Orgo Reactions

reduces an alkene or an alkyne to an alkane

H2 / Pt

Bromine addition from an alkene, mark, carbocation intermediate, not stereospecific

HBr

Bromine addition to antimark side, OH addition to mark side of alkene, bridged intermediate, anti

Br2 / H2O

Anti addition of two Bromines to alkene, bridged

Br2 / CH2Cl2

Carbocation intermediate, rearrangements, mark addition of OH to an alkene, anti

H2O / H2SO4

Mark addition of an OH to an alkene, no rearrangements, bridged intermediate, anti

1. Hg(OAc)2, H2O / 2. NaBH4, H2O

Antimark addition of OH to an alkene, no shifts, syn

1. BH3, THF / 2. NaOH, H2O2, H2O

splits the double bond into aldehydes and ketones

O3 / (CH3)2S

syn addition of two OHs to a double bond

OsO4 / H2O2, H2O

Forms a triple bond between two vicinal bromines

1. NaNH2, NH3 / 2. H2O

Elongates an alkyne by one Carbon

1. NaNH2, NH3 / 2. CH3Br

Reduces alkyne to a trans alkene

Na (radical) / NH3(l)

Reduces alkyne to a cis alkene

H2 / Lindler’s

Adds an O double bond to the mark side of an alkyne

HgSO4 / H2SO4, H2O

Adds an O double bond to the anti-mark side of an alkyne

1. HB(sia)2, THF / 2.NaOH, H2O2, H2O

adds an mark Br to an alkane

Br2 / Hv

adds a Br to the anti-mark side of a double bond

HBR / ROOR

adds a Br to the allylic position that forms the most stable alkene with a radical, not stereospecific

NBS / delta

Bulky base that forces an unfavorable alkene

LDA

Small, strong base used to form a double bond from a bromine

NaOH / H2O, heat

Replacing an alcohol with a Br with a carbocation intermediate and not stereospecific

HBr

Turns a 2nd or 1st degree OH into a Br with a back attack and no rearrangements

PBr3

Converts 1st and 2nd degree alcohols to Cl without rearrangements and inverted stereochemistry

SOCl2 / pyridine

Dehydrates an alcohol into the most stable double bond

H2SO4 / heat

Takes two vicinal alcohols and makes the more substituted one into a double bonded O

H2SO4 / heat

In the presence of water: Oxidizes 1st degree alcohols into carboxylic acids and 2nd degree alcohols into ketones

H2CrO4

In the absence of water: Oxidizes 1st degree alcohols into carboxylic acids and 2nd degree alcohols into ketones

PCC / CH2Cl2

Splits the single bond between two CIS vicinal alcohols and each form ketones or aldehydes

HIO4