University:
The University Of Western Ontario
Course:
2223B | Organic Chemistry of Biological Molecules
Academic year:

2023
Views:

443

Pages:

1
Author:

Cole M

Carboxylic Acids Carboxylic Acid Reactions Overview: Carboxylic Acid Derivatives are those which the OH group is replaced with another functional group Acid chloride (ROCl) is the most reactive of the carboxylic acid derivatives and can be formed using SOCl2, PCl3, or PCl5 Esterification occurs when a carboxylic acid reacts with an alcohol (ROH) catalyzed by H+ - Is known as Fischer Esterification Thioesterification occurs when a thioester is formed when a carboxylic acid reacts with a thiol (RSH) in the presence of an acid Acid anhydride is formed when a carboxylic acid reacts with an acid chloride in the presence of a base In order to generate an amide, you need to use DCC (in order to make sure an acid base reaction doesn’t occur) and an amine “Less reactive” to nucleophilic attack Carboxylic acids will typically have higher boiling points than alcohols of similar molecular weight (same # of carbons) Reduction of Carboxylic Acids: LiAlH4 reduces both ketones and carboxylic acids while BH3 reduces only carboxylic acids Lactones are cyclic carboxylic esters Decarboxylation: The key to decarboxylation is to have a carboxylic acid (or even a carbonyl like a ketone) beta to the carbonyl of the other carboxylic acid (generates CO2) Alpha Substitution of Carboxylic Acids: PBr3 converts the carboxylic acid into an acyl bromide Halogens are better leaving groups than water