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

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Presentation on theme: "1 C hapter 12 Organic Compounds with Oxygen and Sulfur 12.1 Alcohols, Thiols, and Ethers."— Presentation transcript:

1 1 C hapter 12 Organic Compounds with Oxygen and Sulfur 12.1 Alcohols, Thiols, and Ethers

2 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 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. FormulaIUPACCommon Name CH 4 methane CH 3 ─OH methanol methyl alcohol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OH ethanol ethyl alcohol

4 4 More Names of Alcohols IUPAC names for longer chains number the chain from the end nearest 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 6 5 4 3 2 1

5 5 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

6 6 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 3 3.

7 7 Solution 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

8 8 Phenols in Medicine Phenol is the IUPAC name for benzene with a hydroxyl group. is used in antiseptics and disinfectants. Phenol Resorcinol 4-hexylresorcinol Carbolic Acid

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

10 10 Common Phenols/Alcohols

11 11 Common Phenols/Alcohols

12 12 Common Phenols

13 13 Herbicides produced by Phenols

14 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. 3-chlorophenol 4-bromophenol 3 4 1 1

15 15 Write the structure of each of the following: A. 3-pentanol B. ethyl alcohol C. para-methylphenol Learning Check

16 16 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. para-methylphenol OH CH 3

17 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 17

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

19 19

20 20 Striped Skunk (Mephitis mephitis) Thiols E-2-buten-1-thiol 38-44% 3-methyl-1-butanethiol 18-26% 2-quinolinemethanethiol 3-12%

21 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.

22 22 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.

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 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. CH 3 ─O─CH 3 CH 3 ─CH 2 ─O─CH 3 d imethyl ether ethyl methyl ether Propyl People Ether

25 25 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. Ethrane (enflurane) Penthrane

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

27 27 Boiling Points of Alcohols Alcohols contain polar OH groups. form hydrogen bonds with other alcohol molecules. have higher boiling points than alkanes and ethers of similar mass.

28 28 Boiling Points of Ethers Ethers do not have a polar group. have an O atom, but there is no H attached. cannot form hydrogen bonds between ether molecules.

29 29 Solubility of Alcohols and Ethers in Water Alcohols and ethers 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 © 2009 by Pearson Education, Inc.

30 30 Comparing Boiling Points and Solubility Copyright © 2009 by Pearson Education, Inc.

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

32 32 Combustion of Alcohols Alcohols undergo combustion with O 2 to produce CO 2 and H 2 O. CH 3 —CH 2 —OH + 3O 2 2CO 2 + 3H 2 O + Energy

33 33 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 + H 2 O | | H H H H alcohol alkene Dehydration of Alcohols

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

35 35 Solution OH │ CH 3 ─CH─CH 3 = 2-propanol = C 3 H 8 O 1. combustion 2C 3 H 8 O + 9O 2 6CO 2 + 8H 2 O 2. dehydration OH │ H + CH 3 ─CH─CH 3 CH 3 ─CH=CH 2 + H 2 O

36 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.

37 37 Oxidation and Reduction

38 38 Oxidation of Ethanol in the Body 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

39 39 Ethanol acts as a depressant. 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. Ethanol, CH 3 CH 2 OH

40 40 Effect of Alcohol on the Body

41 41 % EthanolProduct 50%Whiskey, rum, brandy 40%Flavoring extracts 15-25%Listerine TM, Scope TM 20%Formula 44D TM 12%Wine, Dristan TM 10%Nyquil TM, Cepacol TM 3-9%Beer, Lavoris TM Alcohol Contents in Common Products

42 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] CH 3 ─SH + HS─CH 3 CH 3 ─S─S─CH 3 + H 2 O

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

44 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.

45 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. M ethanal EthanalPropanal ( form aldehyde) ( acet aldehyde)( propion aldehyde)

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 48 Naming Aldehydes

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

50 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 2-butanone (dimethyl ketone) (ethyl methyl ketone)

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

52 52 Aldehydes & Ketones in Nature

53 53

54 54

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57 57

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

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

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

61 61 Boiling Points Aldehydes and ketones have polar carbonyl groups (C=O).  +  - C=O attractions between polar groups.  +  -  +  - C=O higher boiling points than alkanes and ethers of similar mass. lower boiling points than alcohols of similar mass.

62 62 Comparison of Boiling Points

63 63 The electronegative O atom of the carbonyl group of aldehydes and ketones forms hydrogen bonds with water. Solubility in Water Acetaldehyde Acetone Hydrogen Bond

64 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)

65 65 Benedict’s Test In Benedict’s test, Benedict’s reagent, which contains Cu 2+, reacts with aldehydes that have an adjacent OH group. an aldehyde is oxidized to a carboxylic acid, while Cu 2+ is reduced to give brick red Cu 2 O(s).

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


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