Register to reply

PCl5 / SOCl2 and carboxylic acids

by trollcast
Tags: acids, carboxylic, pcl5, socl2
Share this thread:
trollcast
#1
Nov28-13, 10:50 AM
PF Gold
trollcast's Avatar
P: 291
In my chemistry notes it gives the equations,

##R-COOH + PCl_5 \rightleftharpoons R-COCl + POCl_3 + HCl##

##R-COOH + SOCl_2 \rightleftharpoons R-COCl + SO_2 + HCl##

It then says that in an open system the reaction with thionyl chloride will go to completion as all the products except the acyl chloride can escape as they are gases, so the equilibrium keeps moving right. However why does the reaction with PCl5 not go to completion since the HCl will escape as its a gas?
Phys.Org News Partner Chemistry news on Phys.org
Chemists create nanofibers using unprecedented new method
Nanostructured metal-oxide catalyst efficiently converts CO2 to methanol (w/ Video)
Researchers discover low-grade nonwoven cotton picks up 50 times own weight of oil
monodisperse
#2
Dec9-13, 04:47 AM
P: 5
Quote Quote by trollcast View Post
In my chemistry notes it gives the equations,

##R-COOH + PCl_5 \rightleftharpoons R-COCl + POCl_3 + HCl##

##R-COOH + SOCl_2 \rightleftharpoons R-COCl + SO_2 + HCl##

It then says that in an open system the reaction with thionyl chloride will go to completion as all the products except the acyl chloride can escape as they are gases, so the equilibrium keeps moving right. However why does the reaction with PCl5 not go to completion since the HCl will escape as its a gas?
Phosphoryl chloride is a liquid, ergo....

In reality we as a base, usually triethylamine, to these reactions and perform them under schlenk condition.


Register to reply

Related Discussions
Orgo - Carboxylic acids Biology, Chemistry & Other Homework 0
Carboxylic acids Biology, Chemistry & Other Homework 1
Naming Carboxylic Acids Biology, Chemistry & Other Homework 3
Carboxylic acids Biology, Chemistry & Other Homework 4
Question on the rxn of Alcohol and Carboxylic acids. Chemistry 2