Ch11_Organic_2 - 1 2 3 Functional Groups Alcohols •...

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Unformatted text preview: 1 2 3 Functional Groups Alcohols • Characterized by –OH group • Name: add –ol to name of hydrocarbon –ol H Structures of Alcohols C3H5OH: how many structural isomers? H C H H C H H C H OH H H C H OH H C H C H H Methanol Butanol See CD-ROM Screens 11.5 & 11.6 1-propanol 2-propanol Naming: Add -ol to name of 3-C hydrocarbon. Indicate -ol position of OH with number. 4 5 Alcohol Properties • Alcohols are a derivative of water • Many alcohols dissolve in water “Sterno” Sterno” • Alcohols burn in air • A mixture of ethanol + calcium acetate = STERNO GLYCOLS Alcohols with Two OH Groups 6 Ethylene glycol Propylene glycol Methanol dissolves Methanol dissolves in water. in water. Butanol is NOT soluble Butanol is NOT soluble in water. in water. 1 7 8 Alcohol Reactions Screen 11.6 Sugars: Related to Alcohols • Sugars are carbohydrates, compounds with the formula Cx(H2O)y. CHO H OH 4 1 2 3 4 5 4 Sucrose and Ribose H OH HO HO H HO H OH O HO Fructose 9 HO H CH2OH H O H H O OH OH H H H H 5 OH H OH OH CH2OH H OH HO HO 5 3 HO HO HO 2 1 3 HO H H H HO 1 2 α-D-Glucose OH H H OH OH OH H H OH H Substitution Elimination—the reverse of addition addition α-D-glucose β-D-glucose Ribose, a pentose in the DNA backbone Open chain form H H CH2 OH What is the difference between What is the difference between and D-glucose? and D-glucose? Amines Alcohols are derivatives of H 2O (R–OH) and amines are derivatives of NH 3. amines are 10 Amines Amines generally have terrible odors! 11 Amines Amines, like NH 3, are bases 2 C6H5NH2 (aq) + H2SO4(aq) 12 2 C6H5NH3 +(aq) + SO42-(aq) Methylamine Dimethylamine Trimethylamine Cadaverine Pyridine Aniline Anilinium ion 2 Amines Many natural products and drugs (such as nicotine and cocaine) are bases. 13 O C Compounds with Carbonyl Group 14 15 Structures of Aldehydes H+ Nicotine Cinnamaldehyde Aldehyde Aldehyde Carboxylic acid Carboxylic acid Ketone Ketone Odors from aldehydes and ketones Carboxylic Acids Acetic acid Benzoic acid 16 Carboxylic Acids 17 Acids + Alcohols --> ESTERS 18 H Acids are found in many natural substances: bread, fruits, milk, wine O C O O C O CH3 Carboxylic acid group with acidic H+ All are WEAK acids Formic acid, HCO2H, gives 2 the sting to ants. Aspirin, acetylsalicylic acid Esters have generally pleasant odors 3 19 20 Acids + Alcohols --> ESTERS O O Acids + Alcohols --> ESTERS Acetic acid 3-methylbutanol Glycerol Alcohol with 3 OH Groups 21 CH3COH + CH3CH2OH Acetic acid Ethanol H+ CH3COCH2CH3 + H2O Ethyl acetate O H3C C O CH3 CH2 CH2CHCH3 O O RC—O—H + R'—O—H Alcohol H+ 3-methylbutylacetate RC—O—R' + H2O Ester Carboxylic acid One of the important reactions in nature! Combine this with long chain acids ------> ??? Fatty acids ---> fats and oils 22 Fats and Oils H2 C HC H2 C O O CR O O CR O O CR R = organic group with NO C=C bonds NO C=C C12 = Lauric acid Lauric C16 = Palmitic acid Palmitic C18 = Stearic acid Stearic R = organic group with C=C bonds C18 = oleic acid oleic H2 C HC H2 C O O CR O O CR O O CR 23 Fats and Oils H2 C HC H2 C O O CR O O CR O O CR 24 Fats and Oils Fats with C=C bonds are usually LIQUDS Fats with saturated acids (no C=C bonds) are SOLIDS. Oleic acid: a monounsaturated fatty acid What is