ALCOHOLS!

1. ALCOHOLS! The –OH compounds 

2. Alcohols are compds containing –OH • -OH is called a hydroxy, hydroxyl, or hydric group • Naming alcohols is fun and easy! • Types of Alcohols: • Primary, secondary, tertiary, quaternary?

3. Alcohols are like water-both have –OH’s • HOH is polar (charged ends) • Alcohols (ROH) have a polar part (OH) and a nonpolar part (R) • big alcohols have big nonpolar parts and are less soluble in water • Small ones are more soluble b/c they are more like HOH • Alcohol and water can also be easily separated-how?

4. Hydrogen bonding in alcohols-what’s a H bond? • http://www.youtube.com/watch?v=cgiNk94XyaI • There are 2 H bonds in alcohols, 3 in water (draw) • The hydrogen bond isn’t real strong, but it IS important

5. Common Alcohols • Isopropyl alcohol (2-propanol) • Also called rubbing alcohol • Methanol or methyl alcohol (wood alcohol) made from distilling wood it’s a good fuel, toxic, causes blindness Video-blowing up methanol http://www.youtube.com/watch?v=kdDEDr3HX7Y

6. Ethanol/ethyl alcohol (grain alcohol) • Drinking alcohol • good fuel & antiseptic • made by fermentation • Fermentation involves 12 separate Rxns, each requiring an enzyme-yeast is the only known substance that contains all 12! • Typical fermentation reaction: Carbohydrate(sugar) + yeastCO2 + ethanol • Cool fermentation video 5min • http://www.youtube.com/watch?v=tNqfPsVAdYk

7. Where drinking alcohol comes from • Source alcohol • Taters vodka • Corn liquor • Rice sake • Molasses rum • Grapes wine

8. proof • Strength of alcohol is expressed in proof (2 x %) • Pure alcohol (PGA) is 200 proof • Drunk driving video 10 min • http://www.youtube.com/watch?v=5OBBqe6Wo1c&feature=PlayList&p=E5023B92BBF7FE7F&playnext=1&playnext_from=PL&index=42

9. 2 –OH alcohols: the Glycols • Antifreeze is best known glycol • Chemical names: ethylene glycol or 1,2-ethanediol (structure) • 100% soluble in water • Nonreactive,Very high bpt • Toxic! Shreds kidneys • Structure and stories

10. A safer (nontoxic) alternative antifreeze is propylene glycol • Chemical name: 1,2-propanediol • structure • It’s also a mucolytic-helps to decrease mucous, found in cough medicine

11. 3 –OH alcohols: the Glycerols Glycerols bind HOH & keep things moist Ex: lipstick, cake icing Glycerols are also used to preserve living tissues **gross cryonics video

12. Nitroglycerin is a glycerol • a powerful explosive, especially in liquid form • Used to make dynamite Video-the loaded goat http://www.youtube.com/watch?v=ozcMTuRWT6A&feature=PlayList&p=E81104CEDC532D8C&playnext=1&playnext_from=PL&index=21 http://www.youtube.com/watch?v=pTFNvslHNDc&feature=PlayList&p=E81104CEDC532D8C&playnext=1&playnext_from=PL&index=22 http://www.youtube.com/watch?v=FOxTDWtOlNo&feature=PlayList&p=E81104CEDC532D8C&playnext=1&playnext_from=PL&index=23 http://www.youtube.com/watch?v=DqCJ8t_5acc

13. Nitroglycerin story! • mid 1800’s-Alfred Nobel-his parents were in the nitroglycerin business. They sold nitro during wars & made $. Nitro was stored in a kitty-litter type of material b/c it’s so shock-sensitive. • One day, Alfred accidentally dropped a bottle of nitro-he hit the floor and covered his head!

14. Nitro story cont’d • But there was no explosion! The bottle had fallen into some of the kitty litter. Alfred decided to play. He got a funnel, dipped up the kitty litter, poured some of the nitro over it and left. When he came back, it had hardened. He poked it with a stick, hammered it, nothing happened. So he took it outside and blew it up. Dynamite was discovered.

15. Nobel invented dynamite-which made nitroglycerin safe and easy to handle. • So what about the Nobel Prize? • 1888-Nobel went out to get the paper, opened it up, and saw his own obituary! His brother had recently died, but they had made a mistake. The obit wasn’t complimentary! He felt so bad about it that he set up a fund with his royalties from dynamite and other inventions=the Nobel Prize!

16. More about dynamite • When dynamite gets old, it sweats. Miners used to wipe it off with their hands and throw it at the wall where it would blow up. • Nitro in very small amounts relaxes smooth muscle. Is used to treat Angina Pectoris-heart pain due to muscle spasms. It allows more O2 to come in. It now comes in patches and creams

17. Lab Methods of Preparing Alcoholsbut first-a prom story • 2 ways: • 1. Hydrolysis of alkyl halides • (rxn w/HOH-NOT addition of HOH) • CH3Cl + HOH CH3OH + HCl • OH switches with the halogen • 2. Hydration-addition of HOH to alkene • See board for ex rxn • Usually a secondary alcohol is produced in hydration-why?

18. Chemical Rxns of Alcohols • 1. Dehydration to give an alkene • See board • 2. Dehydration to give an ether • remove HOH from 2 molecules • *note the temp-it’s important!

