1. Oxygen & Sulfur Compounds
Chapter 12:
Oxygen & Sulfur Compounds
Larry Emme
Chemeketa Community College

2. Chapter Outline Alcohols, Thiols, and Ethers
Properties of alcohols & Ethers
Reactions of Alcohols
Aldehydes & Ketones
Properties Carbonyls

3. Alcohols
An alcohol contains a hydroxyl group (—OH) attached to a carbon chain.
A phenol contains a hydroxyl group (—OH) attached to a benzene ring.

4. 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.
Formula IUPAC Common Name
CH4 methane
CH3─OH methanol methyl alcohol
CH3─CH3 ethane
CH3─CH2─OH ethanol ethyl alcohol

5. More Names of Alcohols
IUPAC names for longer chains number the chain from the end nearest the -OH group.
CH3─CH2─CH2─OH propanol OH │
CH3─CH─CH2─CH butanol
CH OH
│ │
CH3─CH─CH2─CH2─CH─CH methyl-2-hexanol 3 2 1 1 2 3 4 6 5 4 3 2 1

6. Some Typical Alcohols | “Rubbing alcohol” CH3—CH—CH3
2-propanol (isopropyl alcohol)
Antifreeze HO—CH2—CH2—OH
1,2-ethanediol (ethylene glycol)
Glycerol HO—CH2—CH—CH2—OH
1,2,3-propanetriol

7. Phenols in Medicine Phenol
Carbolic Acid
Phenol
is the IUPAC name for benzene with a hydroxyl group.
is used in antiseptics and disinfectants.
Phenol Resorcinol hexylresorcinol

8. Derivatives of Phenol
Compounds of phenol are the active ingredients in the essential oils of nutmeg, thyme, cloves, and vanilla. 8

9. Common Phenols/Alcohols

10. Common Phenols/Alcohols10

11. Common Phenols 11

12. Herbicides produced by Phenols12

13. Learning Check Write the structure of each of the following:
A pentanol
B. ethyl alcohol
C. para-methylphenol

14. Learning Check Answers
Write the structure of each of the following:
A. 3-pentanol OH |
CH3—CH2—CH—CH2—CH3
B. ethyl alcohol CH3—CH2—OH
C. para-methylphenol O H C 3

15. Thiols Thiols contain sulfur are similar to alcohols
contain a thiol (-SH) group
often have strong odors
found in cheese, onions, garlic, and oysters
are used to detect gas leaks

16. Thiols
are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain.
(Methyl Mercaptan) 16 16 16

17. 17

18. Striped Skunk (Mephitis mephitis) Thiols
E-2-buten-1-thiol %
3-methyl-1-butanethiol %
2-quinolinemethanethiol % 18

19. For pets that have been sprayed, bathe the animal in a mixture of 1 quart of 3% hydrogen peroxide (from drug store), 1/4 cup of baking soda (sodium bicarbonate) and a teaspoon of liquid detergent. After 5 minutes rinse the animal with water. Repeat if necessary. The mixture must be used after mixing and will not work if it is stored for any length of time. DO NOT STORE IN A CLOSED CONTAINER - it releases oxygen gas so it could break the container. This mixture may bleach the pet's hair. 19

20. Why tomato juice is believed to eliminate skunk odor
Why tomato juice is believed to eliminate skunk odor. Bathing an animal in tomato juice seems to work because at high doses of skunk spray the human nose quits smelling the odor (olfactory fatigue). When this happens, the odor of tomato juice can easily be detected. A person suffering olfactory fatigue to skunk spray will swear that the skunk odor is gone and was neutralized by the tomato juice. Another person coming on the scene at this point will readily confirm that the skunk spray has not been neutralized by the tomato juice. 20

21. Quickly And Safely Eliminates Odors On Pets
Thiotrol Spray is specially formulated to neutralize, not mask, offensive skunk odor on pets, people, clothing, carpets, and other contaminated surfaces.
Directions
Completely saturate affected areas with the high output pump sprayer. Work into fur, clothing, or carpet and allow to dry. Resaturate affected area and let dry. To avoid eyes, apply to face using a saturated cloth. Should any odors remain, locate odor source and reapply.
Thiotrol Spray Caution
For topical use only. Avoid contact with eyes.
Sold Exclusively Through Veterinarians

22. 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.
CH3─O─CH3 CH3─CH2─O─CH3
dimethyl ether ethyl methyl ether

23. Ethers as Anesthetics Anesthetics inhibit pain signals to the brain.
like diethyl ether, CH3─CH2─O─CH2─CH3, were used for over a century, but caused nausea and were flammable.
developed by the 1960s were nonflammable.
Ethrane (enflurane) Penthrane 23

24. Properties of Alcohols and Ethers24 24

25. Boiling Points of Alcohols
contain polar OH groups.
form hydrogen bonds with other alcohol molecules.
have higher boiling points than alkanes and ethers of similar mass. 25 25

26. Boiling Points of Ethers
do not have a polar group.
have an O atom, but there is no H attached.
cannot form hydrogen bonds between ether molecules. 26 26

27. Solubility of Alcohols and Ethers in Water
are more soluble in water than alkanes because the oxygen atom can hydrogen bond with water.
with 1-4 C atoms are soluble, but not with 5 or more C atoms.
Copyright © by Pearson Education, Inc. 27 27

28. Comparing Boiling Points and Solubility
Copyright © by Pearson Education, Inc. 28 28

29. Reactions of Alcohols and Thiols29 29

30. Combustion of Alcohols
Alcohols undergo combustion with O2 to produce CO2 and H2O.
CH3—CH2—OH + 3O CO H2O + Energy 30 30

