1. Chapter 12 Organic Compounds with Oxygen and Sulfur
12.1
Alcohols, Thiols, and Ethers

2. 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.

3. 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

4. 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─CH3 5-methyl-2-hexanol

5. 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

6. Learning Check Name the following compounds. 1. CH3—CH2—CH2—CH2—OH
OH CH3
| |
2. CH3—CH—CH—CH2—CH3 3.

7. Solution OH CH3 | | 2. CH3—CH—CH—CH2—CH3 3-methyl-2-pentanol
1. CH3—CH2—CH2—CH2—OH 1-butanol
OH CH3
| |
2. CH3—CH—CH—CH2—CH methyl-2-pentanol
cyclopentanol

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

9. Derivatives of Phenol
Compounds of phenol are the active ingredients in the essential oils of nutmeg, thyme, cloves, and vanilla. 9

10. Common Phenols/Alcohols10

11. Common Phenols/Alcohols11

12. Common Phenols 12

13. Herbicides produced by Phenols13

14. Naming Phenols To name a phenol
with two substituents, assign C-1 to the carbon attached to the –OH.
number the ring to give the lowest numbers. 1 1 3 4
3-chlorophenol bromophenol

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

16. Solution 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

17. 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

18. Thiols
are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain.
(Methyl Mercaptan) 18 18 18

19. 19

20. Striped Skunk (Mephitis mephitis) Thiols
E-2-buten-1-thiol %
3-methyl-1-butanethiol %
2-quinolinemethanethiol % 20

21. 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. 21

22. 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. 22

23. 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

24. 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
Propyl People Ether

25. 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 25

26. Chapter 12 Organic Compounds with Oxygen and Sulfur
12.2
Properties of Alcohols and Ethers 26 26

27. 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. 27 27

28. 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. 28 28

29. 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. 29 29

30. Comparing Boiling Points and Solubility
Copyright © by Pearson Education, Inc. 30 30

31. Chapter 12 Organic Compounds with Oxygen and Sulfur
12.3
Reactions of Alcohols and Thiols 31 31

32. Combustion of Alcohols
Alcohols undergo combustion with O2 to produce CO2 and H2O.
CH3—CH2—OH + 3O CO H2O + Energy 32 32

33. 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 33 33

34. Learning Check
Write the equations for the reaction of 2-propanol when it
undergoes
1. combustion.
2. dehydration. 34 34

35. Solution OH │ CH3─CH─CH3 = 2-propanol = C3H8O 1. combustion
2C3H8O + 9O CO H2O
2. dehydration
│ H+
CH3─CH─CH CH3─CH=CH2 + H2O 35 35

36. 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. 36 36

37. Oxidation and Reduction37 37

38. 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 38 38

39. 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. 39 39

40. Effect of Alcohol on the Body40 40

41. 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 41 41

42. 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 42 42

43. Chapter 12 Organic Compounds with Oxygen and Sulfur
12.4
Aldehydes and Ketones 43

44. 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. 44

45. 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) 45

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

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

48. Naming Aldehydes 48

49. Aldehydes in Flavorings
Several naturally occurring aldehydes are used as flavorings for foods and fragrances.
Benzaldehyde (almonds)
Cinnamaldehyde (cinnamon) 49

50. 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) 50

51. Ketones in Common Use Nail polish remover, solvent
Propanone, dimethylketone, acetone
Butter flavoring
(Butanedione) 51

52. Aldehydes & Ketones in Nature52

53. 53

54. 54

55. 55

56. 56

57. 57

58. Learning Check Name the following compounds: A. B.
2-pentanone; methyl propyl ketone
3,3-dimethylbutanal 58

59. Learning Check Draw the structural formulas for each:
A. 4-methylpentanal
B. 2,3-dichloropropanal
C. 3-methyl-2-butanone 59

60. Chapter 12 Organic Compounds with Oxygen and Sulfur
12.5
Properties of Aldehydes and Ketones
Hydrogen Bond
Hydrogen Bond
Acetaldehyde
Acetone 60

61. 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. 61

62. Comparison of Boiling Points62

63. 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 63

64. 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) 64

65. 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). 65

66. green  orange  red  brown
Increasing amounts of reducing sugar
green  orange  red  brown 66