Draw structure: Carboxylic acids have higher than expected boiling points due to

Question

Draw structure:

Carboxylic acids have higher than expected boiling points due to dimeric associations involving hydrogen bonding. The structure of 3-methylbutanoic acid (3-methylbutyric acid) is shown below. Draw a second molecule of 3-methylbutanoic acid, and show the hydrogen bonds formed between the molecules in the most stable dimeric structure.

To indicate a hydrogen bond, draw a regular single bond between the atoms, then click on the "graded select" tool (the highlighter) and click on the bond. A selected bond will turn green.

Explanation / Answer

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3-Methylbutanoic acid, or more commonly isovaleric acid, is an organic compound with the formula (CH3)2CHCH2CO2H. It is sometimes classified as a fatty acid. It is a colourless liquid that is sparingly soluble in water, but highly soluble in most common organic solvents. The compound occurs naturally, including in essential oils. Isovaleric acid has a strong pungent cheesy or sweaty smell, but its volatile esters have pleasing scents and are used widely in perfumery. It has been proposed that it is the anticonvulsant agent in valerian. It is a major component of the cause of unpleasant foot odor, as it is produced by skin bacteria metabolizing leucine.

Isovaleric acid is seen as the primary cause of the flavors added to wine caused by Brettanomyces yeasts. Other compounds produced by Brettanomyces yeasts include 4-ethylphenol, 4-vinylphenol, and 4-ethylguaiacol. An excess of isovaleric acid in wine is generally seen as a defect, as it can smell sweaty, leathery, or like a barnyard, but in small amounts it can smell smokey, spicy, or medicinal These phenomena may be prevented by killing any Brettanomycesyeasts, such as by sterile filtration, by the addition of relatively large quantities of sulfur dioxide and sometimes sorbic acid, by mixing in alcoholic spirit to give a fortified wine of sufficient strength to kill all yeast and bacteria, or by pasteurization. Isovaleric acid can also be found in beer, and, excepting some English

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