Alkene Wheel

OChem Fall25

10

1) O3

2)DMS

9

1) OsO4

2) NaHSO3, H2O

9

1) KMnO4

2) NaOH cold

8

1)RCO3H

2)H3O+

7

Br2, H2O

6

Br2

5

H2, Pt

4

1) BH3, THF

2) H2O2, NaOH

3

1) Hg(OAc)2, H2O

2) NaBH4

3

H3O+

2

HBr, ROOR

1

HX

9

Syn Dihydroxylation

8

Anti Dihydroxylation

8

Forms epoxide

5

Hydrogenation

6

Halogenation

1

Hydrohalogenation

2

Hydrohalogenation

3

Acid-catalyzed hydration

3

Oxymercuration-demercuration hydration

4

Hydroboration-oxidation hydration

10

Oznolysis

Adding two syn OH

1) OsO4

2) NaHSO3

OR

1) KMnO4, NaOH cold

Adding 2 anti OH

1) RCO3H

2) H3O+

Adding anti Bromines

Br2

Adding syn hydrogens

H2, Pt

Adding syn H and OH

1) BH3, THF

2) H2O2, NaOH

Adding H and OH markov.

1) H3O+

OR

1)Hg(OAc)2, H2O

2) NaBH4

Adding H and Br (anti markov)

HBr, ROOR

Produces a ketone and aldehyde

1)O3 2)DMS

Adding H and Br (markov)

HX

10

oznolysis