 2
hydroxide
oxalate
cyanate
acetate
SCN
SO3 2
CO3 2
PO4 3
S2 O3 2
ammonium
cyanide
peroxide
hydrogen sulfate
thiocyanate
sulfite
carbonate
phosphate
thiosulfate
NO3
ClO4
ClO3
ClO
HPO4 2
CrO4 2
Cr2 O7 2
MnO4
N3
C4 H4 O6 2
O2
PO2 3
SiO3 2
chromate
dichromate
permanganate
azide
tartrate
superoxide
hypophosphite
silicate
H 3 O+
PO3 3
Hg2 2
C2 2
S2 2
AsO3 3
AsO4 3
P2 O7 4
nitrate
perchlorate
chlorate
hypochlorite
hydrogen
phosphate
hydronium
phosphite
mercury (I)
carbide
Phase Changes
disulfide
From solid
arsenite
To solid
arsenate
To liquid melting
pyrophosphate To gas
sublimation
Flame Colors
Calcium
Copper (I)
Copper (II)
Potassium
Lithium
Sodium
Strontium
Barium
Iron (III)
Cesium
Indium
Lead
Rubidium
Blue
Green
Purple
Yellow
Orange
Light blue
Rusty yellow
Thermodynamic Laws
First Law: Energy cannot be created nor destroyed. It
can only be transferred in the form of either heat or work.
Second Law: Any spontaneous reaction increases the entropy of the universe.
Third Law: An ideal solid crystal at 0 K has an entropy
of 0.
Thermodynamic Formulas
Copper (II)
Nickel
Permanganate
Chromate
Dichromate
Iron (II)
Iron (III)
Brick red
Blue
Green or blue-green
Lilac
Dark red
Bright yellow
Red
Light green
Gold
BlueViolet
Blue
Blue
RedViolet
Constants
From gas
deposition
condensation
-
Energy of a quantum
E = h
Wavelength-frequency relationship
c=
Probability distribution
PV =
|(x, y, z)|2 dxdydz
V
Hunds Rule
Atomic size
Ionic size
Quantum Numbers of e
Principal (n)
Azimuthal (l)
Magnetic (ml )
Spin (ms )
Molecular Geometry
Hybridization
sp
sp
sp3
sp d
sp3 d2
Atomic Properties
x p
h/2
Nonbonding
electrons
Geometry
1
the
2
Periodic Properties
Property
Atomic size
Ionization energy
Electron anity
Metallic character
Left to Right
Decreasing
Increasing
Large if adding
to a previously
empty orbital
Decreasing
Top to Bottom
Increasing
Decreasing
No
apparent
change
Increasing
linear
0
1
trigonal planar
bent
Ionic
Electrostatic interactions
0
1
2
tetrahedral
trigonal pyramidal
bent
Metallic
Metallic bonds
0
1
2
3
trigonal bipyramidal
seesaw
T-shaped
linear
0
1
2
octahedral
square pyramidal
square planar
Properties
Soft, low melting
point, poor conduction
Very hard, high
melting point, poor
conduction
Hard, high melting
point, poor conduction
Soft to very hard,
low to very high
melting point, excellent conduction
London
dispersion
force (van der Waals
forces, induced dipoledipole interactions)
Dipole-dipole
tions
interac-
Hydrogen bonds
Acid-Base Theories
Arrhenius
BrnstedLowry
Proton
donors
Proton
acceptors
Hydrogen
atom
Acids
[H+ ] >[OH ]
Bases
[OH ] >[H+ ]
Acids have
H+
Bases have
OH
Unshared
electron pair
Acid + Base
Salt + H2 O
Conjugate
acid
+
Conjugate
base
Lewis
Electron
acceptors
Electron
donors
Electron
accepting
atom
Unshared
electron
pair
Properties of Solutions
Solvation The uniform dispersion of a solute in a solvent.
Hydration
Solvation in water.
Crystallization
The reverse reaction of solvation.
Saturated
A solution in equilibrium.
Unsaturated A solution with less solute than saturation.
