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45 Cards in this Set

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Carbon prevalence
Makes up less than 1% of earth's crust, what is most prevalent?
Si, Al, and O2
Are all compounds containing carbon considered organic?
No, what doesn't get included?
pure carbon compounds (such as graphite, diamond, Bucky Balls, nanotubes), CO2, calcium carbonate, etc.
Why is carbon so special?
Can form strong single bonds with itself.
What are isotopes, ions, and elements?
differing number of neutrons are isotopes
differing number of electrons are ions
elements differ by number of protons
How do you calculate formal charge?
(Valence) - (# of bonds) - (# non-bonded electrons)
# of bonds & lone pairs?
Boron
Carbon
Nitrogen
Oxygen
Fluorine
3, 0
4, 0
3, 1
2, 2
1, 3
Draw out memorized set of periodic table
H——————————————He
Li—Be———B—C—N—O—F—Ne
Na————————P—S—Cl—Ar
K————————————Br—Kr
What 2 factors contribute to a bond dipole?
Differences in electronegativity
Bond length
When you see Na-sth or K-sth...
Cross out spectator ion from group 1 and write in charge on anion
What moves in resonance?
electrons (NEVER move the charge)
Which ones?
lone pairs & pi bonds
To start on resonance problems...
move electrons towards positive charge
Why?
Because positive and negative attract.
What are road blocks in resonance structures?
sp3 hybridized atoms
How do I choose the major resonance contributor?
#1: Octet Rule
If octet rule is fulfilled for multiple structures, where should the negative charge be?
On the most electronegative atom.
Also, minimize separation of charge.
What is an empirical formula?
simplest, whole-number ratio of elements in a compound

With what else could you determine molecular formula? How?
molar mass

Divide molar mass by empirical mass to get factor by which to multiply empirical numbers.
Molar Mass of
Hydrogen?
Carbon?
Nitrogen?
Oxygen?
1 g/mol
12 g/mol
14 g/mol
16 g/mol
What is a molecular formula?
The total number of each element in a molecule of a compound.
What is a structural formula?
Elucidates the Lewis structure of the molecule.
Rules for writing condensed structural formula?
CH2's in a row counted and written as (CH2)n
CH3's connected to same carbon written as (CH3)n

What is deuterium and its symbol?
Heavy hydrogen (1 neutron), D (must still be drawn in on line-angles)
Arrhenius acids and bases
Acids dissociate in H2O to give H3O+
Bases dissociate in H2O to give OH-
Lewis acids and bases
Acids accept electrons (electrophiles)
Bases donate electrons (nucleophiles)
Bronsted-Lowry acids and bases
Acids donate protons
Bases accept protons
What is the difference between 2 conjugates (acid/base)?
1 proton
What is the periodic trend for acid strength?
When the proton of interest is bonded to different elements, acidity increases left to right, top to bottom
What other factors increase acidity of a molecule?
Electron-withdrawing groups (halogens, NO2, C=O) near acidic proton. More electronegative = stronger effect.
How?
They help stabilize the conjugate base.
During acid comparisons...
check to see if molecule may be a carboxylic acid (acidic) or an alcohol (NOT acidic).
What are the strong acids?
HCl
HBr
HI
H2SO4
HNO3
HClO4
Strong acid creates..
Weak conjugate base
Strong base creates...
strong OR weak conjugate acid
Weak acid or base creates..
Weak OR strong conjugate
What strong bases have we seen up until now?
hydroxide and alkoxides are the weakest of the strong bases (anything above that on the table will be strong)
pKa
refers to acid strength
< 0 - very strong
0-5 moderately strong
5-15 moderately weak
15+ weak
(higher Ka = lower pKa = stronger acid)
pKa of CH4
45-50
pKa of NH3
about 35
pKa of terminal alkyne
about 25
pKa of alcohol
15-18
pKa of water
15.7
pKa of phenol
10
pKa of carboxylic acid
4-5
How do I rank a series of bases in order of increasing/decreasing basicity?
1. Convert to acids
2. Determine approx. pKa
3. W/in category, rank on electron-withdrawing groups
4. Reverse acid strength order
How do I determine if a base is strong enough to quantitatively deprotonate an acid?
If you start from the acid in question, go across to its conjugate. Conj. will not be strong enough, and you will have equilibrium.

Any base that is stronger than the conjugate (higher on the list that orders acids and bases), will be able to completely deprotonate the acid.
degenerate orbitals
orbitals with identical energies (p. 4)
covalent bonding
ionic bonding
occurs through sharing of electrons
attraction of oppositely charged ions (usually forms 3D lattice structure)
polar covalent bond
electrons shared unevenly
What makes a molecule stable?
Dispersion of charge therefore...
having resonance structures makes a molecule incredibly stable