ACTIVITY 2 (Nomenclature of Carboxylic Acids)

Carboxylic Acids Suffix: -oic acid Prefix: carboxy-

Carboxylic acids contain a functional group, commonly written as -CO2H or COOH (note: the acidic hydrogen is bold). The carbon atom of the acid (the carbonyl carbon) will be atom number 1 in the numbering scheme. Since it always occurs at the end(s) of the chain of carbon atoms, the number is omitted. In naming the acid, the final -e of the alkane is replaced by -oic acid (note: two words in the name). The general formula for an acid is CnH2nO2. As with several of the other functional groups discussed to this point, there are a large number of acids with common names which will be underlined.

When the -CO2H group is attached to a ring, the acid is named as a cycloalkane carboxylic acid (note the -e is retained). Di-acids occur as well. In this case, since the acid groups must be at each end of the chain, numbers are not necessary to indicate their location.

Examples naming simple acids: Compound Name methanoic acid or formic acid ethanoic acid or acetic acid propanoic acid

Line Drawing

2-methylpropanoic acid

cyclobutane carboxylic acid

ethanedioic acid * or oxalic acid propanedioic acid * or malonic acid

butanedioic acid * or succinic acid

hexanedioic acid * or adipic acid

* Note: the terminal -e is retained as the dioic begins with a consonant.

Examples naming more complex acids: Compound Name 2-hydroxypropanoic acid or lactic acid Line Drawing

5,5-dimethyl-3-oxohexanoic acid

Acids as Substituents: In more complex molecules with higher priority functional groups, the acid is named as a carboxy- substituent. It is located by numbering the longest chain of carbons (according to the higher priority functional group) and locating the -CO2H group by this numbering scheme.

Nomenclature and examples Carboxylic acids are commonly named as indicated in the table below. Although rarely used, IUPAC-recommended names also exist. For example, butyric acid (C3H7CO2H) is, according to IUPAC guidelines, also known as butanoic acid. The carboxylate anion R-COO is usually named with the suffix -ate, so acetic acid, for example, becomes acetate ion. In IUPAC nomenclature, carboxylic acids have an -oic acid suffix (e.g., octadecanoic acid). In common nomenclature, the suffix is usually -ic acid (e.g.,stearic acid). Straight-chained, saturated carboxylic acids

Carbon atoms Common name

IUPAC name

Chemical formula

Common location or use

Formic acid

Methanoic acid

HCOOH

Insect stings

Acetic acid

Ethanoic acid

CH3COOH

Vinegar

Propionic acid

Propanoic acid

CH3CH2COOH

Preservative for stored grains

Butyric acid

Butanoic acid

CH3(CH2)2COOH

Rancid butter

Valeric acid

Pentanoic acid

CH3(CH2)3COOH

Valerian

Caproic acid

Hexanoic acid

CH3(CH2)4COOH

Goat fat

Enanthic acid

Heptanoic acid

CH3(CH2)5COOH

Caprylic acid

Octanoic acid

CH3(CH2)6COOH

Coconuts and breast milk

Pelargonic acid Nonanoic acid

CH3(CH2)7COOH

Pelargonium

10

Capric acid

Decanoic acid

CH3(CH2)8COOH

11

Undecylic acid

Undecanoic acid

CH3(CH2)9COOH

12

Lauric acid

Dodecanoic acid

CH3(CH2)10COOH

Coconut oil and hand wash soaps.

13

Tridecylic acid

Tridecanoic acid

CH3(CH2)11COOH

14

Myristic acid

Tetradecanoic acid CH3(CH2)12COOH

Nutmeg

15

Pentadecanoic acid CH3(CH2)13COOH

16

Palmitic acid

Hexadecanoic acid CH3(CH2)14COOH

Palm oil

17

margaric acid

Heptadecanoic acid CH3(CH2)15COOH

18

Stearic acid

Octadecanoic acid

CH3(CH2)16COOH

Chocolate, waxes, soaps, and oils

20

Arachidic acid

Icosanoic acid

CH3(CH2)18COOH

Peanut oil

Other carboxylic acids

Compound class

Members

unsaturated monocarboxylic acids

acrylic acid (2-propenoic acid) CH2=CHCOOH, used in polymer synthesis

Fatty acids

medium to long-chain saturated and unsaturated monocarboxylic acids, with even number of carbons examplesdocosahexaenoic acid and eicosapentaenoic acid (nutritional supplements)