Supersaturated
A solution with more solute than
saturation. (Will undergo crystallization
if a crystal seed is present.)
Miscible
Two liquids that dissolve in any proportion.
Henrys Law
S P (S: solubility)
Colligative Properties
Activation Energy
Physical properties of a solution that depends on the concentration of solutes. More solutes will lead to:
Collision model
Reaction Rate
The reaction rate r = d[X]/dt can be determined from the
reaction by the rate law
r = k[A]a [B]b ...
Where a, b, etc. are reaction orders for the reactants. Reaction orders can only be determined experimentally, because reactions will in theory go through several steps, the
slowest of which is the rate-determining step. Reaction order is determined by the number of atoms participating in
the rate-determining step. The sum of these orders is the
overall order.
Concentration function [X] can be determined as
[X]t =
rd + [X]0
0
Reaction Half-time
The half-time of a reaction is the amount of time needed
to consume half of the reactants. It is denoted t1/2 .
For first order reactions, t1/2 0.693/k. For second order
reactions, t1/2 = 1/(k[X]0 ).
Concentration
Definition
(Moles solute)/(Liters solution)
(Moles solute)/(Kilogram solvent)
(Moles solute)/(Moles solution)
(Mass of solute)/(Mass of solution)
(Volume of solute)/(Volume of solution)
Caution: It is an extremely common mistake to confuse
molarity with molality. Check your Rs and Ls!
Spectrophotometry of Concentration
An equilibrium reaction will spontaneously balance an outside eect added to it. For example,
Change in amount of reactants or products: The
reaction will consume more of the substance in excess to
balance the change;
Change in volume or pressure: The reaction will form
more gas if volume increases or if pressure decreases, and
will form less gas if volume decreases or if pressure increases;
Change in temperature: Endothermic reactions will
shift left for lower temperatures and shift right for higher
temperatures. Exothermic reactions will shift right for
lower temperatures and shift left for higher temperatures.
Gas Laws
STP
273 K; 1 atm
Boyles Law
P 1/V
Charless Law
P T
Avogadros Law
P n
Ideal Gas Equation
P V = nRT
Law of Partial Pressure
Pn = Xn Pt
Eusion Rate
u=
(3RT )/M
Grahams Law
u1 /u2 = M2 /M1
Density Formula
d = (P M)/(RT )
Deviation from Ideal Behavior
(P V )/(RT )
Van der Waals Equation
Equilibrium Formulas
Ion-product constant of water
Kw = [H+ ][OH ] = 1.0 1014 (278 K)
Henderson-Hasselbalch equation
pH = pKa + log([base]/[acid])
Van t Ho equation
d(ln K)/dT = (H )/(RT 2 )
ln K = H /(RT ) + S /R
Notation
Molarity (M)
Molality (m)
Mole fraction (X)
Mass percentage
Volume percentage
Le Ch
ateliers Principle
Equilibrium Constant
For reactions in a solution, the equilibrium constant of a
reaction
sS + tT
aA + bB
Is defined as
Kc =
[S]s [T ]t
[A]a [B]b
Stereoisomerism (cont.)
Color change
0.01.6
3.04.6
Large pH
Violet
Blue
3.14.4
4.4-6.2
5.08.0
6.07.6
Yellow
Yellow
Yellow
Blue
8.310.0
Pink
Reduction
Gains electrons
Oxidation num. decreases
Occurs at cathode
Electrochemical Formulas
E = (G)/(nF )
E = E (RT /nF ) ln Q
E = E (0.0592/n) log Q
Nuclear Chemistry
Alpha particles ()
Helium nuclei (42 He)
Beta particles ( )
Electrons (01 e)
Positrons ( + )
Antielectrons (01 e)
Gamma radiation ()
High energy radiation (00 )
Units of radioactivity
SI: Becquerel (Bq): 1 nucleus/s
(Disintegration per second) Curie (Ci): 3.7 1010 nuclei/s
Units of absorbed radiation
SI: Gray (Gy): 1 J/kg
(Energy per kilogram tissue)
Rad: 0.01 Gy
Metallurgy
Metallurgy is the extraction of minerals from ores.
