Quicksheets OChem Flashcards
SN1 How many steps When is it favored Calculation of Rate ranking product type strong nucleophile?
SN1 2 steps favored in polar protic solvents 3 > 2 > 1 > methyl rate = k[RL] Racemic products strong nucleophile not required
SN2 How many steps When is it favored Calculation of Rate ranking product type strong nucleophile?
SN2 1 step concerted favored in polar aprotic solvents methyl > 1 > 2 > 3 rate = k[Nu][RL] Optically active and inverted products Favored w/ strong nu
nucleophilicity trends: charge electronegativity steric hindrance solvent
Nucleophilicity increases with increasing electron density (more negative charge)
It decreases as electronegativity increases
bulkier molecules = less nucleophilic
protic solvents can inhibit nucleophillicity by protonating the nu or through H bonding
Aprotic solvents trend for nucleophilicity in terms of halogens
F- > Cl- > Br- > I-
Protic solvents trend for nucleophilicity
in protic solvents, good bases pick up protons and are wors enucleophilies
I- > Br - > Cl- > F-
main thing to increase nucleophilicity
nucleophilicity is increased by increasing electron density
main thing to increase electrophilicity
electrophilicity is increased by increasing positive charge
most common leaving groups
- weak bases
- Large groups w/ resonance
- Large groups w/ electron-withdrawing atoms
which types of configuration have opposite stereochemistry at every chiral carbon but, for the most part, the same chemical and physical properties
enantiomers
which types of configuration differ at some but not all chiral centers and have different chemical and physical properties
diastereomers
single bond:
Bond type =
hybridization =
angles =
single bond:
Bond type = sigma
hybridization = sp3
angles = 109.5
PCC
primary alcohol to aldehyde
Jones reagent
Jones’s reagent = KMnO4 =
secondary alcohol -> ketone
primary alcohol -> COOH
treatments of phenols with oxidizing agents produces
quinones
synthesis of aldehydes (2)
oxidation of primary alcohols
ozonolysis of alkenes
