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x2

x2 / H2o

1. hg(oac)2, H2O 2. NaBH3

1. BH3, THf 2. H2O2, OH-

mCPBA, ch2cl2

1.mCPBA,ch2cl2 2. H3O+

1. O3 2. Zn, CH3OOH/CH3CH2OH

KMNO4, H3O+

1. OsO4, pyridine 2. HIO4
1. epoxidation then splitting into two ( makes aldehydes)
CH2I2, Zn(Cu), ether

ChCl3 / KOH

KOH / CH3CH2OH

H2SO4, H2O / THF, heat

H2, Pt

H2O, H3PO4, cat + heat

1. OsO4, pyridine 2. NaHSO3, H2O

1. NaNH2 2. H3O+

koh / ethanol

hbr(1eq)/ch3co2h

br2(1eq)/ch3co2h

cl2(2eq)/ch3co2h

h2o , h2so4/ hgso4

H3o+ / hgso4

Bh3, thf / 2. H2o2, naoh

h2/ pd/c

h2/ lindlars catalyst

li/ nh3

Kmno4 OR o3

1.br2 2. Nanh2

1. Nanh2 / 2. rx (x2)

1. Nanh2 2. Ch3ch2ch2br (or any addition)

cl2 / light

hbr/ peroxide

hbr

NBS / hv, ccl4

1. NBS, hv, ccl4 / 2. KOH

HX / ether, 0C

SOCl2/pyridine

PBr3/ether

mg/ether

2 Li / pentane

CuI / ether

pd(PPh3)4/caco3, thf
