1. ORGANIC CHEMISTRY Any molecule that contains the element CARBON

2. “ Natural” Products : Poison Ivy Poison Hemlock Snake Venom Tobacco "Organic" does not mean "natural."

3. Manmade Organic Substances

4. :Aromatic

5. HYDROCARBONS: “alk”- Only contain H ydrogen and C arbon Type of bond Between CARBONS determines the family Alk a ne = all single bond Alk e ne = double bond Alk y ne = triple bond

6. 6 Alkanes : general formula C n H 2n+2 Hydrocarbons CH 4 = methaneCH 4 = methane C 2 H 6 = ethaneC 2 H 6 = ethane C 3 H 8 = propaneC 3 H 8 = propane C 4 H 10 = butaneC 4 H 10 = butane C 5 H 12 = pentaneC 5 H 12 = pentane

7. HYDROCARBONS: Naming

9. ALKANES: name and formula

10. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 10 Structural Formulas Alkanes are written with structural formulas that are expanded to show each bond condensed to show each carbon atom and the attached hydrogen atoms

11. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 11 Draw the condensed structural formula for heptane. Heptane, an alkane, has seven carbon atoms in its carbon chain. CH 3 ─CH 2 ─CH 2 ─CH 2 ─CH 2 ─CH 2 ─CH 3

12. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 12 Name each of the following: A. CH 3 ─CH 2 ─CH 2 ─CH 3 B. CH 3 ─CH 2 ─CH 2 ─CH 2 ─CH 2 ─CH 2 ─CH 2 ─CH 3 four carbon atoms; butane eight carbon atoms; octane

13. 22.1 Hydrocarbons > 13 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. For the straight-chain alkanes with one to four carbon atoms, the official names and the common names are the same. For the chains longer than 4, the prefixes are pent- for 5, hex- for 6, hept- for 7, oct- for 8, non- for 9, and dec- for 10. Alkanes Straight-Chain Alkanes NameFormula MethaneCH 4 EthaneC2H6C2H6 PropaneC4H8C4H8 ButaneC 4 H 10 PentaneC 5 H 12 HexaneC 6 H 14 HeptaneC 7 H 16 OctaneC 8 H 18 NonaneC 9 H 20 DecaneC 10 H 22

14. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 14 Isomers of Butane Isomers have the same molecular formula have different atomic structure branched straight chain

15. 22.1 Hydrocarbons > 15 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The longest continuous carbon chain of a branched-chain hydrocarbon is called the parent alkane. All other carbon atoms or groups of carbon atoms are regarded as substituents. Atoms such as halogens, oxygen, and nitrogen can also be substituents.Alkanes Branched-Chain Alkanes

16. 22.1 Hydrocarbons > 16 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. A hydrocarbon substituent that is derived from an alkane is called an alkyl group. You can think of any alkyl group as just an alkane with one of the hydrogens removed. Alkyl groups are named by removing the -ane ending from the parent hydrocarbon name and adding -yl.Alkanes Branched-Chain Alkanes

17. 22.1 Hydrocarbons > 17 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The three smallest alkyl groups are the methyl group (–CH 3 ) the ethyl group (–CH 2 CH 3 ) the propyl group (–CH 2 CH 2 CH 3 ) When a substituent alkyl group is attached to a straight-chain hydrocarbon, branches are formed. An alkane with one or more alkyl groups is called a branched-chain alkane.Alkanes Branched-Chain Alkanes

18. 22.1 Hydrocarbons > 18 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Examples of primary, secondary, tertiary, and quaternary carbons are labeled in the structural formulas below.Alkanes Branched-Chain Alkanes

19. 22.1 Hydrocarbons > 19 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The compound with the following structural formula can be used as an example.Alkanes Branched-Chain Alkanes

20. 22.1 Hydrocarbons > 20 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 1.Find the longest continuous chain of carbons in the molecule. This chain is considered the parent hydrocarbon. The longest chain is highlighted in the example. It contains seven carbon atoms. So, the parent hydrocarbon is heptane.Alkanes Branched-Chain Alkanes

