Reagents for OChem

H2, Pd/CaCO3, Pb(OAc)2 (Lindlar catalyst)

Syn Reduction to from triple bond to double bond

NaNH2/NH3(li)

Rip a Hydrogen off alkyne and make it a highly reactive nucleophile.

TsCl, pyridine

make the alcohol a good O-Ts Leaving group

Hg++ (catalyst), H3O+

Classic Markovnikov but on a triple bond, rearranges to a ketone.

CrO3–pyridine–HCl (PCC

Oxidizes primary alcohols down to ketone but not all the way to carboxylic acid.

CrO3,H2O

Strong oxidant all the way to carboxylic acid.

H5IO6

Split two alcohols breaks the bond

Mg, diethyl ether

Grignard reagent

(1) BH3-THF; (2) H2O2, NaOH

Antimarkovnikov OH

meta-chloroperoxybenzoic acid mCPBA

Add epoxide to double bond

(1) OsO4, TMAO

Double OH addition

KOC(CH3)3, DMSO

Elimination zaitsev.

(1) O3; (2) CH3SCH3

Double bond cleavage reductive workup

(1) O3; (2) H2O2, H2O

Double bond cleavage oxidative workup