Carboxylic Acids Flashcards

Flashcards about Carboxylic Acids

Carboxylic acids

Organic acids characterized by the presence of at least one carboxyl group.

General formula of a carboxylic acid

R-COOH

Carboxyl group (or carboxy)

A functional group consisting of a carbonyl (RR'C=O) and a hydroxyl (R-O-H), with the formula -C(=O)OH or -COOH.

Carboxylic acids as Bronsted-Laury acids

Proton donors and the most common type of organic acid.

Formic acid

H-COOH, occurs in ants.

Acetic acid

CH3-COOH, gives vinegar its sour taste.

Dicarboxylic, tricarboxylic, etc. acids

Acids with two or more carboxyl groups.

Oxalic acid

(COOH)2, two connected carboxyls.

Mellitic acid

An example of a hexacarboxylic acid.

Citric acid

In lemons.

Tartaric acid

In tamarinds.

Carboxylate anion

R-COO-

Naming the carboxylate anion

With the suffix -ate, so acetic acid becomes acetate ion.

IUPAC nomenclature for carboxylic acids

Have an -oic acid suffix (e.g., octadecanoic acid).

Common nomenclature for carboxylic acids

The suffix is usually -ic acid (e.g., stearic acid).

Formic acid chemical formula, common location

HCOOH, Insect stings

Acetic acid chemical formula, common location

CH3COOH, Vinegar

Propionic acid chemical formula, common location

CH3CH2COOH, Preservative for stored grains

Butyric acid chemical formula, common location

CH3(CH2)2COOH, Rancid butter

Valeric acid chemical formula, common location

CH3(CH2)3COOH, Valerian

Caproic acid chemical formula, common location

CH3(CH2)4COOH, Goat fat

Enanthic acid chemical formula

CH3(CH2)5COOH

Caprylic acid chemical formula, common location

CH3(CH2)6COOH, Coconuts and breast milk

Pelargonic acid chemical formula, common location

CH3(CH2)7COOH, Pelargonium

Capric acid chemical formula

CH3(CH2)8COOH

Lauric acid chemical formula, common location

CH3(CH2)10COOH, Coconut oil and hand wash soaps.

Myristic acid chemical formula, common location

CH3(CH2)12COOH, Nutmeg

Palmitic acid chemical formula, common location

CH3(CH2)14COOH, Palm oil

Stearic acid chemical formula, common location

CH3(CH2)16COOH, Chocolate, waxes, soaps, and oils

Arachidic acid chemical formula, common location

CH3(CH2)18COOH, Peanut oil

Solubility of carboxylic acids

Smaller carboxylic acids (1 to 5 carbons) are soluble with water, whereas higher carboxylic acids are less soluble due to the increasing hydrophobic nature of the alkyl chain.

Carboxylic acids with strong odors

Acetic acid (vinegar) and butyric acid (rancid butter).

Chemical properties of acetic acid

Acetic acid reacts with alkalies to form corresponding salts; donates a proton and forms salts with bases.

Important reactions of carboxylic acids with other functional groups.

acyl halide, anhydride, ester, amide, nitrile

Methanoic/Formic acid

An important intermediate in chemical synthesis and occurs naturally in the venom of bee and ant stings.

Aspirin can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetate ion from __

Acetic anhydride or acetic chloride

Oxalic acid

Dicarboxylic acid, 3000 times stronger than acetic acid, present in many plants and animals.

Naturally occurring esters

Most naturally occurring esters are colorless, volatile liquids with low molecular weights that are common flavouring agents or pheromones.

Esterification

Formed from the reaction of carboxylic acids and alcohols