Carbonyl Groups: Aldehydes and Ketones

Question 1

carbonyl group electronegativity

Answer 1

e- pulled towards O, C attacked by nucleophiles

Question 2

carbon nucleophilic addition

Answer 2

nucleophile attacks C
+H2O work up

Question 3

carbon nucleophilic addition
- nucleophile and products

Answer 3

K+-C=_N (->nitride)
Na+-C=_CH (->alkyne)

Question 4

water nucleophilic addition

Answer 4

H2O (-> diols)
steps reversible
O attacks C
proton transfer

Question 5

alcohol + aldehyde/ketone = ?

Answer 5

acetal

Question 6

what is connected to the carbon and what is connected to the two os in an acetal?

Answer 6

aldehyde/ketone connected to the carbon (plus H etc)
alcohol connected to either o

Question 7

acetal mechanism

Answer 7

H3O+, H of OH of alcohol joins O of carbonyl, O and everything else joins C
H3O+, another alcohol, make even
*everything reversible

Question 8

nitrogen nucleophiles and aldehyde/ketone

Answer 8

remove H2O
-O from carbonyl, H2 from nucleophi;e
- replace =O with =N(and whatever is attached)

Question 9

esterification + ester naming

Answer 9

carboxylic acid + alcohol -> ester
- carb acid name to main part
- alcohol name to alkyl sub group

Question 10

esterification
- reagent(s)

Answer 10

H3O+

Question 11

esterification
- mechanism

Answer 11

• =O in carb acid attacks H in H3O+
• O in alcohol attacks C of C=O- proton transfer
• proton transfer
• O remakes double bond
• H2O attacks OH+
  *all reversible

Question 12

ester base hydrolysis

Answer 12

ester -> carboxylic acid + alcohol

Question 13

ester base hydrolysis
- reagent(s)

Answer 13

NaOH (gives alcohol + carb acid salt)
H3O+ (gives carb acid)

Question 14

ester base hydrolysis
- mechanism

Answer 14

• NaOH attacks C
• double bond back
• O- takes H
  salt and alcohol formed
• H3O +
  carb acid formed

Question 15

ester reduction

Answer 15

3. ester -> 2. aldehyde + alcohol -> 1. alcohols