Organic Chemistry Final Transformations

HYAH

1. BH3 (THF)

2. NaOH, H2O2

1. O3

2. (CH3)2S

1. Hg(OAc2)2, H2O

2. NaBH4

HBr

Br2, EtOH

Br2, CH2Cl2

reagents?

H2SO4, MeOH

reagents?

B. HBr, ROOR

C. KotBu (or other bulky base)

1. O3

2. H20

H2SO4, H2O

HgSO4

1. 9-BBN (THF)

2. NaOH, H2O2

excess HBR, ROOR

NaNH3

Lindlar cat, H2

D

1. NaNH2 (xs)

2. H20

E

HBr (xs)

1. NaNH2

2. Br + isopropyl

mCPBA

1. BH3(THF)

2. NaOH, H2O2

HBr, ROOR

HBr

1. Hg(OAc)2, H2O

2. NaBH4

H2SO4, CH3OH

Br, CCl4

Br2, H2O

KMnO4, cold, NaOH

1. O3

2. H2O

H2SO4, H2O

HgSO4

1. 9-BBN

2. NaOH, H2O2