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  • 1. ORGANIC CHEMISTRY III • • • • • • 15-1 CARBOXYLIC ACIDS DERIVATIVES OF ACIDS ALDEHYDES/KETONES AMINES ETHERS Chapter 15.4 Silberberg
  • 2. Chapter 15 Organic Compounds and the Atomic Properties of Carbon 15-2
  • 3. Organic Compounds and the Atomic Properties of Carbon 15.3 Some Important Classes of Organic Reactions 15.4 Properties and Reactivities of Common Functional Groups 15-3
  • 4. Goals & Objectives • See the following Learning Objectives on page 676. • Master these Skills: • 15.6, 8-10. 15-4
  • 5. Table 15.5 15-5 Important Functional Groups in Organic Compounds
  • 6. Table 15.5 15-6 Important Functional Groups in Organic Compounds
  • 7. Amines The amine functional group contains a N atom. The systematic name for an amine is formed by dropping the final –e of the alkane and adding the suffix –amine. Common names that use the name of the alkyl group followed by the suffix –amine are also widely used. 15-7
  • 8. Figure 15.17 General structures of amines. Amines are classified according to the number of R groups directly attached to the N atom. 15-8
  • 9. Figure 15.18 Some biomolecules with the amine functional group. Lysine (1 amine) amino acid found in proteins Epinephrine (adrenaline; 2 amine) neurotransmitter in brain; hormone released during stress 15-9 Adenine (1 amine) component of nucleic acids Cocaine (3 amine) brain stimulant; widely abused drug
  • 10. Properties and Reactions of Amines Primary and secondary amines can form H bonds; therefore they have higher melting and boiling points than hydrocarbons or alkyl halides of similar mass. Tertiary amines cannot form H bonds between their molecules because they lack a polar N–H bond. Amines of low molar mass are fishy smelling, water soluble, and weakly basic. Amines undergo a variety of reactions, including substitution reactions. 15-10
  • 11. Sample Problem 15.4 Predicting the Reactions of Alcohols, Alkyl Halides, and Amines PROBLEM: Determine the reaction type and predict the product(s) for each reaction: PLAN: 15-11 We first determine the functional group(s) of the reactant(s) and then examine any inorganic reagent(s) to decide on the reaction type. Keep in mind that, in general, these functional groups undergo substitution or elimination.
  • 12. Sample Problem 15.4 SOLUTION: (a) In this reaction the OH of the NaOH reaction substitutes for the I in the organic reagent: (b) This is a substitution reaction: (c) This is an elimination reaction since acidic Cr2O72- is a strong oxidizing agent: 15-12
  • 13. Amines • Classification • NH3 RNH2 • 1O 15-13 R2NH 2O R 3N 3O
  • 14. Amines • • • • • • 15-14 Nomenclature CH3NH2 (CH3)2NH (CH3)3N CH3NHCH2CH3 (CH3)2NCH2CH3
  • 15. 15-15
  • 16. Amines • Reactions – organic bases – RNH2 + H2O ---> RNH3+ + OH– CH3NH2 + HCl ---> CH3NH3+ + Cl– CH3NH2. HCl – methylamine hydrochloride 15-16
  • 17. Aldehydes and Ketones Aldehydes and ketones both contain the carbonyl group, C=O. R and R′ indicate hydrocarbon groups. Aldehydes are named by replacing the final –e of the alkane name with the suffix –al. Ketones have the suffix –one and the position of the carbonyl must always be indicated. 15-17
  • 18. Figure 15.20 Some common aldehydes and ketones. Methanal (formaldehyde) Used to make resins in plywood, dishware, countertops; biological preservative Ethanal (acetaldehyde) Narcotic product of ethanol metabolism; used to make perfumes, flavors, plastics, other chemicals 15-18 Benzaldehyde Artificial almond flavoring 2-Propanone (acetone) Solvent for fat, rubber, plastic, varnish, lacquer; chemical feedstock 2-Butanone (methyl ethyl ketone) Important solvent
