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

EB
Answered by Elliot B. Chemistry tutor

2381 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

(See word doc for complete info) An experiment is carried out whereby the decomposition of hydrogen iodide is observed. Given the equilibrium compositions of each species, calculate the initial mass of hydrogen iodide.


How does free radical substitution work?


Explain why the 2nd Electron aiffinity of Chlorine is Endothermic whilst the first electron affinity is exothermic


What are the three main factors that affect metallic bonding?


We're here to help

contact us iconContact ustelephone icon+44 (0) 203 773 6020
Facebook logoInstagram logoLinkedIn logo

MyTutor is part of the IXL family of brands:

© 2025 by IXL Learning