the functional group in a in fat or oil? Saturated fats are more common in animals. C=C bond 4 25 26 Fats and Polar Bears •Bears gorge on blubber in the winter. •During the summer bears rely on stored fat for energy. •Burn 1-1.5 kg of fat per day. •Water for metabolism comes from fat burning. Trans Fatty Acids •Oleic acid is a mono–unsaturated ciscisfatty acid •Trans fatty acids have deleterious health effects. •Trans fatty acids raise plasma LDL cholesterol and lower HDL levels. Fats and Oils: Saponification Glyceryl stearate, a fat + NaOH O O CR O + 3 NaOH O CR CH O CH2 O CR R = —(CH2 )16CH3 CH2 O—H CH O—H CH2 O—H CH2 27 O + 3 RC—O- Na+ Sodium stearate, a soap C=C bond Glycerol 28 29 30 Acids + Amines --> AMIDES Acids + Amines --> AMIDES H H H H C H H O C N C C C H C C C H H O Alpha-Amino Acids H H2 N C O C OH R Amine Chiral -carbon Acid Amide link Alanine H C N-methylacetamide N-methylacetamide Acetoaminophen Tylenol, Datril, Momentum, ... Datril, H3 C NH3 CO2 5 31 Peptides and Proteins O H 3N O– H CH3 Alanine + Polymers • Giant molecules made by joining many small molecules called monomers monomers • Average production is 150 kg per person annually in the U.S. 32 33 Polymer Classifications • Thermoplastics (polyethylene) soften and flow when heated • Thermosetting plastics — soft initially but set to solid when heated. Cannot be resoftened. resoftened. • Other classification: plastics, fibers, plastics, elastomers, coatings, adhesives elastomers, HOCH2 H 3N H O– O Serine peptide bond H HOCH2 H 3N O H N H O O– CH3 Adding more peptide links ---> PROTEIN 34 Polymer Preparation • Addition polymers — directly polymers adding monomer units together • Condensation polymers — polymers combining monomer units and splitting out a small water (water) Polyethylene: Addition Polymer H n H2 C CH2 C H H C Hn 35 Mechanism of Addition Polymerization 36 Ethylene Polyethylene A polymer with a molar mass of 1e6 has about 360,000 units. 6 37 38 Types of Polyethylene Linear, high density PE (HDPE) Types of Polyethylene Polymers based on Substituted Ethylenes, CH2=CHX Polystyrene 39 CH2CH OH n CH2CH OCCH3 n O polyvinyl acetate CH2CH n polyvinyl alcohol polystyrene Branched, low density PE, LDPE Table 11.12: others are PVC, acrylonitrile, acrylonitrile, polypropylene, polymethyl methacrylate Cross-linked PE, CLPE • 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. 40 41 42 Slime! Slime is polyvinylalcohol cross-linked with boric acid Condensation Polymers O n HOC Polyesters, PET O COH + n HOCH2CH2OH ethylene glycol terephthalic acid O C O COCH2CH2O n + H2 O Jackets made from recycled PET soda bottles Soda bottles, mylar film. Polyethylene terephthalate (PET), a polyester 7 43 44 45 Polyesters: Mechanism Polyamides: Nylon Polyamides: Nylon •Each monomer has 6 C atoms in its chain. •A polyamide link forms on elmination of HCl •Result = nylon 66 •Proteins are polyamides 46 Polymer Recycling Symbols LDPE = HDPE = PP = V= Low density PE = 0.910-0.925 g/cm 3 High density PE = 0.941-0.965 Polypropylene = 0.90 PVC (Vinyl chloride) = 1.30-1.58 8 ...
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This note was uploaded on 01/11/2011 for the course ENGINEERIN MAE 107 taught by Professor Pozikrizdis during the Fall '08 term at San Diego.

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