Organic Chemistry Chapter 8 Reactions (Alkenes)

When studying this set:

- Focus less on knowing the names of the reactions and more on the reagents and what they do

- Shuffle the terms so you aren't just memorizing the order that we learned the reactions

- Practice with term first to think about how the given reagents will react with an alkene

- Practice with the definition first to think about which reagents are necessary to cause the given reaction

I believe in all of you !!!!

Hydrohalogenation (Markovnikov) *

HBr (or HX)

Markovnikov addition of H and X across the alkene

Hydrohalogenation (anti Markovnikov)

HBr, ROOR

anti-Markovnikov addition of H and Br across the alkene

Acid-Catalyzed Hydration *

H3O+

Markovnikov addition of H and OH across the alkene

Oxymercuration-Demercuration

1) Hg(OAc)2, H2O

2) NaBH4

Markovnikov addition of H and OH across the alkene *without rearrangement*

Hydroboration-Oxidation

1) BH3, THF

2) H2O2, NaOH

anti-Markovnikov addition of H and OH across the alkene, exclusively via a syn addition

Hydrogenation

H2, Pt

syn addition of H and H across the alkene

Bromination *

Br2

anti addition of Br and Br across the alkene

Halohydrin Formation

Br2, H2O

anti addition of Br and OH across the alkene, with OH in the more substituted position

Anti Dihydroxylation

1) RCO3H (peroxy acid)

2) H3O+

treatment of an alene with a peroxy acid converts the alkene into an epoxide, which is then treated with an aqueous acid to give a trans-diol

Syn Dihydroxylation

1) OsO4

2) NaHSO3, H2O

or

KMnO4, NaOH, cold

syn addition of OH and OH across the alkene

Ozonolysis

1) O3

2) DMS

causes cleavage of the C=C bond, giving 2 compounds with a C=O bond

Elimination

NaOMe/NaOEt gives Zaitsev product (more substituted)

t-BuOK gives Hofmann product (less substituted)