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1 PCC CH2Cl2

O3 CH2Cl2 Me2S

LAH 1

LiAlH(OtBu)3

DIBALH H2O

LiAlH(OtBu)3

Et2O RCOCl

DIBALH RCO2R

RCN

SOCl2

1

OH

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OR H

H2CrO4 PCC CH2Cl2 2

PBr3 OH Br

DIBALH

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OH OR

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OR

HCl

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H3O+

HCl

H3O+

H2O

RSH HA

HSRSH BF3

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H2

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OH CN

HCN

C6H5Li

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1 2 P(C6

H5)3 P+(C

6H5)3

RLi

(E)

(RO)3

P

KMnO4 OH

Ag2O OH

H3O+

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O3 H2O2

H2CrO4 1

CO2 H3O+

SOCl2

PCl3

PCl5

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NaOH

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1 2

1 2

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1 2

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H2 PdC HBr CH3CO2H

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RNCO

CO2

CO2

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LDA

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RO

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2

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