1. 15-1 Chapter 15 Organic Compounds and the Atomic Properties of Carbon

2. 15-2 Organic Compounds and the Atomic Properties of Carbon 15.1 The special nature of carbon and the characteristics of organic molecules 15.2 The structures and classes of hydrocarbons 15.3 Some important classes of organic reactions 15.4 Properties and reactivities of common functional groups 15.5 The monomer-polymer theme I: Synthetic macromolecules 15.6 The monomer-polymer theme II: Biological macromolecules

3. 15-3 Figure 15.1 The position of carbon in the periodic table

4. 15-4 Figure 15.2 The chemical diversity of organic compounds 4 carbons linked with single bonds, 1 oxygen and needed hydrogens.

5. 15-5 Figure 15.2(continued)

6. 15-6 HYDROCARBONS Carbon skeletons and hydrogen skins When determining the number of different skeletons, remember that: p Each carbon forms a maximum of four single bonds, OR two single and one double bond, OR one single and triple bond. p The arrangement of carbon atoms determines the skeleton, so a straight chain and a bent chain represent the same skeleton. p Groups joined by single bonds can rotate, so a branch pointing down is the same as one pointing up.

7. 15-7 Some five-carbon skeletons Figure 15.3 single bondsdouble bondsring structures

8. 15-8 Adding a H-atom skin to a carbon skeleton Figure 15.4

9. 15-9 SAMPLE PROBLEM 15.1Drawing hydrocarbons PROBLEM:Draw structures that have different atom arrangements for hydrocarbons with: PLAN:Start with the longest chain and draw shorter chains until you are repeating structures. (a) six C atoms, no multiple bonds, and no rings (b) four C atoms, one double bond, and no rings (c) four C atoms, no multiple bonds, and one ring SOLUTION:(a) six carbons, no rings

10. 15-10 SAMPLE PROBLEM 15.1(continued) (a) continued: (b) four carbons, one double bond(c) four carbons, one ring

11. 15-11 Table 15.1 Numerical Roots for Carbon Chains and Branches number of carbon atoms roots 1 2 3 4 5 6 8 7 9 10 meth- eth- prop- but- hex- pent- hept- oct- non- dec-

12. 15-12

13. 15-13 Figure 15.5 Ways to depict formulas and models of an alkane

14. 15-14 Figure 15.6 Depicting cycloalkanes cyclopropane cyclobutane

15. 15-15 Figure 15.6 Depicting cycloalkanes cyclopentane cyclohexane

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17. 15-17 Figure 15.7 Boiling points of the first 10 unbranched alkanes

18. 15-18 Figure 15.8 An analogy for optical isomers

19. 15-19 Figure 15.9 Two chiral molecules optical isomers of 3-methylhexane optical isomers of alanine

20. 15-20 Figure 15.10 The rotation of plane-polarized light by an optically active substance

21. 15-21 Figure 15.11 The binding site of an enzyme

22. 15-22

23. 15-23 Figure B15.1 The initial chemical event in vision

24. 15-24 SAMPLE PROBLEM 15.2Naming alkanes, alkenes and alkynes PROBLEM:Give the systematic name for each of the following, indicate the chiral center in part (d), and draw two geometric isomers for part (c). PLAN:For (a)-(c), find the longest, continuous chain and give it the base name (root + suffix). Then number the chain so that the branches occur on the lowest numbered carbons and name the branches with the (root + yl). For (d) and (e) the main chain must contain the double bond and the chain must be numbered such that the double bond occurs on the lowest numbered carbon.

25. 15-25 SAMPLE PROBLEM 15.2 SOLUTION: (continued) (can be numbered in either direction) chiral center

26. 15-26 SAMPLE PROBLEM 15.2(continued)

27. 15-27 Figure 15.12 Representations of benzene or

28. 15-28 Types of organic reactions An addition reaction occurs when an unsaturated reactant becomes a saturated product: Elimination reactions are the opposite of addition; they occur when a more saturated reactant becomes a less saturated product: A substitution reaction occurs when an atom (or group) from an added reagent substitutes for one in the organic reactant:

29. 15-29 Figure 15.13 A color test for C=C bonds

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31. 15-31 SAMPLE PROBLEM 15.3Recognizing the type of organic reaction PROBLEM:State whether each reaction is an addition, elimination, or substitution: PLAN:Look for changes in the number of atoms attached to carbon. p More atoms bonded to carbon is an addition. p Fewer atoms bonded to carbon is an elimination. p Same number of atoms bonded to carbon is a substitution.

32. 15-32 SAMPLE PROBLEM 15.3 SOLUTION: (continued) Elimination: there are fewer bonds to last two carbons. Addition: there are more bonds to the two carbons in the second structure. Substitution: the C-Br bond becomes a C-O bond and the number of bonds to carbon remains the same.

