Nucleophilic addition at carbonyl groups

Question 1

What is the effect of an electron-withdrawing group on a carbonyl?

Answer 1

Intensifies the positive charge at the carbon, destabilizing the carbonyl (more likely to undergo nucleophilic addition)

Question 2

What can you do to a acetal or imine/enamine to push towards products?

Answer 2

Remove water

Question 3

How can acetals, Imines, and examines be turned back into carbonyls?

Answer 3

Hydrolysis using aq acid

Question 4

a,b-unsaturated carbonyls undergo what kins of addition with strongly basic nucleophiles like Grigs and organolithiums?

Answer 4

1,2-additions (kinetic product)

Question 5

a,b-unsaturated carbonyls undergo what kins of addition with weakly basic nucleophiles like organocuprates and halogens?

Answer 5

1,4-additions

Question 6

What is the effect of conjugation on nucleophilic addition?

Answer 6

Slows reaction b/c it stabilizes the carbonyl

Question 7

Of the reducing agents NaBH4 and LiAlH4, which is strong enough to reduce esters and carboxylate acids?

Answer 7

LiAlH4