31. Dehydration of Alcohols
Alcohols undergo
dehydration when heated with an acid catalyst.
the loss of —H and —OH from adjacent carbon atoms.
H OH
| | H+, heat
H—C—C—H H—C=C—H + H2O
| | | |
H H H H
alcohol alkene 31 31

32. 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. 32 32

33. Oxidation and Reduction33 33

34. Oxidation of Ethanol in the Body
enzymes in the liver oxidize ethanol.
the aldehyde produced impairs coordination.
blood alcohol over 0.4% can be fatal.
Ethyl alcohol Acetaldehyde Acetic acid 34 34

35. Ethanol, CH3CH2OH Ethanol acts as a depressant.
kills or disables more people than any other drug.
is metabolized at a rate of mg/dL per hour by a social drinker.
is metabolized at a rate of 30 mg/dL per hour by an alcoholic. 35 35

36. Alcohol Contents in Common Products
% Ethanol Product
50% Whiskey, rum, brandy
40% Flavoring extracts
15-25% ListerineTM, ScopeTM
20% Formula 44DTM
12% Wine, DristanTM
10% NyquilTM, CepacolTM
3-9% Beer, LavorisTM
60% ??? Hand Sanitizer
Hand sanitizer containing isopropyl alcohol (rubbing alcohol) is used in hand sanitizer. This alcohol is toxic and will damage your nervous system and internal organs if you drink it. Possible effects may include blindness, brain damage and kidney and liver damage, and death. 36 36

37. Oxidation of Thiols When thiols undergo oxidation,
an H atom is lost from each of two –SH groups.
the product is a disulfide.
[O]
CH3─SH + HS─CH CH3─S─S─CH3 + H2O 37 37

38. Aldehydes and Ketones 38

39. 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. 39

40. 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 prefixes: form (1C), acet (2C), propion (3C), and butyr (4C), followed by aldehyde.
Methanal Ethanal Propanal
(formaldehyde) (acetaldehyde) (propionaldehyde) 40

41. In a linear expression, the aldehyde group is often written as:
CHO

42. In the linear expression of a ketone, the carbonyl group is written as:CO

43. Naming Aldehydes 43

44. Aldehydes in Flavorings
Several naturally occurring aldehydes are used as flavorings for foods and fragrances.
Benzaldehyde (almonds)
Cinnamaldehyde (cinnamon) 44

45. Naming Ketones In naming 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.
Propanone butanone
(dimethyl ketone) (ethyl methyl ketone) 45

46. Ketones in Common Use Nail polish remover, solvent
Propanone, dimethylketone, acetone
Butter flavoring
(Butanedione) 46

47. Aldehydes & Ketones in Nature47

48. 48

49. 49

50. 50

51. 51

52. 52

53. Learning Check
Name the following compounds: A. B. 53

54. Learning Check Answers
Name the following compounds: A. B. 5 4 3 2 1
2-pentanone; methyl propyl ketone 4 3 2 1
3,3-dimethylbutanal 54

55. Learning Check Draw the structural formulas for each:
A. 4-methylpentanal
B. 2,3-dichloropropanal
C. 3-methyl-2-butanone 55

56. Learning Check Answers Draw the structural formulas for each:
A. 4-methylpentanal
B. 2,3-dichloropropanal
C. 3-methyl-2-butanone 56

57. Properties of Aldehydes and Ketones
Hydrogen Bond
Hydrogen Bond
Acetaldehyde
Acetone 57

58. Boiling Points + - + - + - Aldehydes and ketones have
polar carbonyl groups (C=O).
+ -
C=O
attractions between polar groups.
+  + -
C=O C=O
higher boiling points than alkanes and ethers of similar mass.
lower boiling points than alcohols of similar mass. 58

59. Comparison of Boiling Points59

60. Solubility in Water
The electronegative O atom of the carbonyl group of
aldehydes and ketones forms hydrogen bonds with water.
Hydrogen Bond
Hydrogen Bond
Acetaldehyde
Acetone 60

61. Tollens’ Silver Mirror 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.
Ag+ + e– → Ag(s) 61

62. Benedict’s Test In Benedict’s test,
Benedict’s reagent, which contains Cu2+, reacts with aldehydes that have an adjacent OH group.
an aldehyde is oxidized to a carboxylic acid, while Cu2+ is reduced to give brick red Cu2O(s). 62

63. green  orange  red  brown
Increasing amounts of reducing sugar
green  orange  red  brown 63

64. The End

65. End of Chapter Learning Checks Try these after you have reviewed the chapter

66. Learning Checks Name the following alcohol using the IUPAC method. 66

67. Learning Check Answers
Name the following alcohol using the IUPAC method.
5,5-dimethyl-3-heptanol 67 67

68. Learning Check Write the structural formula of 2,4-dimethyl-2-hexanol.68 68

69. Learning Check Answers
Write the structural formula of 2,4-dimethyl-2-hexanol. 69 69

70. Learning Check
Name the following phenol derivatives. 70 70

71. Learning Check Answers
Name the following phenol derivatives. 71 71

72. Learning Check
Give common names for the following ethers. 72 72

73. Learning Check Answers
Give common names for the following ethers. 73 73

74. Learning Check
Write the structure of butyl ethyl ketone. 74 74

75. Learning Check Answers
Write the structure of butyl ethyl ketone. 75 75

76. Learning Check
Give names for the following compounds. 76 76

77. Learning Check Answers
Give names for the following compounds.
2-methyl-6-bromo-4-octanone
2,4-dichloropentanal 77 77