21. 22.1 Hydrocarbons > 21 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 2.Number the carbons in the main chain in sequence. To do this, start at the end that will give the substituent groups attached to the chain the smallest numbers. Numbering the chain from right to left gives the substituents the lowest numbers (2, 3, and 4).Alkanes Branched-Chain Alkanes

22. 22.1 Hydrocarbons > 22 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 3.Add numbers to the names of the substituent groups to identify their positions on the chain. These numbers become prefixes to the name of the substituent group. The substituents and positions are 2-methyl, 3-methyl, and 4-ethyl.Alkanes Branched-Chain Alkanes

23. 22.1 Hydrocarbons > 23 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 4.Use prefixes to indicate the appearance of the same group more than once in the structural formula. Common prefixes are di- (twice), tri- (three times), and tetra- (four times). The two methyl groups are combined as 2,3- dimethyl in the name.Alkanes Branched-Chain Alkanes

24. 22.1 Hydrocarbons > 24 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 5.List the names of alkyl substituents in alphabetical order. For purposes of alphabetizing, ignore the prefixes di-, tri-, and so on. The 4-ethyl group is listed first, followed by the 2,3-dimethyl.Alkanes Branched-Chain Alkanes

25. 22.1 Hydrocarbons > 25 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 6.Combine all the parts and use proper punctuation. Write the entire name without any spaces. Use commas to separate numbers, and use hyphens to separate numbers and words. The correct name of the compound is 4- ethyl-2,3-dimethylheptane.Alkanes Branched-Chain Alkanes

26. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 26 Naming Alkanes

27. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 27 Give the IUPAC name of the Alkane CH 3 CH 3  CH 3 ─CH─CH─CH 2 ─CH 2 ─CH 3 STEP 1 Write the alkane name of the longest continuous chain of carbon atoms. hexane STEP 2 Number the carbon atoms starting from the end nearer a substituent. 1 2 3 4 5 6

28. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 28 Example of Naming an Alkane (continued) STEP 3 Give the location and name of each substituent as a prefix to the alkane name. CH 3 CH 3 methyl groups on carbons 2 and 3  CH 3 ─CH─CH─CH 2 ─CH 2 ─CH 3 1 2 3 4 5 6 2,3-dimethylhexane

29. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 29 Give the IUPAC name of CH 3  CH 3 ─CH 2 ─CH─CH─CH 3 STEP 1 Write the alkane name of the longest continuous chain of carbon atoms. pentane STEP 2 Number the carbon atoms starting from the end nearer a substituent. 5 4 3 2 1

30. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 30 Solution (continued) STEP 3 Give the location and name of each substituent as a prefix to the alkane name. CH 3  CH 3 ─CH 2 ─CH─CH─CH 3 5 4 3 2 1 3-methylpentane methyl on carbon 3

31. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 31 Give the IUPAC name for the following CH 3 | CH 3 ─CH 2 ─CH─CH 2 ─C─CH 2 ─CH 3 STEP 1 Write the alkane name of the longest continuous chain of carbon atoms. heptane STEP 2 Number the carbon atoms starting from the end nearer a substituent. 7 6 5 4 3 2 1 STEP 3 Give the location and name of each substituent as a prefix to the alkane name. 3-methylheptane methyl on carbon 3

32. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Drawing Alkane Formulas 32

33. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 33 Draw the condensed structural formula for 2-methylbutane STEP 1 Draw the main chain of carbon atoms. For but ane, there are four carbon atoms in the chain. C─C─C─C STEP 2 Number the chain and place the substituents on the carbons indicated by the numbers. CH 3  C─C─C─C 1 2 3 4 STEP 3 Add the correct number of hydrogen atoms to give four bonds to each C atom. CH 3  CH 3 ─CH─CH 2 ─CH 3

34. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Just as straight-chain and branched- chain alkanes can be either saturated or unsaturated, so can cyclic hydrocarbons. A cyclic hydrocarbon that contains only single bonds, and is therefore saturated is called a cycloalkane. Cyclic Hydrocarbons

35. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. A compound that contains a hydrocarbon ring is called a cyclic hydrocarbon. Many molecules found in nature contain cyclic hydrocarbons. Rings with five and six carbons are the most abundant.

36. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. To determine the IUPAC name of a cycloalkane, first count the number of carbons in the ring and assign the corresponding alkane name. Then simply add the prefix cyclo- to the alkane name. Cyclic Hydrocarbons Name: cyclopropane

37. 37 Alkenes: Compounds with C=C Double Bonds Alkenes : general formula C n H 2n

38. 38 Alkynes Alkynes have carbon-carbon triple bonds.Alkynes have carbon-carbon triple bonds. C 2 H 2 : name = ethyne

39. FAMILIES OF HYDROCARBONS: ALKANE, ALKENE, ALKYNE

41. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 41 Unsaturated Compounds: Alkenes and Alkynes have fewer hydrogen atoms attached to the carbon chain than alkanes are alkenes with C=C double bonds are alkynes with triple C ≡ C bonds

42. Saturated vs Unsaturated S aturated: all S INGLE BONDS Alkanes Unsaturated: double and/or triple bond(s) present. Alkenes Alkynes

43. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 43 Naming Alkenes and Alkynes

44. 22.2 Unsaturated Hydrocarbons > 44 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The chain is numbered so that the carbon atoms of the double bond have the lowest possible numbers. Substituents on the chain are named and numbered in the same way they are for alkanes.Alkenes

45. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 45 Naming Alkenes and Alkynes

46. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 46 Write the IUPAC name for the following CH 3 | CH 3 ─CH=C─CH 3 STEP 1 Name the longest carbon chain that contains a double or triple bond. butene STEP 2 Number the carbon chain starting from the end nearer the double or triple bond. 4 3 2 1 STEP 3 Give the location and name of each substituent as a prefix 2-methyl-2-butene

47. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 47 Write the IUPAC name for the following CH 3 ─CH─C  C─CH 3 STEP 1 Name the longest carbon chain that contains a double or triple bond. pentyne STEP 2 Number the carbon chain starting from the end nearer the double or triple bond. 5 4 3 2 1 STEP 3 Give the location and name of each substituent as a prefix 2-pentyne

48. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 48 Draw the condensed structural formula for 2-methyl-3-hexyne. STEP 1 Draw the main chain of carbon atoms. For 3-hexyne, there are six carbon atoms in the chain, with a triple bond between carbons 3 and 4, C─C─C ≡ C─C─C STEP 2 Number the chain and place the substituents on the carbons indicated by the numbers. CH 3  C─C─C ≡ C─C─C 1 2 3 4 5 6

49. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 49 Solution (continued) STEP 3 Add the correct number of hydrogen atoms to give four bonds to each C atom. CH 3  CH 3 ─CH─C ≡ C─CH 2 ─CH 3 1 2 3 4 5 6 2-methyl-3-hexyne

50. Special HYDROCARBONS bond Between CARBONS = family Alkane = all single bond Alkene = double bond Alkyne = triple bond  AROMATIC Hydrocarbons: contain benzene molecule

51. 22.4 Hydrocarbon Rings> 51 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Any compound not classified as an aromatic compound is an aliphatic compound. Alkanes, alkenes, alkynes, and cycloalkanes are aliphatic compounds. The properties of aromatic compounds are quite different from those of aliphatic compounds. Aromatic Hydrocarbons

52. 22.4 Hydrocarbon Rings> 52 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. An aromatic compound, or arene, is now defined as an organic compound that contains a benzene ring or other ring in which the bonding is like that of benzene. Aromatic Hydrocarbons

53. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 53 Aromatic Hydrocarbons Benzene is the simplest aromatic compound

54. 22.4 Hydrocarbon Rings> 54 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The benzene molecule is a six-membered carbon ring with one hydrogen atom attached to each carbon. This arrangement leaves one electron from each carbon free to participate in a double bond. –Two different structures with alternating double bonds can be written for benzene. The Structure of Benzene

55. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 55 Benzene is also represented as a hexagon with a circle drawn inside

56. 22.4 Hydrocarbon Rings> 56 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. However, the traditional structure, shown to the right in the series above, is used in this textbook. Remember, though, that each bond in the ring is identical. The Structure of Benzene Drawing a solid or dashed circle inside a hexagon represents how the electrons are distributed.

57. :Aromatic

58. Lab: building organic compounds