Ch11_Organic_2 - 1 2 Functional Groups 3 Alcohols...

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Unformatted text preview: 1 2 Functional Groups 3 Alcohols Structures of Alcohols Structures Alcohols • Characterized by –OH group • Name: add – ol to name of hydrocarbon C3H5OH: how many structural isomers? H Methanol Butanol C H H H OH OH H C C C H H H H H 2-propanol Naming: Add -ol to name of 3-C hydrocarbon. Indicate ol to position of OH with number. 4 • Alcohols are a derivative of water Alcohols are • Many alcohols dissolve in water Many dissolve H C 1-propanol See CD-ROM Screens 11.5 & 11.6 Alcohol Properties H C H H 5 “Sterno” GLYCOLS Alcohols with Two OH Groups 6 • Alcohols burn in air Alcohols burn • A mixture of ethanol + calcium acetate = STERNO Methanol dissolves Methanol dissolves in water. in water. Ethylene glycol Propylene glycol Butanol is NOT soluble Butanol iis NOT soluble s in water. in water. 1 7 Alcohol Reactions 8 Sugars: Related to Alcohols Sugars: Alcohols Screen 11.6 H OH • Sugars are carbohydrates, compounds with the formula Cx(H2O)y. with CHO H OH 4 HO HO 5 3 H H Substitution Methylamine Dimethylamine OH OH HO H H H HO HO HO H 1 OH 2 H H OH 3 OH 4 OH 4 HO HO 5 5 1 H H CH2OH H HO 3 2 OH H What is the difference between What is the difference between HO OH O H OH H HO Fructose β-D-glucose H CH2OH α-D-Glucose Open chain form 10 Amines 2 1 α-D-glucose Elimination—the reverse of addition reverse addition Alcohols are derivatives of H 2O (R–OH) Alcohols are and amines are derivatives of NH 3. and amines H HO 9 Sucrose and Ribose H O OH OH H H H Ribose, a pentose in the DNA backbone OH H O H CH2 OH and D-glucose? and D-glucose? 11 Amines Amines generally have terrible odors! Amines 12 Amines, like NH 3, are bases 2 C6H5NH2 (aq) + H2SO4(aq) 2 C6H5NH3 +(aq) + SO42-(aq) Trimethylamine Cadaverine Pyridine Aniline Anilinium ion 2 13 Amines O C Nicotine H+ Many natural products and drugs (such as nicotine and cocaine) are bases. Carboxylic Acids Acetic acid Aldehyde Aldehyde 16 14 Compounds with Carbonyl Group Carboxylic acid Carboxylic acid 15 Structures of Aldehydes Structures Aldehydes Cinnamaldehyde Ketone Ketone 17 Carboxylic Acids Odors from aldehydes and Odors and ketones 18 Acids + Alcohols --> ESTERS Acids --> Benzoic acid H Acids are found in many natural substances: bread, fruits, milk, wine O Carboxylic acid group with acidic H+ All are WEAK acids All WEAK Formic acid, HCO2H, gives 2 the sting to ants. C O O C CH3 O Aspirin, acetylsalicylic acid Esters have generally pleasant odors 3 19 20 Acids + Alcohols --> ESTERS Acids --> Acids + Alcohols --> ESTERS Acids --> O O CH3COH + CH3CH2OH Acetic acid H+ Ethyl acetate O H3C O O + R'—O—H Carboxylic acid Alcohol 3-methylbutanol Acetic acid H+ C CH3 O CH2 CH2CHCH3 3-methylbutylacetate RC—O—R' + H2O Ester Combine this with long chain acids ------> ??? Fatty acids ---> fats and oils One of the important reactions in nature! Fats and Oils H2 C HC H2 C O O CR O O CR O O CR What is the functional group in a fat or oil? 21 CH3COCH2CH3 + H2O Ethanol RC—O—H Glycerol Alcohol with 3 OH Groups 22 H2 C HC H2 C R = organic group with NO C=C bonds with NO C12 = Lauric acid Lauric acid C16 = Palmitic acid acid C18 = Stearic acid acid R = organic group with C=C bonds C18 = oleic acid O O CR O O CR O O CR Fats and Oils 23 H2 C HC H2 C Fats with C=C bonds are usually LIQUDS O O CR O O CR O O CR Fats and Oils 24 Fats with saturated acids (no C=C bonds) are SOLIDS. Oleic acid: a monounsaturated fatty acid Saturated fats are more common in animals. C=C bond 4 Fats and Polar Bears 25 •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 26 27 Fats and Oils: Saponification Fats Saponification Glyceryl stearate, a fat + NaOH •Oleic acid is a mono–unsaturated cisOleic cis fatty acid •Trans fatty acids have deleterious health effects. •Trans fatty acids raise plasma LDL cholesterol and lower HDL levels. 