Acylation

What are Acyl Chlorides?

A derivative of carboxylic acids, where the -OH group is replaced by a -Cl group

How do you name Acyl Chlorides?

-oyl chloride e.g. ethanoyl chloride

-Name from the longest carbon chain

What 4 substances do Acyl Chlorides react with and what is an observation they all share in common?

-Water, Ammonia, Alcohol, Primary Amines

-It is a vigorous reaction producing white misty HCl fumes

What is the Word Equation for the reaction between an Acyl Chloride and Alcohol?

Acyl Chloride + Alcohol → Ester + HCl

What is the Word Equation for the reaction between an Acyl Chloride and Water?

Acyl Chloride + Water → Carboxylic Acid + HCl

What is the Word Equation for the reaction between an Acyl Chloride and Ammonia

Acyl Chloride + Ammonia → Amide + HCl

What is the Word Equation for the reaction between an Acyl Chloride and a Primary Amine?

Acyl Chloride + Primary Amine → N-substituted Amine + HCl

What is an N-Substituted Amine?

-Amines that have one or more of their hydrogen atoms replaced by an alkyl group

What are Acid Anhydrides?

-Molecule made by two identical carboxylic acids

Acid Anhydrides react with the same 4 substances Acyl Chlorides react with. What is the common product across all 4 reactions?

-Ethanoic acid

What reaction mechanism do Acyl Chlorides undergo and what is featured in it?

-Nucleophilic Addition-Elimination reactions

-Addition of a Nucleophile on C=O

-Elimination of of small molecule(eg HCl or H₂O

How is aspirin produced?

-Ester made by reacting ethanoic anhydride/ethanoyl chloride with salicylic acid

Why is ethanoic anhydride used in manufacturing of aspirin rather than ethanoyl chloride?

-Less corrosive

-Safer, as:

-Reacts less vigorously with water

-Produces ethanoic acid as by-product instead of harmful HCl gas