Pyrometallurgy: The use of heat to convert ores to metals. (Example: Production of iron)
Hydrometallurgy: The use of chemical processes in a solution to separate a metal from its ore. (Example: Bayer
process for producing aluminum)
Electrometallurgy: The use of electrochemical processes
to separate a metal. (Example: Hall process for producing
aluminum)
Hydrocarbons
Name
Common Formula Hybridization
Alkane
Cn H2n+2
sp3
Cycloalkane
Cn H2n
sp3
Alkene
Cn H2n
sp2
Alkyne
Cn H2n2
sp
Aromatic
Cn H2n6
sp2
In a hydrocarbon with n carbons, the number of hydrogens
is 2n + 2, minus 2 for each bond or carbon ring.
Stereoisomerism
Stereoisomerism occurs at bonds such as C=C, where both
ends have two dierent substituents, because the rotation
of these substituents are restricted.
Cis-trans isomerism: If both ends have a hydrogen
atom substituent, then the compound exhibits cis-trans
isomerism. The cis-isomer has both hydrogen atoms on the
same side, and the trans-isomer has the hydrogen atoms
on dierent sides.
Cahn-Ingold-Prelog Rules
The CIP Rules are used to compare two substituent groups
in the E/Z and R/S groups of naming isomers.
1. Direct comparison: If the atoms that are directly connected to the stereocenter are dierent,
then the atom with a higher atomic number receives
higher priority.
2. Tiebreaker I: If there is a tie, then a list of atoms
two bonds away from the stereocenter is compiled
for each of the two substituent groups. The atoms
with the greatest atomic number from each list are
then compared. If they tie, then the second greatest
atoms from each list are compared. This process is
repeated until the tie is broken.
3. Tiebreaker II: If there is still a tie after consider
atoms two bonds away from the center, then atoms
three bonds away are considered in the same way in
Tiebreaker I. This process is repeated until the tie is
broken.
4. Isotopes: If two groups dier only in isotopes (and
are otherwise identical), then mass number is used
instead of atomic number in the process.
5. Double and triple bonds: If there is a double bond in the substituent group, then the double bond is treated as a bond with ghost atoms
(e.g. R-A=B-R is treated as R-(A-B)-(B-A)-R).
Triple bonds, similarly, have two ghost atoms for
each atom.
6. Cycles: To handle a molecule containing one or
more cycles, one must first expand it into a tree
(called a hierarchical digraph by the authors) by
traversing bonds in all possible paths starting at
the stereocenter. When the traversal encounters an
atom through which the current path has already
passed, a ghost atom is generated in order to keep
the tree finite.
Criteria of Aromaticity
1. Is cyclic, i.e. possesses a carbon ring;
2. Is planar, i.e. all carbons on the ring are on the same
plane;
3. Has an uninterrupted cloud of electrons;
4. The number of pairs of electrons in the cloud is
an odd number, i.e. the number of electrons in the
cloud is 4n + 2;
then the hydrocarbon is aromatic. Aromatic compounds
are highly stable (cannot undergo addition reactions), but
can undergo substitution reactions.
Functional Groups
Functional Group
R-OH (hydroxyl)
R-O-R (ether)
R-X (halo)
R-NH2 (amino)
R-COH (aldehyde)
R-COX (haloformyl)
R-CO-R (carbonyl)
R-COOH (carboxyl)
R-COO( carboxylate)
R-COO-R (ester)
R-CONH2 (amide)
R-CNH-R (ketimine)
R-CHNH (aldimine)
R-CONCO-R
(imide)
R-N3 (azide)
R-N2 -R (azo)
R-OCN (cyanate)
R-NCO (isocyanate)
R-CN (nitrile)
R-NC (isonitrile)
R-NO (nitroso)
R-NO2 (nitro)
R-ONO (nitrosooxy)
R-ONO2 (nitrate)
R-SH (sulfhydryl)
R-SCN (thiocyanate)
R-NCS
(isothiocyanate)
R-CSH (carbonothioyl)
R-PH3 (phosphino)
R-C6 H5 (phenyl, Ph)
Name
alcohol
ether
haloalkane
amine
aldehyde
acyl halide
ketone
carboxylic acid
carboxylate
ester
amide
ketimine
aldimine
imide
Sux/Prefix
-ol
ether
halo-amine
-al
-oyl halide
-one
-oic acid
-oate
-oate
-amide
iminoiminoimido-
azide
azo
cyanate
isocyanate
nitrile
isonitrile
nitroso
nitro
nitrite
nitrate
thiol
thiocyanate
isothiocyanate
azidoazocyanatoisocyanatocyanoisocyanonitrosonitronitrosooxynitroxy-thiol
thiocyanatoisothiocyanato-
thial
phosphine
benzene der.
