Organic Functional Groups

Functional Groups See CD-ROM Screens 11.5 & 11.6 Alcohols Ethers Aldehydes Ketones Acids Amines

Alcohols are a derivative of water Many alcohols dissolve in water Methanol dissolves in water. Butanol is NOT soluble in water.

methyl alcohol (methanol)

ethyl alcohol (ethanol)

n-propyl alcohol (1-propanol)

2-propyl alcohol (isopropanol)

an ALCOHOL R – OH Name: add – ol to name of hydrocarbon Indicate position of -OH with number

TYPES OF ALCOHOLS

GLYCOLS Alcohols with Two OH Groups Propylene glycol Ethylene glycol

Sugars: Related to Alcohols Sugars are carbohydrates, cmpds with the formula C x (H 2 O) y.

Ethers are another derivative of water Many ethers dissolve in water diethyl ether

ethylmethyl ether

an ETHER R - O - R’

Compounds with Carbonyl Group AldehydeAldehyde Carboxylic acid KetoneKetone

methanal FORMALDEHYDE

propanal

H R

an ALDEHYDE Name: add – al to name of hydrocarbon

Cinnamaldehyde Odors from aldehydes and ketones

dimethylketone propanone ACETONE

2-pentanone

3-pentanone

R’R

a KETONE Name: add – one to name of hydrocarbon Indicate position of =O with number

Carboxylic Acids Benzoic acid Carboxylic acid group with acidic H + All are WEAK acids Acetic acid Acids are found in many natural substances: bread, fruits, milk, wine

methanoic acid FORMIC ACID HCOOH, gives the sting to ants.

ethanoic acid ACETIC ACID

butanoic acid BUTYRIC ACID

a CARBOXYLIC ACID Name: add – oic to name of hydrocarbon + acid

While alcohols are derivatives of H 2 O (R–OH), amines are derivatives of NH 3. Methylamine Dimethylamine Trimethylamine

Amines generally have terrible odors! Cadaverine Pyridine

Amines, like NH 3, are bases 2 C 6 H 5 NH 2 (aq) + H 2 SO 4 (aq)  2 C 6 H 5 NH 3 + (aq) + SO 4 2- (aq) aniline anilinium ion

Many natural products and drugs (such as nicotine and cocaine) are bases. Nicotine H+H+

an AMINO ACID

Glycerol Alcohol with 3 OH Groups Combine this with long chain acids  ??? Fatty acids  fats and oils Combine this with long chain acids  ??? Fatty acids  fats and oils

Fats and Oils R = organic group with NO C=C bonds C 12 = Lauric acid C 16 = Palmitic acid C 18 = Stearic acid R = organic group with NO C=C bonds C 12 = Lauric acid C 16 = Palmitic acid C 18 = Stearic acid R = organic group with C=C bonds C 18 = oleic acid R = organic group with C=C bonds C 18 = oleic acid What is the functional group in a fat or oil?

Fats and Oils Fats with C=C bonds are usually LIQUDS Oleic acid: a monounsaturated fatty acid C=C bond

Fats and Oils Fats with saturated acids (no C=C bonds) are SOLIDS. Fats with saturated acids (no C=C bonds) are SOLIDS. Saturated fats are more common in animals.

Fats and Polar Bears Bears gorge on blubber in the winter.Bears gorge on blubber in the winter. During the summer bears rely on stored fat for energy.During the summer bears rely on stored fat for energy. Burn kg of fat per day.Burn kg of fat per day. Water for metabolism comes from fat burning.Water for metabolism comes from fat burning. Bears gorge on blubber in the winter.Bears gorge on blubber in the winter. During the summer bears rely on stored fat for energy.During the summer bears rely on stored fat for energy. Burn kg of fat per day.Burn kg of fat per day. Water for metabolism comes from fat burning.Water for metabolism comes from fat burning.

Trans Fatty Acids Oleic acid is a mono–unsaturated cis-fatty acidOleic acid is a mono–unsaturated cis-fatty acid Trans fatty acids have deleterious health effects.Trans fatty acids have deleterious health effects. Trans fatty acids raise plasma LDL cholesterol and lower HDL levels.Trans fatty acids raise plasma LDL cholesterol and lower HDL levels. CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 CO 2 H

Trans Fatty Acids Food Percentages of Trans- Fatty Acids Butter3.6 Soft Margarine 5.2 Hard Margarine 12.4 Vegetable Oils, Including Safflower, Sunflower, and Soy 0 Beefburger, Fried or Grilled 0.8 Chocolate Cake with Icing 7.1