Chapter 15

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

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

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

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

5. Figure 15.2 (continued)

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

7. Some five-carbon skeletons single bonds double bonds ring structures Figure 15.3

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

9. 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. SOLUTION: (a) six carbons, no rings SAMPLE PROBLEM 15.1 Drawing hydrocarbons (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

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

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

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

14. Depicting cycloalkanes cyclobutane cyclopropane Figure 15.6

15. Depicting cycloalkanes cyclohexane cyclopentane Figure 15.6

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

18. An analogy for optical isomers Figure 15.8

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

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

21. The binding site of an enzyme Figure 15.11

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

24. 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. SAMPLE PROBLEM 15.2 Naming alkanes, alkenes and alkynes

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

26. SAMPLE PROBLEM 15.2 (continued)

27. or Representations of benzene Figure 15.12

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. A color test for C=C bonds Figure 15.13

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

32. SAMPLE PROBLEM 15.3 (continued) SOLUTION: 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. Some molecules with the alcohol functional group Figure 15.14

36. the amine functional group primary (1o) amine secondary( 2o) amine tertiary (3o) amine General structures of amines Figure 15.15

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

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

39. 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. SAMPLE PROBLEM 15.4 Predicting the reactions of alcohols, alkyl halides, and amines

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

41. 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-butanone (methyl ethyl ketone) important solvent 2-propanone (acetone) solvent for fat, rubber, plastic, varnish, lacquer; chemical feedstock Some common aldehydes and ketones Figure 15.18

42. The carbonyl group Figure 15.19

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

44. 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) benzoic acid (calorimetric standard; used in preserving food, dyeing fabric, curing tobacco) octadecanoic acid (stearic acid) (found in animal fats; used in making candles and soap) Some molecules with the carboxylic acid functional group Figure 15.20

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

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

47. 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) lysergic acid diethylamide (LSD-25) (a potent hallucinogen) Some molecules with the amide functional group Figure 15.23

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

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

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