1. Organic chemistry is the study of the properties of the compounds of carbon. Just about everything in this world has carbon, C, in it!

2. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 2 Learning Objectives a.Organic molecules form the basis for life and include many natural products with medicinal properties. b.After the structure of a biologically active compound is determined, organic chemists can often synthesize the compound, as well as new derivatives with more powerful activities.

3. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 3 Learning Objectives (cont) c.Most organic compounds contain a hydrocarbon framework containing chains of carbon atoms and bonded hydrogen atoms ( “ hydrocarbons ” ). d.Hydrocarbons are classified according to types of carbon-carbon bonds. Alkanes contain only single bonds, alkenes contain at least one double bond, alkynes contain at least one triple bond, and aromatics are rings that contain alternating single and double bonds.

4. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 4 Learning Objectives (cont) e.Adding different atoms or groups of atoms (functional groups) to a hydrocarbon results in new classes of compounds with distinctive chemical properties. f.The geometric arrangement of atoms within an organic compound determines its activity. g.Two mirror-image molecules (enantiomers) with the same chemical formula and connections of the atoms can have different biological activities.

5. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 5 General Properties of Organic Compounds a.Review of Carbon 1.Carbon has four electrons in its outer shell and therefore can form four covalent bonds. b.Polarity 1.Organic molecules contain many nonpolar C-H bonds and are therefore generally hydrophobic.

6. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 6 Three ways in which carbon can fulfill its octet

7. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 7 Effect of differences in electronegativity on charge distribution

8. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 8 General Properties of Organic Compounds c.Intermolecular Forces 1.Small hydrocarbons interact through relatively weak London forces and therefore tend to be gases at room temperature.

9. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 9 Melting and Boiling Points of Hydrocarbons

10. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 10 General Properties of Organic Compounds c.Intermolecular Forces 3.Large hydrocarbons and those containing bonded polar atoms are often liquids or solids at room temperature. 4.Organic molecules containing bonded polar atoms are generally more water soluble than those containing only carbon and hydrogen. (Like dissolves like.)

11. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 11 Water Solubility of Alcohols vs. Alkanes OH groups can make a molecule, with less than 8 carbons, water soluble

12. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 12 Natural Products a.Some compounds found in nature (natural products) have interesting properties, such as medicinal activity. b.Once the structure of a natural product is determined, chemists may seek to synthesize the compound in the laboratory. c.Parent compounds, like salicin, serve as the structural basis for new synthetic molecules (derivatives or analogues).

13. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 13 Synthesis of Derivatives The willow tree, source of the active ingredient of aspirin

14. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 14 The Pacific yew tree, source of taxol A molecule with powerful Anticancer activity!

15. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 15 Types of Hydrocarbons a.Alkanes: contain only single carbon-carbon bonds b.Alkenes: contain at least one double carbon- carbon bond c.Alkynes: contain at least one triple carbon- carbon bond d.Aromatics: ringed hydrocarbons with alternating single and double bonds between carbons.

16. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 16 Examples of Straight-Chain Alkanes

17. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 17 Reduction of hydrocarbons vs. oxidation

18. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 18 Reactivity of Alkanes Hydrocarbon + O 2  carbon dioxide + water + heat energy  Ex. CH 4 + 2O 2  CO 2 + 2H 2 O  Heat released is 802 kJ/mol of methane Effect of partially oxidizing a hydrocarbon, let’s look at the combustion reaction of CH 3 OH (methanol), in which 1 H has been replaced by an –OH group. 2CH 3 OH + 3O 2  2CO 2 + 4H 2 O Heat released is 640 kJ/mol of methanol (1.5 moles of O 2 required to with 1 mole of CH 3 OH!) 

19. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 19 These reactions illustrates two important principles. 1 st, the more reduced a molecule, the more energy is released during oxidation on a molar basis. Methane is fully reduced and gives off more energy during combustion than methanol. 2 nd, the number of oxygen molecules required to react with a fuel molecule gives an estimate of how much energy is available. More highly reduced molecules require more oxygen during combustion and produce more energy.

20. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 20 Examples of cycloalkanes Cyclopentane C 5 H 10

21. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 21 The simplest alkene, ethylene

22. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 22 Saturated fats contain three alkane chains, unsaturated fats three alkene chains

23. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 23 Cis and trans refer to different geometries in two isomers

24. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 24 Trans Fatty Acids in Some Common Food Products

25. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 25 The formation of trans double bonds, hydrogenation

26. Polymerization: white plastic water bottles Credit: Courtesy of Nalgene monomers

27. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 27 The simplest alkyne, acetylene

28. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 28 Benzene Naphthalene, in mothballs Anthracene, in insecticides and wood preservatives Aromatics Compounds, Polycyclic Aromatic Hydrocarbons (PAH’s)

29. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 29 Bioaccumulation of Polycyclic Aromatic Hydrocarbons A process by which chemical contamination increases within organisms higher up the food chain.

30. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 30 Functional Groups are groups of atoms that contribute to the properties of an organic compound a.Organic Halides ex. CH 3 -X (X = Cl, Br, I, or F) b.Oxygen-Containing Functional Groups 1.Ethers 2.Aldehydes 3.Ketones 4.Carboxylic Acids 5.Esters

31. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 31 Functional Groups Nitrogen-Containing Functional Groups 1.Amines 2.Amides

32. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 32 Alcohols and Ethers An alcohol contains the hydroxyl (-OH) functional group. In an ether, an oxygen atom is bonded to two carbon atoms. –C–O–C–. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

33. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 33 Aldehydes and Ketones An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

34. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 34 Carboxylic Acids and Esters Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O ║ — C—OH An ester contains the carboxyl group between carbon atoms. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

35. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 35 Amines and Amides In amines, the functional group is a nitrogen atom. | —N — In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

36. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 36 Functional Groups

37. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 37 Functional Groups Cont.

38. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 38 Learning Check Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine or amide. 1)CH 3 ─CH 2 ─CH 2 ─OH 2) CH 3 ─O─CH 2 ─CH 3 3) CH 3 ─CH 2 ─NH 2 O O ║ ║ 4) CH 3 ─C─OH 5) CH 3 ─C─O─CH 3

39. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 39 Solution 1)CH 3 ─CH 2 ─CH 2 ─OHalcohol 2) CH 3 ─O─CH 2 ─CH 3 ether 3) CH 3 ─CH 2 ─NH 2 amine O O ║ ║ 4) CH 3 ─C─OH 5) CH 3 ─C─O─CH 3 carboxylic acid ester

40. Polymerization of Teflon

41. Teflon frying pan Credit: Royalty Free/Alamy

42. Problematic Organic Halides Are No Longer Widely Used

43. Examples of Polyhydroxy Alcohols

44. Examples of Phenols

45. Examples of Aldehydes

46. Acetone (A Ketone) is produced during normal metabolism of fats A common household Product: nail polish remover. Acetone can be produced during metabolism of fats, particularly in cases of starvation or serious diabetes.

47. Examples of Carboxylic Acids

48. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 48 Isomers a.Isomers have the same chemical formula but different arrangements of atoms. b.One type of isomers is a pair of enantiomers, molecules that are “handed”. c.Enantiomers often have different biological activities. Ex. Ethanol (C 2 H 5 O) vs. dimethyl ether or Octane (C 8 H 18 ) vs isooctane

49. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 49 Enantiomers Enantiomers are like a pair of gloves: similar shapes that have “handedness” and are Nonsuperimposable R vs S enantiomers

50. Copyright © Houghton Mifflin Company. All rights reserved. 7 | 50 Key Words Organic chemistry Hydrophobic Parent compound Derivative/analogue Hydrocarbons Alkanes Alkenes Alkynes Aromatic Saturated Cycloalkanes Unsaturated Cis isomer Trans isomer Polymer Monomer