Organic Chemistry (Ch. 8 and 9) Reactions

1)O3 2) DMS

Ozonolysis of an alkene

HX

Hydrohalogenation (Markovnikov)

HBr, ROOR

Hydrohalogenation (Antimarkovnikov) - only with bromine

H3O+ OR H+, H2O

Acid catalyzed hydration of an alkene (Markovnikov)

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

Oxymercuration Demercuration (Markovnikov)

1) BH3-THF 2) H2O2, NaOH

Hydroboration Oxidation (Anti-markovnikov) +en

H2, Pt (Alkene)

Hydrogenation (Alkene → alkane)

Br2

Bromination (Br to both positions) +en (anti addition)

Br2, H2O

Halohydrin Formation (OH → more sub. Br → less sub.) +en (anti addition)

1)RCO3H 2)H3O+

Anti-dihydroxylation (OH to both positions) +en (anti addition)

1)OsO4 2)NaHSO3, H2O

Syn-dihydroxylation (OH to both positions) +en (syn addition)

1)xs NaNH2 2)H2O

Elimination (Alkane → alkyne)

HgSO4, H2SO4, H2O

Acid catalyzed hydration of an alkyne (Forms Keytone = Markovnikov)

1)R2BH (9BBN) 2)H2O2, NaOH

Hydroboration Oxidation (Forms Aldehyde = anti-markovnikov)

1)O3 2)H2O

Ozonolysis of an alkyne (fully oxidized = internal alkyne → 2 carboxylic acids, external alkyne → 1 carboxylic acid, 1 C double bonded to two Os)

1)NaNH2 2)RX

Alkylation (Only way to add carbons) (Must have a LG on the group being added)

Na, NH3 (l)

Dissolving metal reduction (alkyne → trans alkene)

H2, Lindlar’s Catalyst

Hydrogenation with a poisoned catalyst (alkyne → cis alkene)

H2, Pt (Alkyne)

Hydrogenation (Alkyne → alkane)