OCHEM REACTANTS AND PRODUCZTS

Hydrohalogenation

Halogen is added to the more substituted carbon unless ROOR is present

Hydrohalogenation reagents

HBr, HCl

Acid-Catalyzed Hydration

Adds an OH group to more substituted carbon

Acid Catalyzed reagants

H3O/H2SO4

Oxymeric Demercuration

Reaction where OH group is added to more substituted carbon

Reagents for Oxymericdemurcuration

1) Hg(OAc)2, H2O 2) NaBH4

Hydroboration-Oxidation

OH group is added on to less substituted carbon, and H is added to more substituted carbon with trans stereospecifity

Reagent used for hydroboration-oxidation

1) BH2 x THF 2) H2O2, NaOH

Catalytic Hydrogenation

Results in syn addition of hydrogen atoms on both sides of double bond

Halogenation

Br is added trans on each side of double bond

halohydrin Formation

OH attacks more substituted side and is added trans to BR

Reagents that produce halohydrin formation

Br2, H2O

Anti Dihydroxylation reagents

MCPBA,1)RCO3H 2) H3O, 2) [H2SO4]

Syn Dihydroxylation

OsO4, NMO,/ OSO4 NaHSO3/ H2O

Primary mechanism with strong base Strong nucleophile with primary carbocation

SN2

Primary mechanism with strong base strong nucleophile and secondary carbocation?

E2

Primary mechanism with strong base strong nucleophile and tertiary carbocation?

E2

Primary mechanism with any carbon and strong base weak mechanism

E2

Primary Mechanism for Strong nucleophile weak base and Primary or secondary carbocation

Sn2

Primary mechanism for weak base strong nucleophile and tertiary carbocation

Sn1

Primary mechanism for weak base weak nucleophile and tertiary carbocation

Sn1/E2 (Depends on reagent)

Weak base Strong nucleophile reagents

RS-, I- NC-

Strong base Strong nucleophile

RO-, RNH-

Strong base weak nucleophile

NaH, DBU, DBN, TBuOK

Weak Base Weak nucleophile

ROH, H2O