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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic.

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Presentation on theme: "Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic."— Presentation transcript:

1 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.1 Alcohols, Phenols, Thiols, and Ethers 1

2 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alcohols An alcohol contains a hydroxyl group (–OH) that replaces a hydrogen atom in a hydrocarbon. A phenol contains a hydroxyl group (–OH) attached to a benzene ring. 2

3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Alcohols The names of alcohols in the IUPAC system replace the -e with -ol with common names use the name of the alkyl group followed by alcohol 3 FormulaIUPACCommon Name CH 4 methane CH 3 ─OHmethanolmethyl alcohol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OHethanolethyl alcohol

4 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Alcohols 4

5 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming of Alcohols Step 1 Name the longest carbon chain with the –OH group. Name an aromatic alcohol as a phenol. CH 3  CH 2  CH 2  OH propanol OH CH 3  CH  CH 2  CH 3 butanol CH 3 OH CH 3  CH  CH 2  CH 2  CH  CH 3 hexanol

6 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming of Alcohols Step 2 Number the chain starting at the end closer to the –OH. CH 3  CH 2  CH 2  OH 1-propanol OH CH 3  CH  CH 2  CH 3 2-butanol CH 3 OH CH 3  CH  CH 2  CH 2  CH  CH 3 2-hexanol

7 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming of Alcohols Step 3 Give the location and name of each substituent relative to the –OH group. CH 3  CH 2  CH 2  OH 1-propanol OH CH 3  CH  CH 2  CH 3 2-butanol CH 3 OH CH 3  CH  CH 2  CH 2  CH  CH 3 5-methyl-2-hexanol

8 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Some Typical Alcohols OH | “Rubbing alcohol”CH 3 —CH—CH 3 2-propanol (isopropyl alcohol) Antifreeze HO—CH 2 —CH 2 —OH 1,2-ethanediol (ethylene glycol) OH | GlycerolHO—CH 2 —CH—CH 2 —OH 1,2,3-propanetriol 8

9 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Name the following compounds: 1. CH 3 —CH 2 —CH 2 —CH 2 —OH OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH

10 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 1 Name the longest carbon chain with the – OH group. Name an aromatic alcohol as a phenol. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 pentanol 3.cyclopentanol 10

11 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 2 Number the chain starting at the end closer to the – OH. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 2-pentanol 3. cyclopentanol 11

12 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 3 Give the location and name of each substituent relative to the – OH group. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 3-methyl-2-pentanol 3.cyclopentanol 12

13 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Phenols in Medicine Phenol is the IUPAC name for benzene with a hydroxyl group used in antiseptics and disinfectants 13 Phenol Resorcinol 4-Hexylresorcinol

14 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Derivatives of Phenol Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint. 14

15 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Phenols Step 1 Name the longest carbon chain with the – OH group. Name an aromatic alcohol as a phenol. 15 phenol phenol

16 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Phenols Step 2 Number the chain starting at the end closer to the – OH. 16 phenol phenol

17 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Phenols Step 3 Give the location and name of each substituent relative to the – OH group chlorophenol 4-bromophenol

18 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Write the structure of each of the following: A. 3-pentanol B. ethyl alcohol C. 4-methylphenol 18

19 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Write the structure of each of the following: A. 3-pentanol OH | CH 3 —CH 2 —CH—CH 2 —CH 3 B. ethyl alcohol CH 3 —CH 2 —OH C. 4-methylphenol 19 OH CH 3

20 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Thiols contain sulfur are similar to alcohols contain a thiol (–SH) group often have strong odors are found in cheese, onions, garlic, and oysters are used to detect gas leaks 20

21 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Thiols Thiols are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain. 21

22 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ethers An ether contains an – O – between two carbon groups has a common name that gives the alkyl names of the attached groups, followed by ether CH 3  O  CH 3 CH 3  CH 2  O  CH 3 22

23 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Write the structure of the following: A. 3-pentanol B. ethanethiol C. diethyl ether 23

24 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution OH | A. 3-pentanol CH 3  CH 2  CH  CH 2  CH 3 B. ethanethiol CH 3  CH 2  SH C. diethyl ether CH 3  CH 2  O  CH 2  CH 3 24

25 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ethers as Anesthetics Anesthetics inhibit pain signals to the brain like diethyl ether, CH 3  CH 2  O  CH 2  CH 3, were used for over a century, but caused nausea and were flammable developed by the 1960s were nonflammable Cl F F Cl F H H  C  C  O  C  HH  C  C  O  C  H F F F H F H Ethrane (enflurane) Penthrane 25

