alcohol reactions

PCC, CH2Cl2 (dichloromethane)

conversion of a primary alcohol to an aldehyde

Na2Cr2O7, H2SO4, H2O

conversion of a primary alcohol to a carboxylic acid

PCC, CH2Cl2 (dichloromethane)

conversion of a secondary alcohol to a ketone

SOCl2, pyridine

nucleophilic substitution of an alcohol involving chlorine

HBr

nucleophilic substitution of an alcohol involving Br

concentrated H2SO4, heat

dehydration of alcohol to alkene (simple)

1) TsCl, pyridine, 2) NaOEt

dehydration of tertiary alcohol to alkene involv chlorine

NaBH4, EtOH, MeOH or H2O

reduction of an aldehyde or ketone to an alcohol (less reactive one)

LiAlH4, Et2O

reduction of an aldehyde or ketone to an alcohol (more reactive one)

H2, Pt, Pd, or Ni reduces both the carbonyl and double bond

reduction of an aldehyde or ketone to an alcohol (most reactive one)

NaOH (strong nucleophile), SN2

primary substrate substitution to an alcohol

weak nucleophile (H2O), SN1

tertiary substrate substitution to an alcohol

dilute H2SO4

conversion of an alkene to an alcohol (addition, Markov)

1) BH3 .THF, 2) H2O2 hydrogen peroxide, NaOH

conversion of an alkene to an alcohol (addition, anti Markov)

alkyl halide R-X, Mg, Et2O makes R-Mg-X

generating grignard reagent

alkyl halide R-X, Li (2eq) makes R-Li, Li-X

generating organolithium reagents

alkyl halide R-X, Li (2 eq), CuX (0.5 eq) makes R2CuLi

generating Gilman reagent

ZnCu, CH2I2, Et2O

simmons smith, conversion of alkene to cyclopropyl group

CHCl3, t-BuOk

carbenoid with chloroform, conversion of alkene to cyclopropyl with chlorine

alcohol

grignard reagent plus aldehyde or ketone generates

RMgX (2 eq), H2O

what plus ester will generate an alcohol?

protecting groups: 1) TMS-Cl, Et3N (base), 2) Grignard reaction (Mg, aldehyde/ketone, Et2O or H2O), 3) H3O+ or TBAF

reagents for when you have halide and alcohol in same molecule

PCC, CH2Cl2

primary alcohol with what reagent will make an aldehyde?

1) O3, 2) DMS

alkene to aldehyde (ozonolysis) reagents?

1) (Sia)2BH2, 2) H2O2, NaOH generates anti Markovnikov

alkyne to aldehyde (hydroboration) reagents?

PCC, CH2Cl2

secondary alcohol plus what reagents generates a ketone?

1) O3, 2) DMS

alkene with all r groups to ketone reagents (ozonolysis)?

H2SO4, H2O, HgSO4

alkyne to ketone reagents (oxymercurization)