Devise a simple synthetic route to an amide from a carboxylic acid. Give a mechanism for the final step and explain why the reagents are not added 1:1 in the final step

1st step: SOCl2 or PCl3 to form an acyl chloride, which is now significanlty more electrophilic based on leaving gorup abiliity, hence an amine can now attack the acyl chloride to form the amide, where as adding an amine and a carboxylic acid would have just completed proton transfer.

2nd step: RNH2. Mechanism to be drawn on board, attack the carbonyl, remove proton, kick out chloride.

Problems with final step is that the conversion will create HCl in situ, which will acidifiy the base and make it an inert nucleophile, so add excess of amine to remove the HCl

Answered by Elliot B. Chemistry tutor

1885 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Which is more reactive, an alkane or an alkene and why?


The enthalpy of combustion of ethanol is −1371 kJ mol−1 . The density of ethanol is 0.789 g cm−3 . Calculate the heat energy released in kJ when 1 dm3 of ethanol is burned.


Explain, with reference to the electronic transitions involved, how characteristic flame colours of metal ions are formed and why the flame colours are different.


2-chloropropanoic acid has a Ka of 1.48E-3. Write an expression for Ka and hence or otherwise, calculate the pH of a 0.35M solution of 2-chloropropanoic acid


We're here to help

contact us iconContact usWhatsapp logoMessage us on Whatsapptelephone icon+44 (0) 203 773 6020
Facebook logoInstagram logoLinkedIn logo
Cookie Preferences