Amino acids

the building blocks of proteins

Keto acids

acids of biochemical significance that contain a ketone group e.g. acetoacetic acid and pyruvic acid

Aromatic carboxylic acids

benzoic acid, the sodium salt of benzoic acid is used as a food preservative, salicylic acid a beta hydroxy type found in many skin care products

Dicarboxylic acids

containing two carboxyl groups examples adipic acid the monomer used to produce nylon and aldaric acid a family of sugar acids

Tricarboxylic acids

containing three carboxyl groups example citric acid found in citrus fruits and isocitric acid

Alpha hydroxy acids

containing a hydroxy group example glyceric acid, glycolic acid and lactic acid (2hydroxypropanoic acid) found in sour milk tartaric acid - found in wine

ACTIVITY: Lotion Making Ever wondered which ingredient makes up the largest percentage in lotions? Water! If you look at the ingredients list on product labels, you will notice that water is almost always listed first, meaning it is the most predominant ingredient in the product. And, it is also 'free' and readily available. So what all are you paying for? Skin care lotion is nothing more than an emulsion of oil and water. As an introduction to this wonderful and useful craft, let's make a simple lotion with just olive oil, water, and emulsifying wax. Here's what you need to make approximately a 12 fl oz batch.

Step 1Tools and Ingredients

Tools: - 1-cup glass measuring cup - 2-cup glass measuring cup - saucepan just large enough to fit the 1-cup measurer Ingredients: - 1/4 cup olive oil - 1 1/4 cup water - 1/4 cup emulsifying wax, available at some craft stores or online. Step 2Water Bath

Fill a small saucepan with water and set it on medium low to use as a water bath. Step 3Melt Oil and Wax

Combine the oil and e. wax into the heatproof 1-cup measurer and melt the mixture in the water bath.

Step 4Heat Water

Fill the 2-cup measurer with water and heat it in the microwave on high for 2 minutes or until it boils. Alternatively, boil water on the stove and pour it into the measurer. Step 5Combine

When the oil/wax mixture has melted, pour it into the water. Your lotion should now have the consistency of skim milk. Step 6Cool Slightly and Pour/Package

Let it cool slightly, stir with a spoon or chopstick and pour the lotion into a bottle while it's still warm and pourable. Otherwise, it would be hard to get the lotion into its container and you might have to use a funnel. If you're using a wide mouth jar, then this is not an issue. Step 7Shake Well

Leave the cap off to let it cool completely, but occasionally cap the lotion and give it a quick shake to help blend the mixture. Step 8Ways to Customize As is, this plain, scent-free lotion is great for babies and people with sensitive skin. But this recipe is very forgiving and you can easily vary it. Here are some suggestions: - Substitute 1/4 to 1/2 cup of the water with glycerin to make a hydrating lotion. - Substitute or combine the olive oil with other oils such as almond oil or coconut oil - Add essential oils. Use 1 - 5 drops per fl oz of lotion

ACTIVITY 2 (Nomenclature of Carboxylic Acids) Name the following structures of carboxylic acids:

1. 2. 3.

4. 5.

6. 7.

8. 9.

10.

11. 12.

13.

14.

15.

KEY TO CORRECTION:

1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15.

3-ethylpentanoic acid butanedioic acid propyl pentanoate pentanoic anhydride 3-methylbutanoic acid 2-chlorobutanoic acid ethanoyl chloride benzene-1,2-dicarboxylic acid 2-methylpropanoic acid 2-hydroxybutanoic acid Sodium benzoate potassium ethanoate 2-chlorocyclopentanecarboxylic acid cyclobutanecarboxylic acid 4-amino-6-heptenoic acid