Chapter 8: 8.2 Alcohols as Nucleophiles and Electrophiles

Question 1

Are alcohols good nucleophiles/electrophiles?

Answer 1

In their -OH form, they are neither good nucleophiles nor good electrophiles

Question 2

What must happen to an alcohol to make it a good nucleophile?

Answer 2

It needs to become deprotonated by addition of a stronger base (pKa > ~ 18) to form an alkoxide

Question 3

What must happen to an alcohol to make it into a good electrophile (leaving group)?

Answer 3

Needs to be converted to another functional group

Question 4

To become a good electrophile:

What can an alcohol be converted to? Through what process?

Answer 4

1. Water, through protonation
2. Tosyl group, through tosylation
3. Mesyl group, through mesylation
4. An alkyl halide (R-X), with treatment with HX (strong acid)