CA Derivates

Question 1

all CA derivatives are formed from…

Answer 1

condensation rxn w CA, losing water bc of interaction of hydroxyl group w incoming nucleophile

Question 2

how are amides made?

Answer 2

• CA condensation rxn w ammonia or amine, only 1° or 2° amines can will undergo rxn bc loss of H from nu required for this to take place

Question 3

cyclic amides are called…

Answer 3

lactams and named according to the carbon bonded to the nitrogen, the first noncarbonyl carbon is α

Question 4

the bp of amides compared to their CA is…

Answer 4

lower or higher depending on where or not it can H bond

Question 5

how are esters made?

Answer 5

• dehydration synthesis of CA derivatives and alcohols
• fischer esterification: under acidic conditions CA and alcohols condense into esters w water product

Question 6

what are cyclic esters called?

Answer 6

lactones, names the same as lactams

form
aceto
propio
butyro
valero

Question 7

BP of esters compared to original CA

Answer 7

• esters have lower BP bc they can’t H bond

Question 8

triacylglycerols

Answer 8

esters of long chain CA and glycerol

Question 9

saponification

Answer 9

process by which fats are hydrolyzed under basic conditions to produce soap, but additional acidification produces FA

Question 10

how are anhydrides formed?

Answer 10

condensation of dimers of CA

intramolecular condensation forms phyhalic and succinic anhydrides are cyclic anhydrides

certain cyclic anhydrides can be formed by simply heating CA, but only 5 and 6 membered rings can be formed bc it’s driven by stability

Question 11

anhydride bp compared to CA it’s derived from

Answer 11

higher bp on account of weight

Question 12

relative reactivity of CA derivatives and why

Answer 12

1) anhydrides: resonance stabilization (can stabilize a pos charge once nu attack), 3 EWG, and most electrophilic bc of EWG

2) esters: 2 EWG

3) amide: EDG amino group

Question 13

why are lactam and lactones more reactive to hydrolysis?

Answer 13

• contain more strain
• 4 membered rings have torsional strain from eclipsing interactions and sp3 angle compression
• fusion of a second ring inc ring strain, reduced resonance, and inc likelihood of hydrolysis (B-lactam)

Question 14

ammonia + CA or CA deriv

rxn type(s)

Answer 14

amide and CA
nu sub and cleavage

Question 15

alcohol + anhydride

rxn type(s)

Answer 15

ester and CA
nu sub cleavage
only useful with symmetric

Question 16

water + anhydride

rxn type(s)

Answer 16

2 CA
nu sub cleavage
only useful w symmetric

Question 17

ester + alcohol

rxn type(s)

Answer 17

swap OR groups
transesterification, nu sub, hydrolysis

Question 18

water + amide
acidic cond.

rxn type(s)

Answer 18

CA and ammonia
nu sub, cleavage, hydrolysis

Question 19

water + amide
basic cond.

rxn type(s)

Answer 19

carboxylated anion and ammonia
nu sub, cleavage, hydrolysis