Enantiomerism
If a hydrocarbon
Functional Group
Name
Sux/Prefix
R-CH2 C6 H5 (benzyl,
toluene der.
benzylBn)
R-C5 H4 N (pyridyl)
pyridine der.
pyridin-x-yl
Note: In actual compounds, change all instances of halo
above to halogen names (fluoro, chloro, bromo, iodo).
Amino Acids
Hydrophobic amino acids:
Name
Code Name
Alanine
Ala Valine
Phenylalanine
Phe Methionine
Leucine
Leu Proline
Isoleucine
Ile Tryptophane
Code
Val
Met
Pro
Trp
Code
Thr
Cys
Asn
Arg
His
Glu
Protein Structure
Proteins are large biochemical complexes that contain several polypeptide compounds (amino acid chains). They
are organized into four levels of structure:
Primary structure: The chain of amino acids that make
up the protein; this chain directly controls the other levels
of protein structure.
Secondary structure: The patterns formed by segments
of the polypeptide chain; can be either -helices or pleated sheets.
Tertiary structure: The folding of the polypeptide to
produce a certain shape.
Quarternary structure: The geometrical bonding of
several polypeptides to form the protein.
Chirality
c
20092011
Zee Zuo. Licensed under CC-BY-SA 3.0, United States.
System Name
R/S
(+)/()
Based On
Structure
Direction of rotation of polarized
light
D/L
Enantiomer of glyceraldehyde the
molecule is derived from
R/S notation: Orient the enantiomer so that the smallest (by CIP Rules) substituent points backward (away from
the viewer) and the largest substituent points upward. If
the larger substituent of the other two points toward the
right, then the enantiomer is an R-enantiomer. If the larger
substituent points toward the left, then the enantiomer is
an L-enantiomer.
(+)/() notation: An enantiomer that rotates the plane
of polarization clockwise is dextrorotary (+). An enantiomer that rotates the plane of polarization counterclockwise is levorotary ().
D/L notation: An enantiomer that is derived from (+)glyceraldehyde is the D-enantiomer. An enantiomer that
is derived from ()-glyceraldehyde is the L-enantiomer.
Note that nomenclature in a system cannot be determined
by that in another system.
Caution: The (+)/() system is sometimes written as
(d)/(l), which is easily confused with the D, L system. As
these two systems sometimes conflict (a D-enantiomer can
be an (l)-enantiomer), the (+)/() notations are strongly
preferred.
Significant Figures
Significant figures (sig figs) is the number of digits that
carry precision in a number.
Non-measured Numbers: Non-measured numbers,
such as , integer counts, definition of units, etc. always
have infinite sig figs. Other constants, such as NA , have
limited sig figs.
Non-zero Digits: Nonzero digits are always significant,
unless one or more of the other rules are violated.
Zeros: Leading zeros are never significant; trailing zeros,
however, are significant only if they are part of the measurement. Zeros between non-zero digits are always significant.
Reporting Numbers: Reported numbers are only significant to the precision of the equipments with which they
are measured.
Addition/Subtraction: When adding or subtracting
two numbers, the result should have as many decimal
places as the number with the smallest sig figs.
Multiplication/Division: When multiplying or dividing, the result should have as many sig figs as the number
with the smallest sig figs.
Revision 3