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

2895 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Briefly describe the concept of electronegativity and explain why CCl4 is a non-polar molecule


Explain the bonding and thus the properties of a carbon allotrope


explain why the electronegativity of fluorine is greater than that chlorine


Calculate the empirical and molecular formula of the molecule giving rise to the molecular ion peak at 148 m/z. The percentage composition by weight is 64.80 % carbon, 13.62 % hydrogen, and 21.58 % oxygen


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:

© 2026 by IXL Learning