orgo ch11

oxidation reduction

inc in oxidation number of atom on product side is oxidation and dec in oxidation number of atom on product side is reduction

oxidation

involves carbon atom forming more bonds with oxygen

reduction

involves carbon atom forming more bonds with H

catalytic hydrogenation- alkene —→ H2, Pd-C or Pt or Ni in ethanol or acetic acid

forms alkanes, syn addition, cis form meso and trans form pair of enan

catalytic hydrogenation
alkyne—→ 2H2, Pd-C

complete reduction, alkyne to alkane

catalytic hydrogenation-
alkyne—→ H2, Lindlar’s catalyst

partial reduction, internal alkyne form cis alkene, terminal alkyne form normal alkene

Alkene ——> Na,NH3(I) or Na,NH3,-33C

forms trans alkene, stereospecific

Catalytic hydrogenation-
nitrile and azide ——> H2 + Pd-C

cn form ch2nh2, n3 form nh2, no change in stereochem

nitro group —→ H2 and Pd-C

no2 reduced to nh2

ketones and aldehydes ——> NaBH4, CH3OH

form alcohols, aldehydes form primary oh, ketones form secondary oh

alkenes ——>1. O3, 2.(CH3)2S or H2O2 form what

form ozonide, forms ketones and aldehydes or forms ketones and carboxylic acid

Alkene ——> 1.OsO4, tBuOOH(TBHP), tBuOH, OH

forms Os, forms syndihydroxy compound, stereospecific and stereoselective, cis forms meso and trans form pair of enan

Vicinal dioles ——> HIO4 or NaIO4,H2O

forms ketone or aldehyde

Alkenes ——> MCPBA in CHCl2 or MMPP

forms epoxide, one step reaction, stereospecific, cis form meso and trans form pair of enan

Oxidation of OH= use H2CrO4, H2O, acetone

primary oh form carboxylic acid, secondary oh form ketone

Oxidation of OH= use CrO3, aq H2SO4, acetone

primary oh form carboxylic acid, secondary oh form ketone

Oxidation of OH= use Na2Cr2O7, H2SO4, H2O

primary oh form carboxylic acid, secondary oh form ketone

oxidation of OH= CrO3, pyridine

primary oh form aldehyde

oxidation of OH= PCC in CH2Cl2

primary oh form aldehyde

Oxidation of OH= 1DMSO, COCl2/ 2. Et3N

primary oh form aldehyde, secondary oh form ketone

Oxidation of OH= Use IBX in DMSO

primary oh form aldehyde, secondary oh form ketone

Oxidation of OH= DMP in CH2Cl2

primary oh form aldehyde, secondary oh form ketone

Oxidation of OH= Use MnO2

benzylic oh form ketone, allylic oh form aldehyde