26.5- ACYLATION

Question 1

What is acylation?

Answer 1

process by which acyl group introduced into another molecule

Question 2

What do all acid derivates have?

Answer 2

acyl group as part of their structure

Question 3

What are acid derivatives derived from?

Answer 3

carboxylic acids

Question 4

Is the carbonyl group of an acid derivative polar?

Answer 4

yes

Question 5

What is the carbonyl group of an acid derivative attacked by and what happens?

Answer 5

nucleophiles at C𝛿+ and in this process nucleophiles replaces Z and so nucleophile acquires an acyl group
so nucleophile acylated

Question 6

What are the three factors that affect how readily the reaction between an acid derivate and nucleophile happen?

Answer 6

magnitude of 𝛿+ charge on carbonyl carbon, which in turn depends on electron-releasing or attracting power of leaving group

how easily leaving group lost

how good nucleophile is

Question 7

What do the leaving groups of acyl chlorides + acid anhydrides to electrons?

Answer 7

withdraw electrons from carbonyl groups

Question 8

As the leaving group of acyl chlorides + acid anhydrides withdraw electrons from the carbonyl carbon, what does this do?

Answer 8

makes carbon more positive + makes these compounds reactive towards nucleophiles

Question 9

Are acyl chlorides + acid anhydrides good or bas acylating agents?

Answer 9

goof acylating agents

Question 10

What is the reactivity of acyl chlorides like in comparison to acid anydrides?

Answer 10

acyl chlorides somewhat more reactive than acid anhydrides

Question 11

What must nucleophiles have?

Answer 11

have lone pair of electrons which they use to attack electron-deficient carbon C𝛿+

Question 12

What are the best nucleophiles?

Answer 12

ones that are best at donating their lone pair

Question 13

What nucleophiles with acyl chlorides + acid anhydrides react with in order of reactivity? (highest to lowest)

Answer 13

primary amine
ammonia
alcohol
water

Question 14

What is the reaction of acid derivates (acyl chlorides + acid anhydrides) and nucleophiles called?

Answer 14

addition-elimination reactions

Question 15

As the all the nucleophiles are neutral in the reaction between an acid derivate and nucleophile, what must the nucleophiles do?

Answer 15

lose hydrogen ion during reaction

Question 16

If the nucleophile is ammonia and reacts with an acid derivative, what is produced?

Answer 16

amide

Question 17

If the nucleophile is a primary amine and reacts with an acid derivate, what is produced?

Answer 17

N-substitutes amide

Question 18

If the nucleophile is the -OH group of an alcohol and reacts with an acid derivate, what is produced?

Answer 18

ester

Question 19

If the nucleophile is OH from water and reacts with an acid derivate, what is the product?

Answer 19

carboxylic acid

Question 20

What are the advantages of ethanoic anhydride over ethanoyl chloride as an acylating agent? (4)

Answer 20

cheaper
less corrosive
doesn’t react with water as readily
safer, as by-product of its reaction is ethanoic acid rather than hydrogen chloride

Question 21

What is one important use of ethanoic anhydride?

Answer 21

production of aspirin