Alcohols. Characterized by OH group Name: add ol. to name of hydrocarbon. Methanol. Butanol. Sterno. Alcohols burn in air. A mixture of ethanol +

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1 1 2 3 Functional Groups Alcohols Structures of Alcohols haracterized by group Name: add ol to name of hydrocarbon 3 5 : how many structural isomers? See D-RM Screens 11.5 & 11.6 Methanol Butanol 1-propanol 2-propanol Naming: Add -ol- to name of 3- hydrocarbon. Indicate position of with number. Alcohol Properties Alcohols are a derivative of water Many alcohols dissolve in water Sterno Alcohols burn in air A mixture of ethanol + 5 GLYLS Alcohols with Two Groups 6 calcium acetate = STERN Ethylene glycol Propylene glycol Methanol dissolves in water. Butanol is NT soluble in water. 1

2 Substitution Alcohol Reactions Screen 11.6 Elimination the reverse of addition 7 Sugars: Related to Alcohols Sugars are carbohydrates, compounds with the formula x ( 2 ) y α-d-glucose 1 2 What is the difference between and D-glucose? pen chain form β-d-glucose Sucrose and Ribose 2 α-d-glucose Ribose, a pentose in the DNA backbone Fructose 2 9 Amines Alcohols are derivatives of 2 (R ) and amines are derivatives of N Amines Amines generally have terrible odors! 11 Amines Amines, like N 3, are bases N 2 (aq) + 2 S (aq) N 3 + (aq) + S 2- (aq) Methylamine Dimethylamine Trimethylamine adaverine Pyridine Aniline Anilinium ion 2

3 + Amines Nicotine Many natural products and drugs (such as nicotine and cocaine) are bases. 13 Aldehyde ompounds with arbonyl Group arboxylic acid Ketone 1 Structures of Aldehydes innamaldehyde 15 dors from aldehydes and ketones arboxylic Acids Acetic acid Benzoic acid 16 arboxylic Acids 17 Acids + Alcohols 18 Alcohols --> ESTERS Acids are found in many natural substances: bread, fruits, milk, wine arboxylic acid group with acidic + All are WEAK acids Formic acid, 2, gives the sting to ants. 3 Aspirin, acetylsalicylic acid Esters have generally pleasant odors 3

4 19 Acids + Alcohols --> ESTERS Acids + Alcohols --> ESTERS Acetic acid 3-methylbutanol Glycerol Alcohol with 3 Groups 21 Acetic acid Ethanol Ethyl acetate 3 R + + R' R R' methylbutylacetate arboxylic acid Alcohol Ester ne of the important reactions in nature! ombine this with long chain acids >??? Fatty acids ---> fats and oils 2 2 Fats and ils R R R What is the functional group in a fat or oil? R = organic group with N = bonds 12 = Lauric acid 16 = Palmitic acid 18 = Stearic acid R = organic group with = bonds 18 = oleic acid R R R Fats and ils Fats with = bonds are usually LIQUDS leic acid: a monounsaturated fatty acid 23 = bond 2 R R 2 R Fats and ils Fats with saturated acids (no = bonds) are SLIDS. Saturated fats are more common in animals. 2

5 Fats and Polar Bears 25 Bears gorge on blubber in the winter. During the summer bears rely on stored fat for energy. Burn kg of fat per day. Water for metabolism comes from fat burning. Trans Fatty Acids leic acid is a mono unsaturated cis- fatty acid Trans fatty acids have deleterious health effects. Trans fatty acids raise plasma LDL cholesterol and lower DL levels. 26 = bond Fats and ils: Saponification Glyceryl stearate, a fat + Na 2 2 R R R + 3 Na R = ( 2 ) Glycerol + 3 R - Na + 27 Sodium stearate, a soap 28 Acids + Amines --> AMIDES 29 Acids + Amines --> AMIDES Alpha-Amino Acids 30 N-methylacetamide Amide link N Acetoaminophen Tylenol, Datril,, Momentum,... Alanine 3 hiral -carbon N N R Amine Acid 5

6 Peptides and Proteins 3 N 3 Alanine N Serine 2 3 N peptide bond N 3 Adding more peptide links ---> PRTEIN 31 Polymers Giant molecules made by joining many small molecules called monomers Average production is 150 kg per person annually in the U.S. 32 Polymer lassifications Thermoplastics (polyethylene) soften and flow when heated Thermosetting plastics soft initially but set to solid when heated. annot be resoftened. ther classification: plastics, fibers, elastomers,, coatings, adhesives 33 Polymer Preparation 3 Polyethylene: Addition Polymer 35 Mechanism of Addition Polymerization 36 Addition polymers directly adding monomer units together ondensation polymers combining monomer units and splitting out a small water (water) n 2 2 Ethylene n Polyethylene A polymer with a molar mass of 1e6 has about 360,000 units. 6

7 Types of Polyethylene 37 Types of Polyethylene 38 Polystyrene 39 Linear, high density PE (DPE) Polymers based on Substituted Ethylenes, 2 =X n 3 n n Branched, low density PE, LDPE ross-linked PE, LPE polyvinyl alcohol polyvinyl acetate polystyrene Table 11.12: others are PV, acrylonitrile, polypropylene, polymethyl methacrylate Polystyrene is nonpolar material and dissolves in organic solvents. PS foam is mostly air, and when it dissolves it collapses to a much smaller volume Slime! ondensation Polymers Polyesters, PET Slime is polyvinylalcohol cross-linked with boric acid n terephthalic acid + n 2 2 ethylene glycol 2 2 Polyethylene terephthalate (PET), a polyester n + 2 Jackets made from recycled PET soda bottles Soda bottles, mylar film. 7

8 Polyesters: Mechanism 3 Polyamides: Nylon Polyamides: Nylon 5 Each monomer has 6 atoms in its chain. A A polyamide link forms on elmination of l Result = nylon 66 Proteins are polyamides Polymer Recycling Symbols 6 LDPE = Low density PE = g/cm 3 DPE = igh density PE = PP = Polypropylene = 0.90 V = PV (Vinyl chloride) =