chem 1820

pka of 60

alkane

pka of 40

alkene/amine — more acidic

pka of 25

alkyne

pka of 15

alcohol, water

pka of 10

protonated amine

pka of 5

carboxylic acid

pka of 0

protonated amine, protonated oh, cooh

electron withdrawing groups ___ acidicy, edg ___ acidicy

increase, decrease

increasing number of carbons (boiling point, solubility)

increases the boiling point, decreases the solubility

increasing branching (boiling point, solubility)

decreases boiling point, increases the solubility

rank the solubility in water (least to most) —→ alkyl halides, ethers, amines, alcohols and alkanes

alkane<alcohol=ether<amine<alkyl halides

chair flip

everything stays up if up originally but change from equatorial to axial (or vice versa)

cis chair conformation

both up (doesn’t matter if equatorial or axial both or neither or one)

trans chair conformation

one up one down

to see relationship between two molecules (odd # of switches ___, even # ____)

enantiomer, diastereomer (think: if switch one, you get an enantiomer)

electrophile

electron loving (like an acid)

nucleophile

electron donating (like a base)

hydrohalogenation (like alkene with HBr)

markonikov, regioselective, both syn and anti, carbocation is formed

hydrogenation (H2 with pd)

syn addition

acid-catalyzed hydration (H30+)

h30+ or h20/h2so4 markonikov, syn and anti, carbocation is formed

addition of alcohol to alkene

alcohol/h2so4 markonikov, mix of syn and anti, carbocation formed

hydroboration oxidation (for alkenes)

bh3/thf ho-, h202, h20, anti markonikov, syn, no carbocation formed

halogenation (br2, for example) — without competition

br2 with ch2cl2 neither markonikov or anti markonikov bc add to both sides, anti addition, no carbocation formed

halogenation with competition (br2)

br2, h20, oh adds to more substituted, br to less, anti additon, no carbocation formed

epoxidation

RC=OOOH, syn, no carbocation intermediate formed

ozonolysis

O3, -78degrees c/ (ch3)2s, syn, no carbocation intermediate formed

1,2 kinetic or thermodynamic

kinetic always

1,4 kinetic or thermodynamic

thermodynamic sometimes

increase reactivity with EWG in ___ and EDG in ___ (what makes something electron withdrawing, waht about electron donating?)

dienophile, diene (electronegative, positive charge, resonance ouside pi system — ewg, lone pairs, negative charge, resonance towards pi system— edg)

diels alder

syn additon, endo forms faster,

Hbr with ROOR

radical reaction, anti markonikov, both syn and anti, only works on Br, radical shifts

nbs

markonikov, attacks allylic carbon, anti addition, radical shifts

br2 with light and alkane

adds once, markonikov,

addition of halogen to alkyne

br2/ch2cl2, anti addition (not both), no carbocation, PI COMPLEX

h20 to alkyne

h20/h2so4, markonikov, anti-addition, enol to ketone

h2/ lindlars

cis, syn addition

na/nh3

trans, anti

hyroboration oxidation (alkynes)

R2BH/THF HO-,H2O2, H2O, tautemerixation, antimarkonikov, syn, no rearrangement

Sn2 (weak or strong base, how many steps, bulky/not bulky, which more reactive)

one step, no carbocation formed, want strong nucleophile, not bulky, primary is most reactive, (teritary doesn’t react), aprotic

Sn1 (weak or strong base, how many steps, bulky/not bulky, which more reactive, which solvent)

weak base, many steps, not bulky, teritary, protic

E2 (weak or strong base, how many steps, bulky/not bulky, which more reactive, which solvent)

strong, one step, bulky —> zaitsev (but non-bulky —> hoffman) works too), teritary (for boht!!), aprotic

E1 (weak or strong base, how many steps, bulky/not bulky, which more reactive, which solvent)

weak, two steps, bulky —> zaitsev, non-bulky —> hoffman, teritary (for both), protic,

protic

contains O-H or N-H