Chapter 21

Question 1

The physical properties of acid derivatives depend on their _______ and their _______ properties

Answer 1

polarity
H-bonding
- intermolecular forces

Question 2

Rank alkanes, alcohols, nitriles, esters, amides, and carboxylic acids based on bp
(from highest to lowest)

Answer 2

1) amides
2) carboxylic acids
3) alcohols
3) nitriles
4) esters
5) alkanes

Question 3

_______ and ______ cannot be used in nucleophilic solvents because they can react with them

Answer 3

acid chlorides and anhydrides

Question 4

_______, _______, and _______ are relatively soluble in water due to their high polarity and ability to form H-bonding with water

Answer 4

esters, amides, and nitriles
- frequently used as solvents because they provide a polar medium without OH or NH groups that can react with nucleophiles

Question 5

What are the 4 factors that affect reactivity? and rank them in order of importance

Answer 5

1) LG ability (weak base = better)
2) resonance (bad)
3) sterics (more=bad)
4) inductive effect (EWG=good)

Question 6

In general strong base may serve as a leaving group if it leaves in a highly _______ step

Answer 6

exothermic
- SN2 not exothermic cuz concerted
- acyl substitution is exothermic cuz when OCH3 leaves, it forms a carbonyl making it more stable

Question 7

_______ reactive intermediates can be converted to _______ reactive derivatives
- whether interconversions are allowed

Answer 7

more
less
- more to less is allowed

Question 8

ALL acid derivates _______ (break with H2O) to give _______. under basic or acidic conditions

Answer 8

hydrolyze
carboxylic acid

Question 9

Be careful when hydrolyzing under basic conditions cuz often times, the carboxylic acid will turn into _______

Answer 9

carboxylate

Question 10

Nitriles are hydrolyzed to amides (_______), then further to carboxylic acids (_______)

Answer 10

mild
- room temp
harsh
- reflux
- heat