26 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.2 Properties of Alcohols and Ethers 26

27 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Classification of Alcohols Classification of alcohols is determined by the number of alkyl groups attached to the carbon bonded to the hydroxyl primary (1  ), secondary (2  ), or tertiary (3  ) Primary (1  ) Secondary (2  ) Tertiary (3  ) 1 group 2 groups 3 groups H CH 3 CH 3 | | | CH 3 —C—OH CH 3 —C—OH CH 3 —C—OH | | | H H CH 3 27

28 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Classify each alcohol as primary, secondary, or tertiary. OH | A. CH 3 —CH—CH 2 —CH 3 B. CH 3 —CH 2 —CH 2 —OH OH | C. CH 3 —CH 2 —C—CH 2 —CH 3 | CH 3 28

29 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution OH | A. CH 3 —CH—CH 2 —CH 3 secondary B. CH 3 —CH 2 —CH 2 —OH primary OH | C. CH 3 —CH 2 —C—CH 2 —CH 3 tertiary | CH 3 29

30 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility of Alcohols in Water Alcohols contain polar  OH groups and form hydrogen bonds with other alcohol molecules that have one to three carbons are soluble in water solubility in water decreases with increasing number of carbons 30

31 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility of Ethers in Water Ethers do not have a polar  OH group, but have a C  O  C group do not form hydrogen bonds with less than four carbons are slightly soluble in water with more than four carbons are not soluble in water 31

32 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility of Alcohols and Ethers in Water 32

33 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility of Phenols Phenols are slightly soluble in water have an  OH group that can form hydrogen bonds with water can react with water to produce phenoxide ions were once used as antiseptics 33 + H 2 O + H 3 O +

34 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Indicate whether each of the following is soluble in water and explain why. A. CH 3  CH 2  CH 2  CH 2  CH 2  CH 2  OH B. CH 3  O  CH 2  CH 3 C. CH 3  CH 2  OH 34

35 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Indicate whether each of the following is soluble in water and explain why. A. CH 3  CH 2  CH 2  CH 2  CH 2  CH 2  OH Not soluble Alcohols with long carbon chains (nonpolar) are not soluble. B. CH 3  O  CH 2  CH 3 Slightly soluble Ethers with less than four carbons are only slightly soluble in water. C. CH 3  CH 2  OH Soluble Short-chain alcohols form hydrogen bonds with water. 35

36 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.3 Reactions of Alcohols and Thiols 36

37 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Dehydration of Alcohols Alcohols undergo dehydration when heated with an acid catalyst the loss of –H and –OH from adjacent carbon atoms, producing an alkene H OH | | H +, heat H—C—C—H H—C=C—H + H 2 O | | H H H H alcohol alkene 37

38 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of 1  Alcohols Alcohols undergo oxidation, increasing the number of carbon and oxygen bonds. Primary alcohols are oxidized to produce an aldehyde. 1 bond to O 2 bonds to O H OH H O | | oxidation | || H—C—C—H | | | H H H 1  alcohol aldehyde 38

39 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of 1  Alcohols Alcohols undergo oxidation, increasing the number of carbon and oxygen bonds. Aldehydes can further oxidize to produce a carboxylic acid. 1 bond to O 2 bonds to O H O H O | || oxidation | || H—C—C—H H—C—C—OH | H aldehyde carboxylic acid 39

40 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of 2  Alcohols Secondary alcohols are oxidized to produce a ketone. To indicate the process of oxidation, [O] is placed over the reaction arrow. 1 bond to O 2 bonds to O H OH H H O H | | | [O] | || | H—C—C—C—H | | | | | H H H H H 2  alcohol ketone 40

41 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of Tertiary 3  Alcohols Tertiary (3  ) alcohols do not readily oxidize. OH CH 3  C  CH 3 [O]no product CH 3 no H to oxidize 3  alcohol no reaction 41

42 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation and Reduction In an oxidation, there is an increase in the number of C–O bonds there is a loss of H In a reduction, there is a decrease in the number of C–O bonds there is a gain of H 42

43 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation and Reduction 43

44 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Methanol Poisoning Methanol is also known as methyl alcohol is highly toxic and found in windshield washer fluid, Sterno, and paint strippers is rapidly absorbed and oxidized to formaldehyde and then formic acid O O [O] [O] CH 3 OH H  CH H  COH methyl alcohol formaldehyde formic acid 44

