Chapter 7

Question 1

EWG

Answer 1

oxygen

stabilizes anions

easy to remove when bonds weaken

Question 2

Why is aldehyde more acidic

Answer 2

has less EDG than ketones

Question 3

Why are aldehydes more nucleophilic

Answer 3

has less sterics

Question 4

enol

Answer 4

C=C and alcohol

Question 5

tautomers

Answer 5

isomers, differ in placement of protons and double bond

keto is favored over Enol

Question 6

enolate

Answer 6

depronate alpha carbon by base

form carbocation which is a good nu

then carbocation attacks another carbonyl

Question 7

2 enolates of ketones

Answer 7

kinetic and thermodynamic

kinetic is rapid with double bond as less substituted

thermo is slow and stable with double bond at more sub

Question 8

when is kinetic product favored

Answer 8

rapid, irreversible, low temp, strong base with sterics

Question 9

enamine

Answer 9

tautomer of imine

move hydrogen and a double bond

Question 10

imine vs enamine structure

Answer 10

enamine has c=c

imine has N=c (thermodynamic)

Question 11

aldol condensation

Answer 11

aldehyde or ketone is electrophile and nucleophile is enol

forms C-C bond between alpha and beta carbon

removes one carbonyl