Carboxylic Acids

1. Carboxylic Acids A lot more than LSD http://www.bing.com/videos/watch/video/lsd-testing-british-troops/293b0d18353f1e55babd293b0d18353f1e55babd-280692392475?q=lsd

2. CA’s are in foods w/sour or tart taste • CA’s contain 2 groups: • Carbonyl (mommy) + hydroxyl (daddy) carboxyl (baby) • Naming CA’s is easy-see board

3. Lots of CA’s have common names-why? • They’re older than IUPAC • Most are derived from Latin names. • Formic acid is methanoic • Formica is Latin for ant (“ant” acid!) • Alchemists used to grind up ants & extract formic acid • Ant bite story, stupid lab aid story • YT ant videos • http://www.youtube.com/watch?v=UiJgsPUYahs • http://www.youtube.com/watch?v=HoV_Jt1o-j8

4. Acetic acid-ethanoic • Acetum is Latin for vinegar • Romans used to carry vinegar in their “canteens” b/c vinegar doesn’t go bad like HOH does • Vinegar was act of compassion for Jesus • Romans story-they didn’t have sugar. They boiled vinegar in their Pb (lead) pots and got a syrupy sweet toxic substance-lead acetate-one reason for decline of Roman Empire-insanity • only the rich influential rulers had lead pots

5. Butyric acid is butanoic • Butyrum is Latin for rancid butter • It’s found in stale perspiration • It’s a lachrymator-very stanky • YT use of butyric acid 2 min • http://www.youtube.com/watch?v=4KWFX4gc34khttp://www.youtube.com/watch?v=4KWFX4gc34k

6. The Goat Acids • Caproic is hexanoic • Caprylic is octanoic • Capric is decanoic • Caper is Latin for goat • These 3smell like a wet goat-secreted by goat skin • The Isle of Capris was once covered in goats • Capris pants? Also called clam-diggers • YT goat videoshttp://www.youtube.com/watch?v=VM3teHj3ZgY&feature=related • http://www.youtube.com/watch?v=AEmRfxxGGcE&feature=related

7. Lactic acid is 2-hydroxy propanoic acid • Lactis is Latin for milk • When milk sours it turns into lactic acid-gives a characteristic taste to yogurt and buttermilk • Lactic acid is also produced in the muscles during the breakdown of glucose-exercise burn • Baby intestines contain lots of lactic acid due to fermentation of mom’s milk by the bacteria lactobacillus-it helps prevent infections by suppressing growth of harmful bacteria which can lead to yeast infections (thrush)

8. People who are lactose intolerant can sometimes tolerate buttermilk and yogurt b/c the lactose has been converted into lactic acid • A sugar(lactose-ald) has oxidized into a CA(lactic acid)! • http://www.youtube.com/watch?v=G-t8RJBjZPo&feature=fvsr

9. What about those babies who can’t drink milk? • “Normal” babies are born w/the enzyme LACTASE allowing them to digest milk • Some babies are born w/out that enzyme. • What happens? • Malnourished • Galactose (toxic) builds up in blood, damages organs, causes cataracts • Galactoseuria-too much galactose in urine • Galactosemia-too much in the blood • http://wtfoodge.com/wp-content/uploads/2009/02/ninjaturtlepoodle-thumb.jpg

10. 1/20,000 babies are born w/out lactase, tested for at birth • What can be done? • Don’t drink milk, drink soy milk • Generally the condition is self-correcting by age 7 • The level of lactase drops as we age, so old people take Lactaid • In darker races, sometimes formerly healthy children 8-9 yrs old start having problems digesting milk • **there are 3500 enzymes in the body and a deficiency in even one of them causes problems • Chrysler union story

11. More CA’s • Pocahontas used CA’s • She gave John Smith bark from willow tree • Salicylic acid-long known as a pain reliever, but bad for stomach • Greeks, Romans got it from bark of willow tree-lots of willow trees in Italy • Bad beaver story

12. Di/Tri CA’s • Oxalic acid or ethanedioic acid-very toxic! • Common in rhubarb • & plants you don’t eat ex: house plants • Also found in tumbleweed • dead cows • Silly tumbleweed video • http://www.youtube.com/watch?v=rNVcSIZyBuE