19. 3. Oxidation Ex: • Ethanol (OA)ethanal + H2O • 2-propanol (OA)propanone + H2O H’s come from OH and top of same C, O comes from the OA Tertiary alcohols don’t oxidize-no H available **It’s important that some things don’t react-it’s a way to identify them

20. Important summary!! • Primary alcohols oxidize into Aldehydes • Secondary alcohols oxidize into Ketones • Tertiary alcohols don’t oxidize at all

21. Fun Reactions for Practice! • 1. Hydration of 1-pentene • 2. Hydrolysis of 2-chloropropane • 3. Dehydration of 1-butanol at 140 C. • 4. Dehydration of 1-butanol at 180 C. • 5. Hydration of cyclobutene. • 6. Oxidation of 1-butanol • 7. Oxidation of 2-butanol • 8. Dehydration of cyclopentanol at 140 C. • 9. Dehydration of cyclobutanol at 180 C. • 10. Hydrolysis of fluorocyclopropane

22. Procedure for distilling your apple juice  • 1. measure out 100 ml of your aj and put it into a 250 ml boiling flask • 2. set up distillation apparatus • 3. use small burner instead of HOH bath, don’t let temp get above 80C • 4. record ml collected-that’s the percent of alcohol • 5. multiply by 2-that’s the proof

23. The Ethers! • General formula is R-O-R’ • Simple vs. mixed ethers • Naming ethers! • Dimethyl ether • Ethyl methyl ether • Diisopropyl ether • Diethyl ether

24. Ethers are chemically inert-meaning? • “ether” is in starting fluid, anesthetics • ether is safe and easy to administer, but slow-acting, irritating to respiratory tract, and makes you throw up • Also extremely flammable! • Horace and Jasper discuss the use of ether • http://www.youtube.com/watch?v=bLm4VAyuKjg&feature=related

25. B/c of the problems with ether, many alternative anesthetics have been developed: • Divinyl ether-faster, less irritating, but more explosive • Some anesthetics aren’t ethers • Nitrous oxide-Mr. Nose! • Halothane-nonflammable, depresses cv/resp system Cyclopropane-30% He added b/c it’s so explosive • **Childbirth story • http://www.youtube.com/results?search_type=&search_query=anaesthesia+mavericks&aq=f

26. One “familiar” ether which is also a phenol is marijuana • Active ingredient is THC-tetrahydrocannabinol • Stay away from THC!!

27. The Phenols • These are the aromatic alcohols • Generally solids, water-soluble • Carbolic acid is aqueous phenol • Very corrosive, good germ killer • Dermatologists use it in dermabrasion-to peel off outside tissue • *romance novels story

28. Common Phenols • Creosote is the black, tarry stuff on RR crossties, telephone poles-good wood preservative • They used to wash dogs in creosote-why?

32. Phenols cont’d • Phenols are good germicides • what does “-icide” mean? • Ex: homicide, spermicide • 1864-Civil War just ended and a large # of people died from minor infections • Big problem!

33. Another story (Gary) • Late 1800’s-the British surgeon, Joseph Lister, noticed that many patients died even after minor surgery. One day while walking home, he passed a garbage dump. He said to himself, “Hmmm. This garbage smells a lot like my patients!” • He saw a bunch of guys spraying something on the garbage to keep the odor down-it was carbolic acid.

34. Story cont’d • Lister said, “Hey, I’m going to get some of that stuff to spray in my operating room!” He got so carried away, he started spraying the sheets, operating tools, and even his patients. And a crazy thing happened. His patients started living! He became known as “the Great Lister” • Listerine is named after him, but he didn’t invent it himself.

35. So how did we get Listerine? • Listerine contains: • Thymol-a good germicide • Menthol-gives it an icky taste • The 2 guys named their mouthwash after the Great Lister • *Mwash needs to stay in your mouth 30 secs minimum to be effective

36. More phenols • Resorcinol-in acne medicines • 4-n-hexyl resorcinol-in mouthwashes & to treat hookworm • Hexachlorophene-used in 1950’s-good bacteriacide-called Phisohex. • Drs used it as hand sanitizer • Now it’s banned  why? B/c . . . . .

37. More phenols • The French came out with a baby powder called Bebe’ which contained 8% hexachlorophene. • Unfortunately, infants started dying from weird neurological problems traced to the Bebe’ powder. • Now available by prescription only

38. More phenols • Pentachlorophenol-required coating on all exterior woodwork b/c kills mildew, bugs, and termites • Tetrahydrourushiol-irritant in poison ivy and poison oak. • nature story

39. Resveratrol-one of many phenols found in red wine-lowers bad cholesterol • BHT-butylated hydroxytoluene/ BHA-butylated hydroxyanisole • Found in cereal and other snacks-fat is oxidized easily and cereal becomes soft and yucky • BHT and BHA are antioxidants. They are sacrificial molecules. When O2 tries to attack your Lucky Charms, they say, “No! Take me! Take me instead!”

40. Why are antioxidants good? • RBC’s (red blood cells) have a fatty coating-vitamin C is an antioxidant that protects this coating • If a RBC is oxidized & broken down, you get anemia. • Vitamin C has its own protector-Vitamin E! • Natural antioxidants: vitamin C, vitamin E, Beta Carotene

41. Unicorn anesthetic • http://www.youtube.com/watch?v=oS3Olh9DnaE • Gibberish stuff • http://www.youtube.com/watch?v=ve0FQS1DLs4 • http://www.youtube.com/watch?v=P0gbOJbqcrE