O Chem 1

dissociates to give H+

donates H+/proton

e- acceptor

dissociates to give OH-

accepts H+/proton

e- donor

• unshared e- pair/ π bond
• - /neg charge
• "nucleus-loving"
• lewis charge

• stronger -/neg charge, higher nucleophilicity;
• basicity incr so does nucleophicity;
• ↑basicity = ↑nucleophilicity

• +/pos charge
• "electron loving"
• lewis acid
• incomplete octet

• sharing e- through covalent b.
• electronegative = electron withdrawing
• not electronegative = electron donating
• * alkyl gr --> electron donating
• (alkyl -- alkane missing one H ; smallest methyl CH₃-)

• give e- density to bond
• = more basic = less acidic

• take away e- density from bond
• = less basic = more acidic

- more stable by spreading charge

*delocalization: moving electrons b/w p-orbitals incr stability

• 1. can only go through p orbitals
• 2. can only move through lone pairs or π bonds
• 3. + charges end up on the non-electroneg atoms
• 4. - charges end up on electroneg atoms

- the more stable intermed, easier for rxn to occur

- stabilize through induction

- degree of substitution refers to the # of substituents on an atom

• electron poor: carbocations - cabonium
• radicals

electron rich: carboanions

move H- : to form more stable (more stable 2^o subst --> 3^o subst)

• ONLY CARBOCATIONS
• 

• (ONLY WKS W/ CARBOCATIONS)
• 

• 1. Assign priority based on atomic #
• - heavier isotope 1st
• - same atom, move one out
• - break apart multiple bonds

2. Move the 4th group into back

• 3. Go 1 → 2 → 3
• CLOCKWISE R
• COUNTER S

4. If you had to do step 2, switch R → S or S → R

• - all chiral centers are opposites
• - come in pairs
• - > 1 chiral centers
• - optical activity, same magnitude
• opposite sign
• - all other properties the same
• - resolution way to separate them
• - 50/50 mixture = RACEMIC MIXTURE

• - 1 line of symmetry & EVEN # OF CHIRAL
• - no optical rotation

• - some but not all chiral centers are opposite
• - 2 or more molecules
• - separate via fractional distillation

substitution nucleophilic 2 bimolecular (2nd order)

• [SN --> happens all at once]
• SN2 --> chick (base) wants guy, girl sneaks in & kicks out other
• 

• 1. reactivity based on steric hindrance
• methyl > 1^o > 2^o > 3^o

2. solvent -- aportic (have Nu ^- want to remain unstable)

• 3. Inversion of stereochemistry
• R → S
• S → R

unimolar (1st order)

• [SN --> happens all @ once]
• SN₁ guy is (base) waits for guy to leave & go in
• 

• 1. Based on stability of carbocation
• 3^o > 2^o > 1^o > methyl

2. Solvent: protic

3. Get RACEMIC mixture

4. Shifts can occur

- incr bond order

• E1--> waits to come off
• 

• 1. Reactivity based on carbocation stability
• 3^o > 2^o > 1^o > methyl

2. Polar protic (stabilize hylide/ leaving gr from attacking again)

3. TRANS is more stable

4. Shifts can occur

5. Need β-hydrogen

occurs w/ alkyl halide ONLY

• E2 --> all @ one time
• 

1. Reactivity based on sterics of base (more constituents is better, not always)

• 2. Large base → least substituted
• Small base → more substituted

3. No shifts

4. *Must be anti to the leaving gr

1. HEAT: ↑ heat gives reactants enough energy to overcome the increased Ea

2. STRONG BASE: eliminations rxn use bases, not nucleophiles

3. 3^o OR 2^o: Both E rxn prefer 3^o substitution & are minimally affected by sterics