organic chem to remember

primary alc + HX

sn2

tertiary alc + HX

sn1

primary/secondary alc + PBr3

sn2, stereochem flip

primary/secondary alc + SOCl2

sn2, stereochem flip

secondary alc + HX

sn1, racemic mixture

alkene + HBr

mark, no stereochem

alkene + HBr + ROOR

anti, racemic mixture

alkene + mCPBA

syn addition of an epoxide

alkene + Br2

anti

alkene + Br2 + H2O

anti, OH mark

alkene + H2O + acid (H+, H2SO4)

OH addition, mark, rearrangements

alkene + Hg(OAc)2 H2O, NaBH4

OH addition, mark, NO rearrangements

alkene + BH3 THF H2O2 OH

H mark, OH on other side, anti, +en

secondary alkyl halide + KOH, heat

alkene, E2

secondary alkyl halide + NaCN

replace halide with CN, Sn2

secondary alkyl halide + EtOH

OEt, Sn1

tertiary alkyl halide + H2O

OH, Sn1

tertiary alkyl halide + H2O, heat

OH, E1

tertiary alkyl halide + KOH, heat

ALKENE, E2

acid or base: NaNH2

base

acid or base: NaOH

base

acid or base: NH3

acid 35

acid or base: H2O

acid 16

acid or base: ROH

acid 16

acid or base: NaH

base

acetylide addition

alkyne + NaNH2/NaH !NO NaOH!

grinard reactant

R-Mg-X

grinard RULES

cannot contain, OH, triple bond, NH2, Sh

ALC IS NOT A MOTHAFUCKIN

leaving group.

secondary alc + HX

DNE DIH

acid catalysed dehydration

ROH + acid + heat = alkene

alkyl halide + terbutoxide

alkene!

pinacol rearrangment turns a ___ into a ___

alc into a ketone

if you increase carbon and oxygen bonds?

oxidation

increase carbon and hydrogen bonds?

reduction :(

alkene + H2 + Pd/C

alkane

primary alc + jones

carboxylic acid

secondary alc + jones

ketone

primary alc + pcc

aldehyde

secondary alc + pcc

ketone

what does a breathalyzer do?

oxidize ethanol!

ROH + SOCl2 = inversion of stereochem…. add NaBr and acetone

inverts again

ROH + TsCl = no inversion… add NaBr and acetone

inverts!

alc protecting groups

TMS-Cl and TiPs-Cl with TBAF

what are we doing in a protecky?

making a aldehyde an OH and whatever we want to add

williamston either synthesis

Sn2, make an ether from an alc using NaH, NaNH2, or Na then an alkyl halide of whatever you want to add

primary acid catalysed cleavage

Sn2

tertiary acid catalyzed cleavage

Sn1

how do you open an epoxide ring? BASIC

Sn2 with (EtO^- and H3O⁺) or (NaOH and H2O) or (grinard + acid) or (LiAlH4) or (XS NH3)

how do you open an epoxide ring? ACIDIC

Sn2, (acid + H2O) or (HX)

epoxide openings acidic

nuc attacks tertiary side first, if not attack least hindered

number of p orbitals =

number of MO’s

conjugated alkene + HX -78C

1,2 kinetic product 80%

conjugated alkene + HX 40C

1,4 thermodynamic product 85%