Alcohols Flashcards

0
Q

TsCl, pyridine

A

Tosylate (OTs)

Notes: Sn2, retains original stereochemistry, 3 prime sulfonate ethers are very unstable

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

TfCl, pyridine

A

Triflate (OTf)

Notes: Sn2, retains original stereochemistry, 3 prime triflate ethers are very unstable

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

SOCl2, pyridine

A

Chloride

Notes: Sn2, reaction occurs because of Le Chatelier’s Principle, stereochemistry reversed

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

PBr3

A

Bromide

Notes: Sn2, stereochemistry reversed, irreversible

How well did you know this?
1
Not at all
2
3
4
5
Perfectly