  • 19. Figure 15.21 The polar carbonyl group. The C=O bond is electron rich and is also highly polar. It readily undergoes addition reactions, and the electron-poor C atom attracts electron-rich groups. 15-19
  • 20. Reactions of Aldehydes and Ketones Reduction to alcohols is an example of an addition reaction: Organometallic compounds, which have a metal atom covalently bonded to C, add to the electron-poor carbonyl C: 15-20
  • 21. Sample Problem 15.5 Predicting the Steps in a Reaction Sequence PROBLEM: Fill in the blanks in the following reaction sequence: PLAN: For each step we examine the functional group of the reactant and the reagent above the yield arrow to decide on the most likely product. SOLUTION: 15-21 The first step involves an alkyl halide reacting with OH-, so this is probably a substitution reaction, which yields an alcohol. In the next step the alcohol is oxidized to a ketone and finally the organometallic reagent adds to the ketone to give an alcohol with one more C in its skeleton:
  • 22. Sample Problem 15.5 15-22
  • 23. Aldehydes • • • • • • 15-23 Nomenclature IUPAC HCHO CH3CHO CH3CH2CHO CH3CH2CH2CHO TRIVIAL
  • 24. 15-24
  • 25. 15-25
  • 26. Aldehydes • Preparation – RCH2OH + [O] ---> RCHO – CH3CH2OH + [O] ---> CH3CHO – Prepare • 3-methylpentanal • 2,4-dimethylhexanal 15-26
  • 27. 15-27
  • 28. 15-28
  • 29. Ketones, RCOR‟ • • • • • 15-29 Nomenclature IUPAC CH3COCH3 CH3COCH2CH3 CH3COCH2CH2CH3 TRIVIAL
  • 30. 15-30
  • 31. 15-31
  • 32. Ketones • Preparation – OH – RCHR‟ + [O] ---> RCOR‟ – OH – CH3CHCH3 + [O] ---> CH3COCH3 • Prepare: – 3-hexanone – 2-methyl-3-pentanone 15-32
  • 33. 15-33
  • 34. 15-34
  • 35. 15-35
  • 36. Carboxylic Acids Carboxylic acids contain the functional group –COOH, or Carboxylic acids are named by replacing the –e of the alkane with the suffix –oic acid. Carboxylic acids are weak acids in water, and react with strong bases: 15-36
  • 37. Figure 15.22 Some molecules with the carboxylic acid functional group. Methanoic acid (formic acid) An irritating component of ant and bee stings Benzoic acid Calorimetric standard; used in preserving food, dyeing fabric, curing tobacco 15-37 Butanoic acid (butyric acid) Odor of rancid butter; suspected component of monkey sex attractant Octadecanoic acid (stearic acid) Found in animal fats; used in making candles and soaps
  • 38. Carboxylic Acids, RCOOH • • • • • • 15-38 Nomenclature IUPAC HCOOH CH3COOH CH3CH2COOH CH3CH2CH2COOH TRIVIAL
  • 39. 15-39
  • 40. 15-40
  • 41. Carboxylic Acids, RCOOH • Preparation – RCH2OH + xs[O] ----> RCOOH – CH3CH2OH + xs[O] ----> CH3COOH • Reaction--as acid – RCOOH + NaOH ----> RCOONa – CH3COOH + NaOH ----> CH3COONa – sodium acetate 15-41
  • 42. Derivatives of Carboxylic Acids • Acid Chlorides, RCOCl – Nomenclature • “oic acid” becomes „yl chloride” • CH3CH2COCl – Preparatio • RCOOH + PCl3 ----> RCOCl 15-42
  • 43. 15-43
  • 44. Esters The ester group is formed by the reaction of an alcohol and a carboxylic acid. Esterification is a dehydration-condensation reaction. Ester groups occur commonly in lipids, which are formed by the esterification of fatty acids. 15-44
  • 45. Figure 15.23 Some lipid molecules with the ester functional group. Cetyl palmitate The most common lipid in whale blubber Lecithin Phospholipid found in all cell membranes 15-45 Tristearin Typical dietary fat used as an energy store in animals