45 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ethanol, CH 3 CH 2 OH Ethanol acts as a depressant and kills or disables more people than any other drug is metabolized at a rate of 12–15 mg/dL per hour by a social drinker is metabolized at a rate of 30 mg/dL per hour by an alcoholic 45

46 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Effect of Alcohol on the Body 46

47 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of Thiols When thiols undergo oxidation, an H atom is lost from each of two –SH groups the product is a disulfide protein in hair is cross-linked by disulfide bonds found in the amino acid cysteine 47

48 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Select the product for the oxidation of OH [O] CH 3  CH  CH 2  CH 3 O A. CH 3  CH=CH  CH 3 B. CH 3  C  CH 2  CH 3 OH C. CO 2 + H 2 O D. CH 3  CH  CH 2  CH 3 48

49 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Select the product for the oxidation of OH [O] CH 3  CH  CH 2  CH 3 O The answer is B. CH 3  C  CH 2  CH 3 49

50 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Select the product when CH 3 –CH 2 –CH 2 –OH undergoes each of the following reactions: [O] [O] CH 3 —CH 2 —CH 2 OH B. C. 1) CH 3 —CH=CH 2 2) CO 2 + H 2 O O || 3) CH 3 —CH 2 —C—H O || 4) CH 3 —CH 2 —C—OH 50

51 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Select the product when CH 3 –CH 2 –CH 2 –OH undergoes each of the following reactions: O [O] B. 3) || CH 3 —CH 2 —CH 2 OH CH 3 —CH 2 —C—H [O] O C. 4) || CH 3 —CH 2 —C—OH 51

52 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Give the primary product for the reaction of 2-propanol when it undergoes A. oxidation B. dehydration 52

53 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution OH CH 3  CH  CH 3 = 2-propanol = C 3 H 8 O A. oxidation OH O [O] 2CH 3  CH  CH 3 + 9O 2 CH 3  C  CH 3 + 6CO 2 + 8H 2 O B. dehydration OH H +, heat CH 3  CH  CH 3 CH 3  CH=CH 2 + H 2 O 53

54 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.4 Aldehydes and Ketones 54

55 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Carbonyl Group in Aldehydes and Ketones A carbonyl group consists of a carbon-oxygen polar double bond has a very electronegative oxygen atom has two lone pair electrons on the O atom has partial positive charge on C and partial negative charge on O 55

56 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Carbonyl Group in Aldehydes and Ketones A carbonyl group in an aldehyde is attached to at least one H atom in a ketone is attached to two carbon groups 56

57 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Aldehydes An aldehyde has an IUPAC name in which the -e in the alkane name is changed to -al has a common name for the first four aldehydes that use the following prefixes: 1 carbon, form 2 carbons, acet 3 carbons, propion 4 carbons butyr followed by aldehyde 57

58 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Aldehydes 58

59 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Aldehydes 59

60 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Aldehydes 60 Give the IUPAC name for the following aldehydes: O || CH 3  CH 2  CH 2  CH  C  H | CH 3

61 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Aldehydes 61 Step 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with al. O || CH 3  CH 2  CH 2  CH  C  H | CH 3 pentanal benzaldehyde

62 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Aldehydes 62 Step 2 Name and number substituents by counting the carbonyl group as carbon 1. O || CH 3  CH 2  CH 2  CH  C  H | CH 3 2-methylpentanal 3,4-dichlorobenzaldehyde

63 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Aldehydes in Flavorings Several naturally occurring aldehydes are used as flavorings for foods and fragrances. 63

64 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Ketones When naming the following ketones in the IUPAC system, the -e in the alkane name is replaced with -one with a common name, the alkyl groups attached to the carbonyl group are named alphabetically, followed by ketone O O CH 3  C  CH 3 CH 3  C  CH 2  CH 3 propanone 2-butanone (dimethyl ketone) (ethyl methyl ketone) 64

65 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Ketones 65

66 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Ketones Name the following ketones using the IUPAC system. O || CH 3  CH 2  CH  CH 2  C  CH 3 | CH 3 66

67 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Ketones Step 1 Name the longest carbon chain that contains the carbonyl group by replacing the e in the alkane name with one. O || CH 3  CH 2  CH  CH 2  C  CH 3 | CH 3 hexanone 67 pentanone

68 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Ketones Step 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location. O || CH 3  CH 2  CH  CH 2  C  CH 3 | CH 3 2-hexanone 68 pentanone

69 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Ketones Step 3 Name and number any substituents on the carbon chain. O || CH 3  CH 2  CH  CH 2  C  CH 3 | CH 3 4-methyl-2-hexanone 69 2,3-dimethylcylcopentanone

70 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ketones in Common Use 70 Acetone (propanone) is a solvent used in nail polish remover. Butanedione is the butter flavoring used in margarine.

