WashU Organic Chemistry 1 Mechanism

primary alcohol + Jones

carboxylic acid

primary alcohol + PCC, CH2Cl2

aldehyde

primary alcohol + DMSO, COCl2

aldehyde

primary alcohol + CH3I

alkoxide

secondary alcohol + Jones

ketone

secondary alcohol + CuO and heat

ketone

secondary alcohol + PCC, CH2Cl2

ketone

secondary alcohol + DMSO, COCl2

ketone

secondary alcohol + H2SO4

alkene

secondary alcohol + acid

ester

secondary alcohol + SOCl2 (retention)

halide

secondary alcohol + PX3 (inversion)`

halide

secondary alcohol + MCPBA

epoxide

alkene + HBr

more substituted bromide

alkene + HBr, ROOR

less substituted bromide

alkene + H3O+

more substituted alcohol

alkene + 1)Hg(OAc)2 and H2O 2)NaBH4

more substituted alcohol

alkene + 1) BH3 THF 2) H2O2 and NaOH

less substituted alcohol

alkene + X2

trans dihalide

alkene + X2 H2O

trans halohydrin (OH on more substituted carbon)

alkene + H2, Pd

alkane

alkene + Zn(Cu), CH2I2

cyclopropane

alkene + CH2N2

cyclopropane

alkene + CHX3, H2O, KOH

cyclopropane with halogen substitutes

alkene + MCPBA

epoxide

alkene + MCPBA, H2O

trans diol

alkene + 1) OsO4 2)H2O2 or H2O

cis diol

alkene + cold dilute KMnO4, NaOH, H2O

cis diol

alkene + warm concentrated KMnO4

ketone and carboxylic acid

alkene + 1)O3 2)DMS

ketone and aldehyde

alkene + 1)OsO4 2) H2O2 3) HIO4

ketone and aldehyde

alkyne + H2 Pd

alkane

alkyne + H2 Pd BaSO4 quinoline

cis alkene

alkyne + Na/NH3

trans alkene

alkyne + X2

trans halogenated alkene

alkyne + HBr

brominated alkene

alkyne + Sia2BH, H2O2, NaOH

aldehyde

alkyne + HgSO4, H2SO4, H2O

ketone

alkyne + KMnO4, H2O, neutral

diketone

alkyne + 1)O3 2)H20

carboxylic acids

alkyne + Hg(OAc)2, H2O

ketone

carbonyl + MgX

alcohol

ketone or aldehyde + NaBH4

alcohol

ketone, aldehyde, acid, ester + LAH

alcohol

epoxide + R-MgX, ether, H3O+

primary alcohol

epoxide + H3O+

trans diol

terminal double bond + warm concentrated KMnO4

ketone, CO2, H2O

dibrominated alkane + 1) NaNH2 at 150 2)H2O

terminal alkyne

dibrominated alkane + KOH fused at 200

internal alkyne

terminal alkyne + NaNH2

acetylide ion

terminal alkyne + HX

more substituted alkene

terminal alkyne + HX, ROOR

less substituted alkene

terminal alkyne + KMnO4, H2O neutral

diketoacid

alcohol + 1) Na 2) R-X

ether

2 primary alcohols + H3O+

ether

ether + HX

two halides

R-S+ R-X

sulfide

alkene + 1) Cl2, H2O 2) NaOH

epoxide