Reagents

HCl, HBr, HI

markovnikov HX addition

HBr/ROOR, HBr/HOOH

anti markovnikov HX addition

NBS/DMSO, NBS/Heat

allylic bromination, retains double bond

Br2, Cl2

anti addition of X/X

Br2/H20, Cl2/H20

markovnikov anti addition of OH and X

Br2/ROH, Cl2/ROH

markovnikov anti addition of OR and X

Hg(Oac)2H2O/NaBH4

markovnikov addition of OH, no rearrangements

HgSO4, H20/H2SO4

markovnikov addition of OH

1. BH3THF/2.NaOH,H202

anti markovnikov syn addition of OH, +en

1. Sia2BH/ 2. H2O2,OH-

anti markovnikov addition of ketone/aldehyde (double bonded O)

H2/Pd, H2/Pt, H2/Ni

reduces all bonds to single bonds

t-BuO, NaOCH3, NaH (strong, bulky bases)

E2

NaNH2

double elimination or deprotonation

K2Cr2O7/H2SO4, CrO3/H2SO4, H2CrO4

primary alcohols to carboxylic acid

converts secondary alcohols to ketones,

PCC, NaOCl/Tempo, NaOCl/AcOH, DMP

primary alcohols to aldehydes

secondary alcohols to ketones

TsCl/py, SoCl2, SOBr2 (SN2 inversion) , PBr3, PCl2 (both with SN2 inversion)

replaces OH with good leaving group (Br or Cl)

LiAlH4/H30

opens epoxide ring, nucleophile attacks least subbed C, least subbed C gets inversion of configuration

mcpba, MMPP, CH3CO3H

formation of epoxide

H2/lindlar

alkyne to cis alkene

Na/NH3, Li/NH3

alkyne to trans alkene

OsO4/NaHSO4,H20. , KMnO4 (cold)/H20,OH

syn dihydroxylation

O3/CH3SCH3, O3/py, O3/ZnH3O

cleavage of double bonds, adds O

H2SO4/H20

markovnikov addition of OH

H2SO4/heat

removes OH forms alkene