71 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Classify each as an aldehyde or ketone. O O || || A. CH 3 —CH 2 —C—CH 3 B. CH 3 —C—H CH 3 O | || C. CH 3 —C—CH 2 —C—H D. | CH 3 71

72 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Classify each as an aldehyde or ketone. O O || || A. CH 3 —CH 2 —C—CH 3 B. CH 3 —C—H CH 3 O | || C. CH 3 —C—CH 2 —C—H D. | CH 3 72 aldehyde ketone aldehyde ketone

73 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Classify each as an aldehyde, ketone, alcohol, or ether. O A. CH 3  CH 2  C  CH 3 B. CH 3  O  CH 3 CH 3 O OH C. CH 3  C  CH 2  C  HD. CH 3  CH  CH 3 CH 3 73

74 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Classify each as an aldehyde, ketone, alcohol, or ether. O A. CH 3  CH 2  C  CH 3 B. CH 3  O  CH 3 CH 3 O OH C. CH 3  C  CH 2  C  HD. CH 3  CH  CH 3 CH 3 74 aldehyde alcohol ketoneether

75 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Give the IUPAC name for each of the following ketones. O A. CH 3  CH 2  CH 2  CH 2  C  CH 3 O B. Cl  CH 2  CH 2  C  CH 3 75

76 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for each of the following ketones. Step 1Name the longest carbon chain that contains the carbonyl group by replacing the e in the alkane name with one. O A. CH 3  CH 2  CH 2  CH 2  C  CH 3 pentanone O B. Cl  CH 2  CH 2  C  CH 3 butanone 76

77 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for each of the following ketones. Step 2 Name the carbon chain starting from the end nearer the carbonyl group and indicate its location. O A. CH 3  CH 2  CH 2  CH 2  C  CH 3 2-pentanone O B. Cl  CH 2  CH 2  C  CH 3 2-butanone 77

78 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for each of the following ketones. Step 3Name and number any substituents on the carbon chain. O A. CH 3  CH 2  CH 2  CH 2  C  CH 3 2-pentanone O B. Cl  CH 2  CH 2  C  CH 3 4-chloro-2-butanone 78

79 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Give the IUPAC name for the following aldehyde compounds. O || A. CH 3 —CH 2 —CH 2 —C—H CH 3 O | || B. CH 3 —C—CH 2 —C—H | CH 3 79

80 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for the following aldehyde compounds. Step 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with al. O || A. CH 3 —CH 2 —CH 2 —C—Hbutanal CH 3 O | || B. CH 3 —C—CH 2 —C—Hbutanal | CH 3 80

81 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for the following aldehyde compounds. Step 2Name and number substituents by counting the carbonyl group as carbon 1. O || A. CH 3 —CH 2 —CH 2 —C—Hbutanal CH 3 O | || B. CH 3 —C—CH 2 —C—H3,3-dimethylbutanal | CH 3 81

82 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Draw the structural formulas for each: A. 4-methylpentanal B. 2,3-dichloropropanal C. 3-methyl-2-butanone 82

83 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Draw the structural formulas for each: CH 3 O A. 4-methylpentanal CH 3  CH  CH 2  CH 2  C  H Cl O B. 2,3-dichloropropanal Cl  CH 2  CH  C  H CH 3 O C. 3-methyl-2-butanoneCH 3  CH  C  CH 3 83

84 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.5 Properties of Aldehydes and Ketones 84 In Tollens’ test, a silver mirror forms when the oxidation of an aldehyde reduces silver ion to metallic silver. The silvery surface of a mirror is formed in a similar way.

