Unit 3.3.9 - Carboxylic acids and derivatives
All documents for this subject (16)
Seller
Follow
ramiriam
Reviews received
Content preview
Acyl Chloride and Acid Anhydride's
Acyl chlorides have the functional group COCl with the general formulae: CnH2n-1OCl.
The name ends with -oyl chloride. They are much more reactive than carboxylic acids and can
react with a range of molecules where Cl is substituted for an oxygen/ nitrogen group and HCl
fumes are given off.
They are produced in a reaction between carboxylic acids + phosphorus (v) chloride --->
phosphorus trichloride + acetyl chloride + hydrochloric acid.
The reactions are nucleophilic addition-elimination reactions.
A lone pair of electrons from ethanol is donated to the + carbon of the ethanoyl chloride. This is
an addition reaction. In the second step of the reaction of HCl molecule is formed by breaking
the O-H bond and formation of a C=O bond. This is an elimination reaction.
Reaction with water
A vigorous reaction, steamy fumes of HCl. Hydrogen chloride can be removed as a gas so a
pure ester is formed.
Reaction with alcohols
Slower and less vigorous so it needs to be warmed.
Reaction with ammonia
Reaction with primary amines
, Nucleophilic addition-elimination reactions have two steps:
1. Nucleophile adds onto the acetyl chloride displacing the Cl- ion.
2. The hydrogen leaves to create an acetyl chloride derivative.
The shorter/smaller chain is next to the N when naming the secondary amide. (N-methyl
ethanamide).
Acylation - replacing a H with an acetyl group (COCH3).
Made from two identical carboxylic acid molecules joined via an oxygen with carbonyl groups
on either side.
The reactions are very similar to acetyl chlorides but are less vigorous and produce a carboxylic
acid instead of HCl.
To name a carboxylic acid the acid part of the name is removed and replaced with
anhydride - ethanoic acid --> ethanoic anhydride.
The benefits of buying summaries with Stuvia:
Guaranteed quality through customer reviews
Stuvia customers have reviewed more than 700,000 summaries. This how you know that you are buying the best documents.
Quick and easy check-out
You can quickly pay through credit card or Stuvia-credit for the summaries. There is no membership needed.
Focus on what matters
Your fellow students write the study notes themselves, which is why the documents are always reliable and up-to-date. This ensures you quickly get to the core!
Frequently asked questions
What do I get when I buy this document?
You get a PDF, available immediately after your purchase. The purchased document is accessible anytime, anywhere and indefinitely through your profile.
Satisfaction guarantee: how does it work?
Our satisfaction guarantee ensures that you always find a study document that suits you well. You fill out a form, and our customer service team takes care of the rest.
Who am I buying these notes from?
Stuvia is a marketplace, so you are not buying this document from us, but from seller ramiriam. Stuvia facilitates payment to the seller.
Will I be stuck with a subscription?
No, you only buy these notes for $4.42. You're not tied to anything after your purchase.