33. 15-33 Figure 15.14 Some molecules with the alcohol functional group

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36. 15-36 Figure 15.15 General structures of amines primary (1 o ) aminesecondary( 2 o ) aminetertiary (3 o ) amine the amine functional group

37. 15-37 Figure 15.16 Some biomolecules with the amine functional group lysine (1 o amine) (amino acid found in proteins) adenine (1 o amine) (component of nucleic acids) epinephrine (adrenaline; 2 o amine) (neurotransmitter in brain; hormone released during stress) cocaine (3 o amine) (brain stimulant; widely abused drug)

38. 15-38 Figure 15.17 Structure of a cationic detergent benzylcetyldimethyl- ammonium chloride

39. 15-39 SAMPLE PROBLEM 15.4Predicting the reactions of alcohols, alkyl halides, and amines PROBLEM:Determine the reaction type and predict the product(s) in the following: PLAN:Check for functional groups and reagents, then for inorganics added. In (a) the -OH will substitute in the alkyl halide; in (b) the amine and alkyl halide will undergo a substitution of amine for halogen; in (c) the inorganics form a strong oxidizing agent resulting in an elimination.

40. 15-40 SAMPLE PROBLEM 15.4(continued) SOLUTION: (a) substitution - the products are: (b) substitution - the products are: (c) elimination - the product is:

41. 15-41 Figure 15.18 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 perfume, flavors, plastics, other chemicals benzaldehyde artificial almond flavoring 2-propanone (acetone) solvent for fat, rubber, plastic, varnish, lacquer; chemical feedstock 2-butanone (methyl ethyl ketone) important solvent

42. 15-42 Figure 15.19 The carbonyl group

43. 15-43 SAMPLE PROBLEM 15.5 SOLUTION: Predicting the steps in a reaction sequence PROBLEM:Fill in the blanks in the following reaction sequence: PLAN:Look at the functional groups and reagents to determine the type of reaction.

44. 15-44 Figure 15.20 Some molecules with the carboxylic acid functional group methanoic acid (formic acid) (an irritating component of ant and bee stings) 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 soap) benzoic acid (calorimetric standard; used in preserving food, dyeing fabric, curing tobacco)

45. 15-45 Figure 15.21 Some lipid molecules with the ester functional group cetyl palmitate (the most common lipid in whale blubber) lecithin (phospholipid found in all cell membranes) tristearin (typical dietary fat used as an energy store in animals)

46. 15-46 Figure 15.22 Which reactant contributes which group to the ester?

47. 15-47 lysergic acid diethylamide (LSD-25) (a potent hallucinogen) Figure 15.23 Some molecules with the amide functional group N,N-dimethylmethanamide (dimethylformamide) (major organic solvent; used in production of synthetic fibers) acetaminophen (active ingredient in nonaspirin pain relievers; used to make dyes and photographic chemicals)

48. 15-48 SAMPLE PROBLEM 15.6 SOLUTION: Predicting the reactions of the carboxylic acid family PROBLEM:Predict the product(s) of the following reactions: PLAN:(a) An acid and an alcohol undergo a condensation reaction to form an ester. (b) An amide, in the presence of base and water, is hydrolyzed.

49. 15-49 Figure 15.24 The formation of carboxylic, phosphoric, and sulfuric acid anhydrides

50. 15-50 Figure 15.25 An ester and an amide of other non-metals glucose-6-phosphatesulfanilamide

51. 15-51 SAMPLE PROBLEM 15.7 PROBLEM: SOLUTION: Recognizing functional groups Circle and name the functional groups in the following molecules: PLAN:Use Table 15.5 to identify the functional groups. carboxylic acid ester alcohol 2 o amine ketone alkene haloalkane

52. 15-52 Figure 15.26 A summary of the interconversions among the major organic functional groups

53. 15-53 Figure 15.27 Steps in the free-radical polymerization of ethylene

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56. 15-56 Figure 15.28 The formation of nylon-66

57. 15-57 Figure 15.29 The structure of glucose in aqueous solution and the formation of a disaccharide

58. 15-58 Figure 15.30 The common amino acids

59. 15-59 Figure 15.31 A portion of a polypeptide chain

60. 15-60 Figure 15.32 Forces that maintain protein structure

61. 15-61 Figure 15.33 collagen silk fibroin Shapes of fibrous proteins

62. 15-62 Figure 15.34 mononucleotide of ribonucleic acid (RNA) mononucleotide of deoxyribonucleic acid (DNA) portion of DNA polynucleotide chain Mononucleotide monomers and their linkage

63. 15-63 Figure 15.35 The double helix of DNA 1.08 nm

64. 15-64 Figure 15.36 Key stages in protein synthesis

65. 15-65 Figure 15.37 Key stages of DNA replication