CHAPTER 18: FUNCTIONAL DERIVATIVES OF CARBOXYLIC ACIDS

Background Information for Carboxylic Acids and Derivatives

Nomenclature of Carboxylic Acids and Derivatives

When nitriles are hydrolysed you can think of them reacting with water in two stages - first to produce an amide, and then the ammonium salt of a carboxylic acid.

Carboxylic Acids and Derivatives

The nitrile is heated under reflux with dilute hydrochloric acid. Instead of getting an ammonium salt as you would do if the reaction only involved water, you produce the free carboxylic acid.

If you wanted the free carboxylic acid in this case, you would have to acidify the final solution with a strong acid such as dilute hydrochloric acid or dilute sulphuric acid. The ethanoate ion in the sodium ethanoate will react with hydrogen ions as mentioned above.


Background Information for Carboxylic Acids and Derivatives

Background for Carboxylic Acids and Derivatives
A carboxylic acid contains an hydroxide attached to C of C=O group (carbonyl group). An acid halide contains a halogen attached to the C of the C=O group. An ester contains an alkoxy group attached to a C of a C=O. An anhydride contains two C=O separated by an oxygen. An amide contains a nitrogen attached to C of a C=O. The carbon in the carbonyl is sp2 hybridized, has a bond angle of 120o, and is trigonal planar. Carboxylic acids, primary amides, and secondary amides have intermolecular hydrogen bonding. Carboxylic acids, primary amides, and secondary amides have higher melting points and boiling points than other carboxylic acid derivatives.

Nomenclature of Carboxylic Acids and Derivatives

We report a convenient method for the synthesis of dinorbile acids (23,24-dinor-5β-cholan-22-oic acids, pregnane-20-carboxylic acids) in fair to good yields from norbile acid nitriles in one step by oxidative hydrolysis with oxygen in the presence of potassium-t-butoxide. The method results in stepwise overall removal of two carbon atoms in bile acid side chains in two steps. Dinorbile acids corresponding to several common bile acids have been prepared and their structures confirmed by spectroscopic methods. This simple method for synthesis of dinorbile acids may facilitate their study metabolically.

Carboxylic Acids and Nitriles | Carboxylic Acid | Acid

Uses of Carboxylic Acids and Derivatives
Esters, tertiary amides, and nitriles are used as solvents. Formic acid is in ant bites. Acetic acid is used as vinegar.

The hydrolysis of nitriles to carboxylic acids is efficient

Nomenclature of Carboxylic Acids and Derivatives
In a carboxylic acid, the longest continuous carbon chain is the parent compound. Number the chain so that the C at the C=O is position 1. From the alkyl prefixes, use Aanoic acid.@ Name and number substituents. An acid halide is named as alkanoyl halide. An ester is named as an alkyl alkanoate. An anhydride is named as an alkanoic alkanoic anhydride. An amide is named as an alkanamide.

05/01/2018 · Preparation of Carboxylic Acids ..

Synthesis of Carboxylic Acids
Zero and primary alcohols are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, or chromium trioxide to form carboxylic acids. Aldehydes are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, or chromium trioxide to form carboxylic acids. Alkyl magnesium halide is treated with carbon dioxide, followed by hydrolysis, yields a carboxylic acid. Nitriles are hydrolyzed to yield carboxylic acids.