Carboxylic Acid
HONEY JANE ESTARIJA bs-biology MW 1:00 - 2:30 & 3:00 – 6:00
A carboxylic acid is an organic acid characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group. A carboxyl group (or carboxy) is a functional group consisting of a carbonyl (RR'C=O) and a hydroxyl (R-O-H), which has the formula -C(=O)OH, usually written as -COOH or -CO2H.
Carboxylic acids are Brønsted-Lowry acids because they are proton (H+) donors. They are the most common type of organic acid. Among the simplest examples are formic acid H-COOH, which occurs in ants, and acetic acid CH3-COOH, which gives vinegar its sour taste. Acids with two or more carboxyl groups are calleddicarboxylic, tricarboxylic, etc. The simplest dicarboxylic example is oxalic acid (COOH)2, which is just two connected carboxyls. Mellitic acid is an example of a hexacarboxylic acid. Other important natural examples are citric acid (in lemons) and tartaric acid (in tamarinds).
Salts and esters of carboxylic acids are called carboxylates. When a carboxyl group is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate ions are resonance stabilized and this increased stability makes carboxylic acids more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylated forms of the Lewis acid carbon dioxide; under some circumstances they can be decarboxylated to yield carbon dioxide.
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Physical properties
Solubility
Carboxylic acids are polar. Because they are both hydrogen-bond acceptors (the carbonyl) and hydrogen-bond donors (the hydroxyl), they also participate in hydrogen bonding. Together the hydroxyl and carbonyl group forms the functional group carboxyl. Carboxylic acids usually exist as dimeric pairs in nonpolar media due to their tendency to “self-associate.” Smaller carboxylic acids (1 to 5 carbons) are soluble in water, whereas
A carboxylic acid is an organic acid characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group. A carboxyl group (or carboxy) is a functional group consisting of a carbonyl (RR'C=O) and a hydroxyl (R-O-H), which has the formula -C(=O)OH, usually written as -COOH or -CO2H.
Carboxylic acids are Brønsted-Lowry acids because they are proton (H+) donors. They are the most common type of organic acid. Among the simplest examples are formic acid H-COOH, which occurs in ants, and acetic acid CH3-COOH, which gives vinegar its sour taste. Acids with two or more carboxyl groups are calleddicarboxylic, tricarboxylic, etc. The simplest dicarboxylic example is oxalic acid (COOH)2, which is just two connected carboxyls. Mellitic acid is an example of a hexacarboxylic acid. Other important natural examples are citric acid (in lemons) and tartaric acid (in tamarinds).
Salts and esters of carboxylic acids are called carboxylates. When a carboxyl group is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate ions are resonance stabilized and this increased stability makes carboxylic acids more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylated forms of the Lewis acid carbon dioxide; under some circumstances they can be decarboxylated to yield carbon dioxide.
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Physical properties
Solubility
Carboxylic acids are polar. Because they are both hydrogen-bond acceptors (the carbonyl) and hydrogen-bond donors (the hydroxyl), they also participate in hydrogen bonding. Together the hydroxyl and carbonyl group forms the functional group carboxyl. Carboxylic acids usually exist as dimeric pairs in nonpolar media due to their tendency to “self-associate.” Smaller carboxylic acids (1 to 5 carbons) are soluble in water, whereas