9: Acyl Chlorides

Question 1

What is the functional group of acyl chlorides?

Answer 1

COCl

Question 1

What is produced when acyl chlorides react with water?

Answer 1

Carboxylic acid and HCl

Question 2

How do acyl chlorides react with cold water?

Answer 2

Vigourously

Question 3

How do acyl chlorides react with alcohols?

Answer 3

Vigorously at room temperature

Question 4

What is produced in a reaction with acyl chlorides and alcohol?

Answer 4

Ester + HCl

Question 5

Which is a quicker method of producing an ester? Esterification or reaction of acyl chlorides with alcohol?

Answer 5

Reaction of acyl chloride with alcohol

Question 6

What is produced when acyl chlorides react with ammonia at room temperature?

Answer 6

Amide and HCl

Question 7

How do acyl chlorides react with ammonia at room temperature?

Answer 7

Vigourously

Question 8

What is produced when primary amines react with acyl chlorides?

Answer 8

N-substituted amides and HCl

Question 9

How do acyl chlorides react with primary amines at room temperature?

Answer 9

Vigourously

Question 10

Name the mechanism used when an acyl chloride reacts with either ammonia, primary amine, alcohol or water.

Answer 10

Nucleophilic addition-elimination

Question 11

In the 1st step of nucleophilic addition-elimination, what happens?

Answer 11

Nucleophile adds onto the acyl chloride and the Cl- ion gets displaced.

Question 12

In the 2nd step of nucleophilic addition-elimination, what happens?

Answer 12

The hydrogen on the nucleophile leaves to create an acyl chloride derivative

Question 13

Why is the carbon in the 1st step of nucleophilic addition-elimination easily attacked?

Answer 13

The carbon is slightly positive and the nucleophile is negative, therefore it attracts.

Question 14

In the 1st step of nucleophilic addition-elimination, where are the pair of electrons in the double bond transferred to?

Answer 14

Onto the oxygen, breaking the double bond

Question 15

In the 1st step of nucleophilic addition-elimination, how is the Cl removed?

Answer 15

The double bond between oxygen and carbon reforms and the Cl- ion is kicked off.

Question 16

What is the product of the first step of nucleophilic addition-elimination?

Answer 16

A positively charged ion with the nucleophile attached and a :Cl-

Question 17

In the 2nd step of nucleophilic addition-elimination, electrons transfer onto the nucleophile from where?

Answer 17

The bond between the hydrogen and nucleophile.

Question 18

What are acid anhydrides made from?

Answer 18

2 identical carboxylic acids

Question 19

What molecule is eliminated when 2 carboxylic acids join to form an acid anhydride?

Answer 19

H2O

Question 20

Which reactions are more vigourous - acid anhydrides or acyl chlorides?

Answer 20

Acyl chlorides

Question 21

What organic molecule makes up aspirin?

Answer 21

Esters

Question 22

Name the 2 molecules used to produce aspirin.

Answer 22

Salicylic acid (has an OH group) and ethanoic anhydride

Question 23

Why is ethanoic anhydride used in industry? Give 4 reasons.

Answer 23

It is cheaper than ethanoyl chloride (an acyl chloride)
Its safer and less corrosive
It reacts more slowly with water
Does not produce dangerous hydrogen chloride fumes