1. ORGANIC CHEMISTRY Any molecule that contains the element CARBON

2. SUBSTITUTED HYDROCARBONS

4. Substituted Hydro- carbons

5. 23.1 Introduction to Functional Groups 5 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. A functional group is a specific arrangement of atoms in an organic compound that identify it as part of a specific family. Note that the double and triple bonds of alkenes and alkynes are considered the functional groups. Organic compounds can be classified according to their functional groups.

6. Identify the Functional Gro up

7. 23.1 Introduction to Functional Groups 7 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. What is the general formula of a halocarbon ? A halocarbon is an organic compound that contains at least one covalently bonded fluorine, chlorine, bromine, or iodine atom.Halocarbons Chloromethane Chloroethene

8. 23.1 Introduction to Functional Groups 8 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. What do mouthwash, perfume, and hairspray have in common? They all contain an alcohol of some type. An alcohol is an organic compound with an —OH group.Alcohols Ethanol

9. 23.1 Introduction to Functional Groups 9 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Interpret Data

10. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 10 Compounds with Oxygen Atoms Alcohols contain a hydroxyl group (-OH) Phenols contain a benzene ring with a hydroxyl group.

11. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 11 Alcohols are named with an IUPAC name that replaces the e in alkane name with ol CH 4 methane CH 3 ─OH methanol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OH ethanol

12. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 12 Naming Alcohols

13. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 13 Name the following Alcohol CH 3 OH │ │ CH 3 ─CH─CH 2 ─CH 2 ─CH─CH 3 STEP 1 Name the longest carbon chain with the  OH group. A six-carbon chain attached to an  OH is hexanol

14. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 14 Naming an Alcohol (continued) STEP 2 Number the chain starting at the end closer to the  OH group. CH 3 OH │ │ CH 3 ─CH─CH 2 ─CH 2 ─CH─CH 3 6 5 4 3 2 1 STEP 3 Give the location and name of each substituent relative to the  OH group. 5-methyl-2-hexanol

15. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 15 Name the following: STEP 1 Name the longest carbon chain with the  OH group. A four-carbon chain attached to an  OH is butanol. STEP 2 Number the chain starting at the end closer to the  OH group. STEP 3 Give the location and name of each substituent relative to the  OH group. 2-methyl-1-butanol CH 3 │ CH 3 ─CH 2 ─CH ─CH 2 ─OH 4 3 2 1

16. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 16 Give the IUPAC name for the following: OH CH 3 | | CH 3 —CH—CH—CH 2 —CH 3 STEP 1 Name the longest carbon chain with the  OH group. A five-carbon chain attached to an  OH is pentanol. STEP 2 Number the chain starting at the end closer to the  OH group. 1 2 3 4 5 STEP 3 Give the location and name of each substituent relative to the  OH group. 3-methyl-2-pentanol

17. 23.3 Carbonyl Compounds > 17 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The general formula of a carboxylic acid is RCOOH. Carboxylic Acids

18. 23.3 Carbonyl Compounds > 18 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The carboxylic acid CH 3 COOH is named ethanoic acid. Carboxylic Acids In the IUPAC system, carboxylic acids are named by replacing the -e ending of the parent structure with the ending -oic acid.

19. 23.3 Carbonyl Compounds > 19 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Interpret Data Some Saturated Aliphatic Carboxylic Acids Molecular formula Carbon atoms IUPAC name Common name Melting point (°C) HCOOH1Methanoic acidFormic acid 8 CH 3 COOH2Ethanoic acidAcetic acid 17 CH 3 CH 2 COOH3Propanoic acidPropionic acid –22 CH 3 (CH 2 ) 2 COOH4Butanoic acidButyric acid –6 CH 3 (CH 2 ) 4 COOH6Hexanoic acidCaproic acid –3 CH 3 (CH 2 ) 6 COOH8Octanoic acidCaprylic acid16 CH 3 (CH 2 ) 8 COOH10Decanoic acidCapric acid31 CH 3 (CH 2 ) 10 COOH12Dodecanoic acidLauric acid44 CH 3 (CH 2 ) 12 COOH14Tetradecanoic acidMyristic acid58 CH 3 (CH 2 ) 14 COOH16Hexadecanoic acidPalmitic acid63 CH 3 (CH 2 ) 16 COOH18Octadecanoic acidStearic acid70

20. 23.3 Carbonyl Compounds > 20 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Lemons and limes contain citric acid, a carboxylic acid that gives citrus fruits their sour flavor. Carboxylic Acids

21. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 21 Carboxylic acids are named in the IUPAC system by replacing the e in the alkane name of the longest carbon chain with oic acid H─COOH methanoic acidformic acid CH 3 ─COOH ethanoic acidacetic acid CH 3 ─CH 2 ─COOH propanoic acid CH 3 ─CH 2 ─CH 2 ─COOH butanoic acid

22. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Carboxylic Acids 22

23. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 23 Give the IUPAC name of the following Carboxylic Acid CH 3 | CH 3 —CH—CH 2 —COOH STEP 1 Identify the carbon chain containing the carboxyl group and replace the e in the alkane name with oic acid. butanoic acid

24. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 24 Example of Naming a Carboxylic Acid (continued) STEP 2 Give the location and name of each substituent on the main chain by counting the carboxyl group as carbon 1. CH 3 | CH 3 —CH—CH 2 —COOH 4 3 2 1 3-methylbutanoic acid

25. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 25 Give the IUPAC name for the following: CH 3 CH 3 | | CH 3 ─CH─CH 2 ─CH─COOH STEP 1 Identify the carbon chain containing the carboxyl group and replace the e with oic acid. pentanoic acid STEP 2 Give the location and name of each substituent on the main chain by counting the carboxyl group as carbon 1. 2,4-dimethylpentanoic acid 5 4 3 2 1

26. 23.3 Carbonyl Compounds > 26 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Aldehydes and Ketones What structural characteristic do an aldehyde and a ketone share? Aldehydes and Ketones A carbonyl group: it is a functional group with the general structure C O.

27. 23.3 Carbonyl Compounds > 27 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Some Common Aldehydes IUPAC name (common name) Structural formulaBall-and-stick model Methanal (formaldehyde) Ethanal (acetaldehyde) Benzaldehyde (benzaldehyde) Interpret Data

28. 23.3 Carbonyl Compounds > 28 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Some Common Ketones IUPAC name (common name) Structural formulaBall-and-stick model Propanone (acetone) Diphenylmethanone (benzophenone) Interpret Data

29. 23.3 Carbonyl Compounds > 29 Naming Aldehydes 29

30. 23.3 Carbonyl Compounds > 30 Give the IUPAC name for the following: Aldehyde Cl O │ ║ CH 3 ─CH 2 ─CH─CH 2 ─C─H STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with al. pentanal

31. 23.3 Carbonyl Compounds > 31 Aldehyde (continued) STEP 2 Name and number substituents by counting the carbonyl group as carbon 1. Cl O │ ║ CH 3 ─CH 2 ─CH─CH 2 ─C─H 5 4 3 2 1 3-chloropentanal

32. 23.3 Carbonyl Compounds > 32 Draw the condensed structural formula for 2,3-dichloropropanal. STEP 1 Draw the main chain of carbon atoms. Propanal has three carbon atoms with an aldehyde group. O ║ C─C─C─H 3 2 1 STEP 2 Number the chain and place the substituents on carbons indicated by the numbers.

33. 23.3 Carbonyl Compounds > 33 Solution (continued) Cl Cl O │ │ ║ C─C─C─H 3 2 1 STEP 3 Add the correct number of hydrogen atoms. Cl Cl O │ │ ║ CH 2 ─CH─C─H 2,3-dichloropropanal

34. 23.3 Carbonyl Compounds > 34 Naming Ketones In the name for a ketone, the IUPAC name replaces the e in the alkane name by one common name identifies the alkyl groups attached to the carbonyl group in alphabetical order and adds the word ketone

35. 23.3 Carbonyl Compounds > 35 Naming Ketones 35

36. 23.3 Carbonyl Compounds > 36 Give the IUPAC name for the following Ketone O ║ Cl─CH 2 ─CH 2 ─C─CH 2 ─Cl STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with one. butanone

37. 23.3 Carbonyl Compounds > 37 Example of Naming a Ketone (continued) STEP 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location. O ║ Cl─CH 2 ─CH 2 ─C─CH 2 ─Cl 4 3 2 1 STEP 3 Name and number any substituents on the carbon chain. 1,4-dichloro-2-butanone 2-butanone

38. 23.3 Carbonyl Compounds > 38 Give the IUPAC name for the following: CH 3 O │ ║ CH 3 ─CH 2 ─CH─C─CH 2 ─CH 3 STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with one. hexanone

39. 23.3 Carbonyl Compounds > 39 Solution STEP 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location. CH 3 O │ ║ CH 3 ─CH 2 ─CH─C─CH 2 ─CH 3 6 5 4 3 2 1 3-hexanone STEP 3 Name and number any substituents on the carbon chain. CH 3 O │ ║ CH 3 ─CH 2 ─CH─C─CH 2 ─CH 3 6 5 4 3 2 1 4-methyl-3-hexanone

40. 23.1 Introduction to Functional Groups 40 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. What is the general formula of an ether?Ethers An ether is an organic compound in which oxygen is bonded to two carbon groups.

41. 23.1 Introduction to Functional Groups 41 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Diethyl ether was the first reliable general anesthetic.Ethers However, because diethyl ether is highly flammable and often causes nausea, it was eventually replaced by other anesthetics.

42. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 42 Ethers contains an ─O─ between two carbon atoms has a common name of the two alkyl names followed by ether

43. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 43 Write the condensed structural formula of diethyl ether. This ether contains an ─O─ attached to two ethyl groups (CH 3 ─CH 2 ─ ). CH 3 ─CH 2 ─O─CH 2 ─CH 3

44. 23.3 Carbonyl Compounds > 44 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Esters are probably the most pleasant and delicious organic compounds one can study. Many esters have pleasant, fruity odors. Esters give blueberries, pineapples, apples, pears, bananas, and many other fruits their characteristic aromas. They also give many perfumes their fragrances.Esters

45. 23.3 Carbonyl Compounds > 45 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The general formula of an ester is RCOOR.Esters

46. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 46 Esterification is the reaction between a carboxylic acid and an alcohol uses an acid catalyst and heat O ║ H +, heat CH 3 — C—OH + HO—CH 2 —CH 3 O ║ CH 3 — C—O—CH 2 —CH 3 + H 2 O

47. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 47 Write the equation for the reaction of propanoic acid and methyl alcohol when heated in the presence of an acid catalyst. O ║ H +, heat CH 3 —CH 2 —C—OH + HO—CH 3 O ║ CH 3 —CH 2 —C—O—CH 3 + H 2 O

48. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 48 Esters In an ester, the H in the carboxyl group is replaced with an alkyl group. O ║ CH 3 —C—O—CH 3 ester group The ester methyl ethanoate (methyl acetate) is made from methyl alcohol and ethanoic acid (acetic acid).

49. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 49 The name of an ester includes name of the alkyl group from the alcohol the name of the carbon chain from the acid with the ic acid ending replaced by ate

50. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Esters 50

51. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 51 Example of Naming an Ester Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears: O ║ CH 3 —C—O—CH 2 —CH 2 —CH 3 STEP 1 Write the name of the carbon chain from the alcohol as an alkyl group. The alkyl group with three carbon atoms is propyl.

52. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 52 Example of Naming an Ester (continued) STEP 2 Change the ic acid of the acid name to ate. In the IUPAC name, ethanoic acid is named ethanoate. O ║ propyl CH 3 —C—O—CH 2 —CH 2 —CH 3 ethanoate propyl ethanoate (IUPAC) propyl acetate (common)

53. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 53 O ║ CH 3 —CH 2 —CH 2 —C—O—CH 2 —CH 3 Give the IUPAC for the following STEP 1 Write the name of the carbon chain from the alcohol as an alkyl group. STEP 2 Change the ic acid of the acid name to ate. O butanoate ║ ethyl CH 3 —CH 2 —CH 2 —C—O—CH 2 —CH 3 ethyl butanoate (IUPAC) ethyl

54. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 54 Draw the condensed structural formula of ethyl propionoate. O propionate ║ethyl CH 3 —CH 2 —C—O—CH 2 —CH 3

55. 23.1 Introduction to Functional Groups 55 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. What is the general formula of an amine?Amines An amine is an organic compound in which nitrogen is bonded to a carbon group. Ethanamine

56. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 56 Amines are derivatives of ammonia, NH 3 contain N attached to one or more alkyl or aromatic groups

57. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 57 Naming Simple Amines Simple amines have common names that list the alkyl groups attach to the N atom followed by amine.

58. 23.1 Introduction to Functional Groups 58 > Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. The -e ending of the parent hydrocarbon is changed to -amine. –Ethanamine is used to make plastics, pharmaceuticals, and pesticides. –Benzenamine is used to make furniture foam and some of the dyes that give clothes their colors.Amines Ethanamine Benzenamine

59. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 59 Learning Check Give the common name for each of the following: A. CH 3 —NH—CH 2 —CH 3 CH 3 | B.CH 3 —CH 2 —N—CH 2 —CH 3 ethylmethylamine diethylmethylamine

60. Basic Chemistry Copyright © 2011 Pearson Education, Inc. 60 Draw the condensed structural formulas for methylpropylamine CH 3 –CH 2 –CH 2 –NH–CH 3

61. 23.1 Introduction to Functional Groups 61 > Identify Family and Identify Family and Functional Group aldehyde Amine Alkene Ketone Acid Alkane

62. ester acid halogen alcohol halogen

63. Chapter 17 – Organic Chemistry 4. The IUPAC name for isopropyl alcohol is: A. 1–propanol B. 2–phenol C. 2–propanol D. 1,2,3–propanetriol C. 2–propanol

64. Chapter 17 – Organic Chemistry 5. The correct name of CH 3 -O-CH 2 CH 3 is: A. diethyl ether B. ethyl ether C. methyl ethyl ether D. ethyl methyl oxide C. methyl ethyl ether

65. Basic Chemistry Copyright © 2011 Pearson Education, Inc. Concept Map 65