9: Acyl Chlorides Flashcards
What is the functional group of acyl chlorides?
COCl
What is produced when acyl chlorides react with water?
Carboxylic acid and HCl
How do acyl chlorides react with cold water?
Vigourously
How do acyl chlorides react with alcohols?
Vigorously at room temperature
What is produced in a reaction with acyl chlorides and alcohol?
Ester + HCl
Which is a quicker method of producing an ester? Esterification or reaction of acyl chlorides with alcohol?
Reaction of acyl chloride with alcohol
What is produced when acyl chlorides react with ammonia at room temperature?
Amide and HCl
How do acyl chlorides react with ammonia at room temperature?
Vigourously
What is produced when primary amines react with acyl chlorides?
N-substituted amides and HCl
How do acyl chlorides react with primary amines at room temperature?
Vigourously
Name the mechanism used when an acyl chloride reacts with either ammonia, primary amine, alcohol or water.
Nucleophilic addition-elimination
In the 1st step of nucleophilic addition-elimination, what happens?
Nucleophile adds onto the acyl chloride and the Cl- ion gets displaced.
In the 2nd step of nucleophilic addition-elimination, what happens?
The hydrogen on the nucleophile leaves to create an acyl chloride derivative
Why is the carbon in the 1st step of nucleophilic addition-elimination easily attacked?
The carbon is slightly positive and the nucleophile is negative, therefore it attracts.
In the 1st step of nucleophilic addition-elimination, where are the pair of electrons in the double bond transferred to?
Onto the oxygen, breaking the double bond
In the 1st step of nucleophilic addition-elimination, how is the Cl removed?
The double bond between oxygen and carbon reforms and the Cl- ion is kicked off.
What is the product of the first step of nucleophilic addition-elimination?
A positively charged ion with the nucleophile attached and a :Cl-
In the 2nd step of nucleophilic addition-elimination, electrons transfer onto the nucleophile from where?
The bond between the hydrogen and nucleophile.
What are acid anhydrides made from?
2 identical carboxylic acids
What molecule is eliminated when 2 carboxylic acids join to form an acid anhydride?
H2O
Which reactions are more vigourous - acid anhydrides or acyl chlorides?
Acyl chlorides
What organic molecule makes up aspirin?
Esters
Name the 2 molecules used to produce aspirin.
Salicylic acid (has an OH group) and ethanoic anhydride
Why is ethanoic anhydride used in industry? Give 4 reasons.
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
