Reaction mechanisms Flashcards
(20 cards)
Starting: Alcohol
(COCl)2 in DMSO?
AKA?
Alcohols to aldehydes and keytones.
Swern
Starting: Alcohol
[CrO3Cl-] + [C5H5NH+] in CH2Cl2
AKA?
Alcohols to aldehydes and keytones
AKA PCC
Starting: Alcohol
PBr3
Alcohol to bromine
Starting: Alcohol
SOCl2 with pyridine?
Alchohol to chlorine
Starting: Alcohol
ZnCl2 in HCl
Alcohol to chlorine
Starting: Alcohol
LiCl in DMF
Chlorine via SN2 - inversion!
Starting: Alcohol
MsCl, TsCl, or TfCl
Sulfonate ester; makes excellent LG
Starting: Alcohol
t-BDMS-Cl in NEt3
tert-butyldimethylsilylchloride; protection
Starting: Alcohol
KMnO4
Carboxylic acid on terminal alcohols or carbonyl group for all other alcohols.
Starting: alcohol
Cr6 in acetone
Carboxylic acid on terminal alcohols or carbonyl group for all other alcohols.
m-CPBA in CH2Cl2
epoxidation of alkenes (non-terminal alkenes!!)
Starting with an ester:
NaBH4 with MeOH
No reaction - too weak against esters
Starting with a keytone or an aldehyde:
NaBH4 with MeOH
Where do the protons come from?
alcohol
Alcohol = sodium borohydride
Hydrogenated carbons = methanol
Starting with an aldehyde or keytone:
LiAlH4
Where do the protons come from?
alcohol.
Alcohol = protic solvent (H2O, H3O+, etc)
On hydrogenated carbons = lithium aluminum hydrides
Starting with an ester or carboxylic acid:
LiAlH4
Where do the protons come from?
One alcohol (terminal alcohol on carboxylic acid is lost)
Alcohol = protic solvent (H2O, H3O+, etc)
On hydrogenated carbons = lithium aluminum hydrides
Starting with an ester:
- R-MgBr
- Acid (H3O+)
Aka?
Alcohol with two R groups
Grignard reagents
Starting with an ester or a keytone:
- R-MgBr
- Acid
Aka?
An alcohol and one R group
Grignard
Starting with an ester:
- Li-R
- acid
Alcohol and two R groups
Starting with an aldehyde:
- Li-R
- Acid
Alcohol with one R group
Ethers can be cleaved with?
HI or HBr (HCl and HF are too weak)
