Mechanisms reagents and solvents Flashcards
Ketone to cyanohydrin R&S
R = NaCN, H2SO4
S = water
Cyanohydrin to ketone R&S
R = NaOH acid catalyst
S = H2O
Ketone to secondary alcohol R&S
R = NaBH4
S = EtOH
Ketone to tertiary alcohol R&S
R = MeMgBr/ LiMe, H2O step 2 only
S = Et2O/ THF (aprotic)
ketone to hydrate R&S
R = H2O
S = H2O
Ketone to hemiacetal R&S (acidic and basic)
R = MeOH ( with either HCl/ NaOH)
S = MeOH
Hemiacetal to ketone R&S (acidic and basic)
R = H2O (with either HCl or NaOH)
S = H2O
Bisulfide addition of a ketone R&S
R = NaHSO3 (sodium bisulfite)
S = H2O
Hemiacetal to acetal R&S
R = MeOH (HCl catalyst needed to protonate leaving group)
S = THF
Acetal to ketone R&S
R = H2O (HCl catalyst)
S = THF
Acid chloride to ester R&S
R = EtOH and base eg pyridine
S = THF
Ester to carboxylic acid R&S (acidic and basic)
R = H2O (HCl or NaOH catalyst)
S = H2O
Acid chloride to acid anhydride R&S
R = sodium ethanoate
S = THF
Acid chloride to amide R&S
R = NH3
S = H2O
Amide to carboxylic acid R&S (acidic or basic)
R = H2O, Heat (HCl/NaOH cat )
S = H2O
Amide to amine R&S
R = LiAlH4
S = Et2O/ THF (aprotic)
Carboxylic acid to acid chloride R&S (two possible reactions)
R = SOCl2
S = none
or
R = PCl5
S = THF
Amide to ketone R&S
R = MeMgBr (H2O step 2 & HCl)
S = Et2O/THF
Nitrile to ketone R&S
R = RMgBr acid catalyst
S = Et2O/THF
Ketone to imine R&S
R = NH3 (HCl catalyst)
S = THF
Ketone to alkene R&S
R = phosphonium ylide
S = Et2O (aprotic)
Ketone to enol R&S
R = H2O (acid/ base catalyst)
ketone to alkyl bromide R&S
R = Br2 and acetic acid AcOH
Ketone to ketone with R group added R&S
step one
R = LDA
S = THF
step 2
R = R-I
Aldehyde to aldol R&S
R = NaOH
S = H2O