85 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Physical Properties The polar carbonyl group provides dipole-dipole interactions.  +  -  +  - C=O Because the electronegative oxygen atom forms hydrogen bonds with water molecules, aldehydes and ketones with one to four carbons are very soluble. 85

86 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility of Aldehydes and Ketones in Water 86

87 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility in Water The electronegative O atom of the carbonyl group of aldehydes and ketones forms hydrogen bonds with water. 87

88 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Indicate whether each is soluble or insoluble in water. A. CH 3 —CH 2 —CH 3 B. CH 3 —CH 2 —OH O || C. CH 3 —CH 2 —CH 2 —C—H O || D. CH 3 —C—CH 3 88

89 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Indicate whether each is soluble or insoluble in water. A. CH 3 —CH 2 —CH 3 insoluble B. CH 3 —CH 2 —OH soluble O || C. CH 3 —CH 2 —CH 2 —C—H soluble O || D. CH 3 —C—CH 3 soluble 89

90 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of Aldehydes Primary alcohols can be oxidized to aldehydes, which can be easily oxidized to carboxylic acids. Secondary alcohols can be oxidized to ketones, which cannot be further oxidized. 90

91 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Tollens’ Test In Tollens’ test, Tollens’ reagent, which contains Ag +, oxidizes aldehydes but not ketones. Ag + is reduced to metallic Ag, which appears as a “mirror” in the test tube. 91

92 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Tollens’ Test 92

93 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Benedict’s Test In Benedict’s test, Benedict’s reagent, which contains Cu 2+, reacts with aldehydes that have an adjacent OH group. 93

94 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Benedict’s Test In Benedict’s test, an aldehyde is oxidized to a carboxylic acid, while Cu 2+ is reduced to give red Cu 2 O(s). 94 The blue Cu 2+ in Benedict’s solution forms a brick-red solid of Cu 2 O in a positive test for many sugars and aldehydes with adjacent hydroxyl groups.

95 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Reduction of Aldehydes and Ketones Aldehydes and ketones can be reduced by sodium borohydride, NaBH 4, or H 2. The reduction of aldehydes and ketones decreases the number of carbon–oxygen bonds by addition of hydrogen or loss of oxygen. 95

96 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Write the structure and name of the organic product when each is mixed with Tollens’ reagent. A. butanal B. acetaldehyde C. ethyl methyl ketone 96

97 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution A. O O || Tollens’ || CH 3 —CH 2 —CH 2 —C—OH butanal butanoic acid B. O O || Tollens’ || CH 3 —C—H CH 3 —C—OH acetaldehyde acetic acid C. Ethyl methyl ketone + Tollens’ No reaction Ketones are not oxidized by Tollens’ reagent. 97

98 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.6 Chiral Molecules 98

99 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Isomers Molecules are structural isomers when they have the same molecular formula, but different bonding arrangements. 99

100 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Stereoisomers Stereoisomers have identical molecular formulas, but they are not structural isomers. In stereoisomers, the atoms are bonded in the same sequence but differ in the way they are arranged in space. When stereoisomers have mirror images that are different, they are said to have “handedness.” 100

101 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chiral Molecules Have Handedness Chiral molecules have the same number of atoms arranged differently in space have one or more chiral carbon atoms, each of which is bonded to four different groups are like your hands Try to superimpose your thumbs, palms, back of hands, and little fingers. 101

102 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Some Everyday Chiral and Achiral Objects 102

103 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chiral Carbon Atoms Are Mirror Images The mirror images of chiral compounds cannot be superimposed. When the H and I atoms are aligned, the Cl and Br atoms are on opposite sides. 103

104 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Achiral Structures Are Superimposable When the mirror image of an achiral structure is rotated, the structure can be aligned with the initial structure. Thus this mirror image is superimposable. 104

105 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Identify each as a chiral or an achiral compound. 105 A. CH 2 CH 3 HCH 3 Cl C B. H HCH 3 Cl C C. Br HCH 3 Cl C

106 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Identify each as a chiral or an achiral compound. chiral achiral chiral 106 A. CH 2 CH 3 HCH 3 Cl C B. H HCH 3 Cl C C. Br HCH 3 Cl C

107 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Fischer Projections A Fischer projection is a two-dimensional representation of a three-dimensional molecule places the most oxidized group at the top uses vertical lines in place of dashes for bonds that go back uses horizontal lines in place of wedges for bonds that come forward 107

108 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Drawing Fischer Projections 108

109 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. D and L Notations By convention, the letter L is assigned to the structure with the –OH on the left. The letter D is assigned to the structure with the –OH on the right. 109

110 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Indicate whether each pair is a mirror image that cannot be superimposed (enantiomers). 110

111 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Indicate whether each pair is a mirror image that cannot be superimposed (enantiomers). Yes No 111

112 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Concept Map – Organic Molecules with O and S 112


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