Alcohol Reaction

H₂, Pt on ketone

forms secondary alcohol

H₂, Pt on aldehyde

forms primary alcohol

NaBH₂ on ketone

makes secondary alcohol

NaBH₂ on aldehyde 

makes primary alcohol 

LAH on ketone

makes secondary alcohol

LAH on aldehyde

makes primary alcohol

LAH on carboxcylic acid

makes primary alcohol

LAH on ester 

removes doubled bonded O

LAH on amide

removes double bonded O

grinard preparation

add Mg and ether solvent to Br or Cl (most often Br) 

creates R-MgBr

gringnard reaction 

adds R and OH to location of the doubled bonded O 

gringnard on ketone

makes tertiary alcohol

gringnard on aldehyde

makes secondary alcohol

gringnard on formaldehyde

makes primary alcohol

gringnard on ester 

makes tertiary alcohol 

HCl, ZnCl₂ on OH

swaps OH for Cl

TsCl, pyridine on OH

swaps OH for OTs for Nuc attack

overall inversion of stereochemistry

SOCl₂, pyridine on OH 

swaps OH for Cl for Nuc attack 

overall retention of stereochemistry 

PBr₃ on OH

swaps OH for Br for Nuc attack

overall retention of stereochemistry

CrO₃, H₂SO₄, H₂O on primary OH

makes carboxylic acid

CrO₃, H₂SO₄, H₂O on secondary OH

makes ketone

PCC on primary OH 

makes aldehyde

PCC on secondary OH

makes ketone