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 C=C bond 28 Sodium stearate, a soap Glycerol 29 Acids + Amines --> AMIDES O + 3 RC—O- Na+ Acids + Amines --> AMIDES H H H C C O C Alpha-Amino Acids H H C H 30 H2 N O C C OH R C C N C H Amine H H H H Amide link Alanine N-methylacetamide O C Acetoaminophen Tylenol, Datril, Momentum, ... Tylenol, Datril Datril, H3 C C Acid Chiral -carbon NH3 CO2 5 31 Polymers Peptides and Proteins O H 3N O– H CH3 Alanine HOCH2 + H 3N H O– peptide bond HOCH2 H H 3N O N H 33 Polymer Classifications • Thermoplastics (polyethylene) soften and flow when heated • Thermosetting plastics — soft initially but set to solid when heated. Cannot be resoftened . • Giant molecules made by joining many small molecules called monomers small monomers • Average production is 150 kg per person annually in the U.S. O Serine H 32 O • Other classification: plastics, fibers, Other plastics, elastomers , coatings, adhesives O– CH3 Adding more peptide links ---> PROTEIN 34 Polymer Preparation • Addition polymers — directly adding monomer units together • Condensation polymers — combining monomer units and splitting out a small water (water) Polyethylene: Addition Polymer H CH2 Ethylene Mechanism of Addition Polymerization 36 H C C H n H2 C 35 Hn Polyethylene A polymer with a molar mass of 1e6 has about 360,000 units. 6 37 Types of Polyethylene 38 Types of Polyethylene Polystyrene 39 Polymers based on Substituted Ethylenes, CH2=CHX Linear, high density PE (HDPE) CH2CH OH OCCH3 n O polyvinyl alcohol Branched, low density PE, LDPE CH2CH CH2CH n n polyvinyl acetate polystyrene • Polystyrene is nonpolar material and dissolves Polystyrene material in organic solvents. • PS foam is mostly air, and when it dissolves it collapses to a much smaller volume. Table 11.12: others are PVC, acrylonitrile, Table acrylonitrile polypropylene, polymethyl methacrylate polypropylene, polymethyl Cross-linked PE, CLPE 40 Slime! Slime is polyvinylalcohol cross-linked with boric acid 41 Condensation Polymers O 42 Polyesters, PET O COH + n HOCH2CH2OH n HOC terephthalic acid O C ethylene glycol O COCH2CH2O + H2 O n Jackets made from recycled PET soda bottles Soda bottles, mylar Soda mylar film. Polyethylene tere phthalate (PET), a polyester 7 43 Polyesters: Mechanism 44 Polyamides: Nylon 45 Polyamides: Nylon •Each monomer has 6 C atoms in its chain. •A polyamide link forms on elmination of HCl polyamide HCl •Result = nylon 66 •Proteins are polyamides Proteins polyamides 46 Polymer Recycling Symbols LDPE = LDPE HDPE = HDPE PP = PP V= Low density PE = 0.910-0.925 g/cm 3 Low High density PE = 0.941-0.965 High Polypropylene = 0.90 Polypropylene PVC (Vinyl chloride) = 1.30-1.58 PVC 8 ...
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This note was uploaded on 10/19/2011 for the course CHM 2210 taught by Professor Mcquade during the Fall '08 term at FSU.

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