Physical and Bond Properties
Aliphatic monocarboxylic acids have been known for a long time because they are easily obtained from common natural sources. Many of them have trivial names.
▶ Watch the video on YouTube
| Formula R-CO2H | IUPAC Name (... acid) | Trivial name (...acid) | M.P. | B.P. (mm Hg) | Solubility in water (g/L) | Natural source |
|---|---|---|---|---|---|---|
| H | Methanoic | Formic | 8 | 101(763) | unlimited | Ants |
| CH3 | Ethanoic | Acetic | 17 | 118(763) | unlimited | Vinegar (wine) |
| CH3CH2 | Propanoic | Propionic | -21 | 141(763) | unlimited | Dairy products |
| CH3(CH2)2 | Butanoic | Butyric | -5 | 164(763) | unlimited | Rancid butter, cheese |
| CH3(CH2)3 | Pentanoic | Valeric | -34 | 186(763) | 50 | Valerian root |
| CH3(CH2)4 | Hexanoic | Caproic | -3 | 205(763) | 10 | Goats |
| CH3(CH2)5 | Heptanoic | Enanthic | -8 | 223(763) | 2 | Wine |
| CH3(CH2)6 | Octanoic | Caprylic | 17 | 239(763) | 0.7 | Goat butter |
| CH3(CH2)7 | Nonanoic | Pelargonic | 15 | 255(763) | 0.3 | Geranium leaves |
| CH3(CH2)8 | Decanoic | Capric | 32 | 270(763) | 0.2 | Cocoa butter |
| CH3(CH2)10 | Dodecanoic | Lauric | 44 | 299(763) | 0.01 | Laurel leaves |
| CH3(CH2)12 | Tetradecanoic | Myristic | 54 | 251(100) | <0.01 | Nutmeg |
| CH3(CH2)14 | Hexadecanoic | Palmitic | 63 | 267(100) | <0.01 | Palm oil |
| CH3(CH2)16 | Octadecanoic | Stearic | 72 | 183(1) | <0.01 | Cocoa butter |
Aliphatic dicarboxylic acids have also been known for a long time. They are important synthetic intermediates.
| Formula HO2C-X-CO2H | IUPAC Name (...acid) | Trivial name (...acid) | M.P. | Natural source |
|---|---|---|---|---|
| --- | Ethanedioic | Oxalic | 190 | Kidney stones |
| CH2 | Propanedioic | Malonic | 136 | Apples |
| (CH2)2 | Butanedioic | Succinic | 188 | Amber |
| (CH2)3 | Pentanedioic | Glutaric | 96 | Beet, wood |
| (CH2)4 | Hexanedioic | Adipic | 153 | Not natural (nylon) |
| CH=CH (cis) | cis-Butenedioic | Maleic | 141 | Not natural |
| CH=CH (trans) | trans-Butenedioic | Fumaric | 299 | Metabolic intermediate |
| C≡C | Butynedioic | Acetylenedicarboxylic | 185 | Not natural |