13. Succinic acid-butanedioic • Latin succinum means amber • Amber is a tree sap, oozes out, hardens quickly. Bugs get caught in it. • Ex: Jurassic Park-looked for mosquito in amber, extract DNA and replicate dinosaur • History of the Shroud of Turin • http://www.youtube.com/watch?v=x4SuqG6Jz8M&feature=related 10 min • http://www.youtube.com/watch?v=H3TaJAO_Q-U 3 min • http://www.youtube.com/watch?v=veE9-mr0B6s&feature=related 7 min • http://www.youtube.com/watch?v=nhP9KVnHbNk&feature=related 3 min • History channel-really long video • http://www.youtube.com/watch?v=KvAJRp4CXdU • Malonic acid-propanedioic • Neither one (malonic & succinic) is toxic • Why is oxalic acid toxic yet these aren’t? • In the body, oxalic acid pulls Ca out of the body to form Ca oxalate and that’s bad (insoluble and toxic)

14. Tartaric Acid • It’s in cream of tartar, tartar sauce, grapes • Also found in wines when they age • Pasteur saw tartaric acid crystals in their 2 forms when he was drinking wine. Citric acid-a tricarboxylic acid-in fruits

15. Physical props of CA’s • High boiling points-lots of H bonding • Small CA’s are stinky liquids-Larger CA’s are waxy solids • Organic acids (CA’s) are weak acids • Meaning they ionize (break apart) only slightly in HOH • Strong acids (inorganics) ionize completely in HOH • Others-just for funstearic acid in waxes and chocolateCaprilic acid coconuts and breast milkLauric acid in Coconut oilMalic acid is found in apples

16. A few more CA’s • Folic acid-vit B complex, lack can cause birth defects such as anencephaly • Ascorbic acid-vit C-lack can cause scurvy • http://www.youtube.com/watch?v=Q37BmKgzFPk&feature=related • Stearic acid-in lotions, derived from animal fats • Na benzoate-preservative, inhibits mold growth

17. Making CA’s • CA’s are made by oxidation of primary alcohols • AlcoholAldehydeCA (the 3rd time you’ve seen this) • Derivatives of the CA’s-things you can make from them: 1. Esters 2. Acid halides 3. Amides 4. Acid anhydrides • ** we’ll be doing a reaction for each of the 4 above

18. Salts of CA’s • Big acids (>8 C’s) are generally insoluble in HOH • But when made into salts, they are very soluble • ****Neutralization • Acid + base  salt + HOH • drugs are salts • so are preservatives-check your Mt. Dew can • Fe is taken as a salt-Fe fumarate, Fe lactate • Ca lactate is a common way to give Ca Story-Kid who killed her dad w/the salt of a CA

19. How CA salts are made • Sodium hydroxide + benzoic acid  • Lithium hydroxide + acetic acid  • Potassium hydroxide + formic acid 

20. Naming CA salts • Positive ion comes first, ends in “ate” or “oate” • Show charges • Ex: • potassium formate • Sodium acetate • Lithium benzoate • Usually the acid’s common name is used-but know both

21. Don’t forget • Acetic acid=ethanoic acid • Formic acid=methanoic acid • Propionic acid=propanoic acid • Butyric acid=butanoic acid

22. Salts to draw for fun • Sodium benzoate • Lithium acetate • Potassium formate • Sodium acetate • Lithium formate • Potassium benzoate • Go back and do rxns!

23. Esters! • RCOOR’ • Esters are named in 2 parts-see board  • Esterification=making esters • CA + alcohol  ester + water • RCOOH + ROH  RCOOR + HOH

24. Esters have very low bpts-why? • No H bonds • Small esters are soluble in HOH, larger one’s aren’t b/c they have big nonpolar R’s • Esters smell good! • Isoamyl nitrate and nitroglycerin are esters • They called vasodilators-cause muscles lining the blood vessels to relax, & arteries to dilate (get bigger) • MVP story • Dr.Oz MVP video 6 min http://videos.howstuffworks.com/sharecare/31114-dr-oz-mitral-valve-disease-video.htm http://www.doctoroz.com/videos/panic-problems-mitral-valve-prolapse

25. Esters react w/HOH in a rxn called hydrolysis • Ester + HOHCA + alcohol • (backwards esterification) • When you use NaOH as a catalyst in hydrolysis, you can make soap! • How soap works 2 min video • http://videos.howstuffworks.com/discovery/38574-why-tell-me-why-soap-cleans-video.htm • Saponification (soap making) is the base-catalyzed hydrolysis of an ester • Dirty jobs making soap http://videos.howstuffworks.com/discovery/29911-dirty-jobs-soap-making-video.htm • NaOH=lye • Soft vs hard HOH