Solvents and Substrates

HX

HX

ROOR

H3O+ (H2SO4, H2O)

Hg(OAc)2, H2O

NaBH4

BH3 x THF

NaOH, H2O2

Br2

Br2

H2O

mCPBA

H3O+

OsO4

NMO

O3

DMS

H2

Lindlar's catalyst

H2

Pt

Na

NH3 (l)

Alkyne goes through

HgSO4

H2SO4, H2O

Alkyne goes through

9-BBN

NaOH, H2O2

Alkyne goes through

xs HX

Alkyne goes through

HX

Alkyne goes through

X2

CCl4

Alkyne goes through

xs. X2

CCl4

Alkyne goes through

O3

H2O

Alkyne goes through

NaNH2

RX

Ketone goes through

H2

M Catalyst

(if multiple double bonds, both get taken out, making it worse/ less selective)

Ketone goes through

NaBH4 or LAH

(LAH better because it can do ester)

Ketone goes through

RMgX

Ketone with OH attached goes through

TMSCl, Et3N

Mg

Specefic Carbonyl

H2O

TBAF

Protection, adds specific carbonyl

Alcohol goes through

Na2Cr2O7

H2SO4, H2O

Alcohol goes through

PCC

CHCl2

or

DMSO, (COCl)2

Et3N

or

DMP

CH2Cl3

epoxide ring goes through

strong nucleophile

H20

Anti addition of OH/Nu, nuc attacks less substituted and O goes to more substituted

Epoxide Ring goes through

weak nucleophile (H2SO4/MeOH,HBr)

anti addition of OH/nuc, nuc attacks more substituted side and O goes to less substituted

Double bond goes through

mCPBA

Alcohol goes through

HX

Alcohol goes through

HCl

ZnCl2

Alcohol goes through

SOCl2

Py

Alcohol goes through

PBr3