Alcohols Flashcards
0
Q
TsCl, pyridine
A
Tosylate (OTs)
Notes: Sn2, retains original stereochemistry, 3 prime sulfonate ethers are very unstable
1
Q
Strong Acid (conc. HI, conc. HBr)
A
Alcohol -> Alkyl Halide
Notes: Sn2/Sn1 depending on sterics - watch out for rearrangement and relative nucleophilicity
2
Q
TfCl, pyridine
A
Triflate (OTf)
Notes: Sn2, retains original stereochemistry, 3 prime triflate ethers are very unstable
3
Q
SOCl2, pyridine
A
Chloride
Notes: Sn2, reaction occurs because of Le Chatelier’s Principle, stereochemistry reversed
4
Q
PBr3
A
Bromide
Notes: Sn2, stereochemistry reversed, irreversible