addition to alkenes

hydrohalogenation (HX - HBr, HCl, HI)

X on more substituted, H on less substituted, syn and anti addition, transition state = carbocation on more substituted carbon

radical HBr addition (HBr, ROOR/light)

Br on less substituted, H on more substituted, syn and anti addition, transition state = radical on more substituted carbon

acid catalyzed hydration (H2O cat H2SO4)

OH on more substituted, H on less substituted, syn and anti addition, transition state = carbocation on more substituted carbon

mercuric acetate reduction (1. Hg(OAc)2 2. NaBH4)

OH on more substituted, H on less substituted, syn and anti addition, transition state = 3 membered ring containing HgOAc+

halohydration (X2 and H2O)

OH on more substituted, X on less substituted, anti addition, transition state = 3 membered ring containing X+

hydroboration (1. BH3 2. NaOH, H2O2)

OH on less substituted, H on more substituted, syn addition, transition state = H and B add at same time to same face of alkene 

X2 addition (X2 - B2, Cl2, I2)

X on more substituted, X on less substituted, anti addition, transition state = 3 membered ring containing X+

dihydroxylation (1. OsO4 2. NaHSO3)

OH on more substituted, OH on less substituted, syn addition, transition state = two oxygens of OsO4 add at same time to same face of alkene

metal catalytic hydrogenation (H2, Pt or Pd or Ni)

H on more substituted, H on less substituted, syn addition, transition state = H2 and alkene form bonds to metal surface

cyclopropanation (CHCl3, KOt-Bu)

two bonds attached to CCl2, syn addition, transition state = carbene intermediate 

ozonolysis (1. O3 2. Me2S)

two carbonyl products

RX addition to alcohol leaving group

2 or 3, SN1

H3PO4 addition to alcohol leaving group

2 or 3, E1

PBr3 addition to OH leaving group

1 or 2, SN2

TsCl addition to OH leaving group

1, 2, or 3

Williamson Ether synthesis

RO- Na+ —> Br —> ROR (ether)

this is just an SN2 reaction

two alcohols acid catalyst ether formation 

2x ROH —> cat. H2SO4 —> ROR

this is an SN1 reaction with two alcohols

to make alkyne from alkene

Na+NH2-