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VSEPR Theory: domains of electrons around a central atom will orient themselves to minimize the electron- electron repulsion
between the domains
Bond Angles
# of Domains 2 180 BeH2, O2N+, CO2
3 120 BH3, H3C+, CH2
4 109.5 Ch4, NH3, H2O
5 Molecular Shapes
Name AXmEn Notation Geometry Idealized Bond Angles
Linear AX2 180
R, Y, Z placeholders
1. R H or Alkyl Group (CnHm)
2. X F, Cl, Br, or I (halogens)
3. Z any group/ group of atoms
Types of Orbitals
1. Head to head overlaps sigma () bonds
2. Side to side overlaps- pi () bonds
Hybridization; combining s and p orbitals to form an equal number of new orbitals that are averages of the originals
Single bonds can rotate freely but double bonds cannot because the portion of a double bond prevents the bond axis from rotating
sp2 3 120
sp 2 180
2. Hydrobromic acid
3. Hydrochloric acid
5. Nitric Acid
Strong Bases- Accepts an H+, an ion with lone pair and -1 formal charge localized on an H, C, N, or O atom
1. Hydride Ion
2. Hydroxide
3. Methoxide
4. Ethoxide
5. Tert-butoxide
Any molecule containing an H can serve as an acid, and any molecule with a lone pair (or a bond) can be a base
Arrow Rules
1. Arrow must come from either a lone pair or a bond
2. Arrows point to atoms that either get a new lone pair or make a new bond
pKa: measure of the energy difference between the conjugate acid (H-Z) and the conjugate base (Z-) in the solvent, water
Positive pKa breaking bond (+/uphill);
Negative pKa making bond (-/downhill)
High pKa = weak acid; Low pKa = strong acid assume all six strong acids are pKa = 0
Strong base= molecule with lone pair and -1 charge on H, C, N, O assume that strong bases have a pKa > 14
For a given base, the higher the pKa of its conjugate acid, the stronger the base
For a given base, the lower the pKa of its conjugate acid, the weaker the base
Most acidic H requires the least amount of energy to remove and tied to the strongest acid molecule
Inductive Effect: polarization caused by an electronegative atom (ex: F) can induce minor polarization in neighboring bonds (localized
effect); weak so it cannot change that an H on a positively charged atom is more acidic than an H on a neutral atom, or that an H on N
or O is more acidic than an H on C
Nomenclature Workshop
Alkane= molecule consisting entirely of carbon and hydrogen atoms connected by single bonds
Parent chain= longest continuous chain of carbon atoms found in branched molecule
Molecule can have more than one parent chain of equal length
4 sec-butyl
4 tert-butyl or t-butyl
5 -CH2CH2CH2CH2CH3 pentyl
Resonance: demonstrates charges that are delocalized (shared) among multiple atoms
Arrow Rules
1. Type 1: A lone pair of electrons becomes a bond to an adjacent (next- door) atom
2. Type 2: A pair of electrons in a bond slides down to become a lone pair on one atom in that bond
3. Type 3: A pair of electrons in a bond to an adjacent (next-door) atom
4. For most Anions: Use one Type 1 and one Type 2 in tandem to move a (-) charge
5. For most Cations: Use on Type 3 to move a (+) charge
6. Arrows are only used to move electrons to an adjacent (next-door) atom or bond
7. You may not move electrons in a sigma bond, move any atoms, change the total number of electrons, or change the number
of formal charges
8. Each C, N, O, X atom must have an octet (carbocation [R3C+] are acceptable)
Important or first order resonance structures defined as those with the minimum number of +1 and -1 formal charges (and no
formal chargers larger than +/- 1)
Electron in a Box analogy: for two similar molecules, the one with more resonance structures will be lower in potential energy
because they are resonance stabilized
Resonance Effect
1. Delocalized electrons have a greater wavelength because they spread out electrons (decrease in reactivity)
2. Resonance structures increase wavelength (low P.E. more stable)
3. Electrons can behave like waves
4. (-) Charge stuck on more electronegative atom for stabilization
Carboxylic acids [RCOOH] are acidic (pKa=5, ex: Acetic Acid)
Types of Conformations
Staggered (180): bonds on one carbon bisect the bond angle on the adjacent carbon when viewed looking down the C-C
bond, H is staggered; favorable (downhill)
Staggered Anti (180): two largest groups are on opposite sides of the structure/diagram
Eclipsed (120): bonds on adjacent carbons are aligned as viewed looking down the C-C bond; H is lined up eclipsing one
another; most unfavorable (uphill)
Staggered Gauche (60): methyl groups are staggered but next to each other
Fully eclipsed (0): when the methyl groups eclipse each other
Most favorable conformation is the relative position in space that H is occupying Steric
1. Steric hindrance- positioning of atoms forces them closer together, increasing the amount of steric strain in the molecule
2. Stabilization of the staggered conformation by hyperconjugation
3. Repulsion between bonding pairs (electrons in C-H bonds)
In general, high potential energy systems are unstable and likely to change if they have a way to change
Ethane spends the most time in the lowest PE position (staggered) so you would be most likely to catch ethane in that position
Potential energy wells of the staggered conformations
Isomers: compounds with the same molecular formula but have different structures
*Two molecules are the same if they can be interconverted without breaking any bonds
Alkenes: compounds containing only C and H with a C=C bond are known
Determining cis/trans for rings that lie in the plane of the paper (wedge vs. dash)
If both groups are attached to the same carbon groups are neither cis or trans to one another
If both groups lie on the same side of the plane of the paper groups are cis to one another (both wedge)
If the groups lie on opposite sides of the paper groups are trans to one another (one wedge, one dash)
*You cannot buy a bottle of anti butane because in any sample of butane at normal temperatures the molecules are rapidly
interconverting among al possible conformations. You can buy a bottle of cis-1, 3-dimethylcyclohexane
Ring strain: type of instability that exists when bonds in a molecule form angles (>109.5) that are abnormal (ex: cyclopropane)
Chair conformation: cyclohexane is the only size of ring that adopts this conformation lowest potential energy of cyclohexane and
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