  • 46. Derivatives of Carboxylic Acids • Esters, RCOOR‟ – Preparation and Nomenclature – RCOCl + R‟OH ----> RCOOR‟ + HCl – CH3COCl + CH3CH2OHCH3COOCH2CH3 – ethyl acetate – or ethyl ethanoate 15-46
  • 47. Table 1. Names, Structures, and Fruit and Flower Aromas of Some Common Natural Esters Ester Name Aroma 3-Methylbutyl acetate Bananas n-Butyl acetate n-Octyl acetate Oranges Benzyl acetate Peaches Benzyl butyrate 15-47 Pears Flowers* Ethyl butyrate Pineapples
  • 48. 15-48
  • 49. 15-49
  • 50. Saponification Ester hydrolysis can be carried out using either aqueous acid or aqueous base. When base is used the process is called saponification. This is the process used to make soaps from lipids. 15-50
  • 51. Amides An amide contains the functional group: Amides, like esters, can be hydrolyzed to give a carboxylic acid and an amine. The peptide bond, which links amino acids in a protein, is an amide group. 15-51
  • 52. Figure 15.24 Some molecules with the amide functional group. Acetaminophen Active ingredient in nonaspirin pain relievers; used to make dyes and photographic chemicals N,N-Dimethylmethanamide (dimethylformamide) Major organic solvent; used in production of synthetic fibers 15-52 Lysergic acid diethylamide (LSD-25) A potent hallucinogen
  • 53. Derivatives of Carboxylic Acids • Amides, RCONH2 – Preparation and Nomenclature – RCOCl + NH3 ----> RCONH2 + HCl – CH3COCl + NH3 ----> CH3CONH2 – ethanamide – acetamide 15-53
  • 54. Sample Problem 15.6 Predicting the Reactions of the Carboxylic Acid Family PROBLEM: Predict the product(s) of the following reactions: PLAN: We identify the functional groups in the reactant(s) and see how they change. In (a), a carboxylic acid reacts with an alcohol, so the reaction must be a substitution to form an ester. In (b), an amide reacts with aqueous base, so hydrolysis occurs. 15-54
  • 55. Sample Problem 15.6 SOLUTION: 15-55
  • 56. Ethers, ROR‟ • HOH • water 15-56 ROH alcohol ROR‟ ether
  • 57. Ethers, ROR‟ • • • • • 15-57 Nomenclature Use common names CH3OCH3 CH3OCH2CH3 CH3OCH2CH2CH2CH3
  • 58. 15-58
  • 59. Alexander Williamson • Alexander William Williamson (May 1, 1824 – May 6, 1904), an English chemist, was born at Wandsworth, London. Williamson is remembered for his research on the formation of ether. For his work on etherification, Williamson received a Royal medal from the Royal Society in 1862. 15-59
  • 60. Ethers, ROR‟ • Preparation (Williamson synthesis) • RONa + R‟I ---> ROR‟ + NaI • Outline a synthesis of each of the following: • ethylmethyl ether • ethoxybutane 15-60
  • 61. 15-61
  • 62. 15-62
  • 63. Polymers Addition polymers, also called chain-growth polymers form when monomers undergo an addition reaction with each other. The monomers of most addition polymers contain an alkene group. Condensation polymers are formed when monomers link by a dehydration-condensation type reaction. The monomers of condensation polymers have two functional groups, and each monomer can link to two others. 15-63
  • 64. Figure 15.27 Steps in the free-radical polymerization of ethylene. 15-64
  • 65. Table 15.6 15-65 Some Major Addition Polymers
  • 66. Table 15.6 15-66 Some Major Addition Polymers
  • 67. Figure 15.28 The formation of nylon-66. Nylon-66 is a condensation polymer, made by reacting a diacid with a diamine. The polyamide forms between the two liquid phases. 15-67