Carboxylic Acids

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

• 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

• 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

• 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

• 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

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 videos

http://www.youtube.com/watch?v=VM3teHj3ZgY&feature=related

• http://www.youtube.com/watch?v=AEmRfxxGGcE&feature=related

• 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)

• 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

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/ninjat

urtlepoodle-thumb.jpg

• 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

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

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

• 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)

• 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

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

– 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

Making CA’s

• CA’s are made by oxidation of primary alcohols• AlcoholAldehydeCA (the 3rd time you’ve seen this)

• Derivatives of the CA’s-things you can make from them:

1. Esters2. Acid halides3. Amides4. Acid anhydrides

• ** we’ll be doing a reaction for each of the 4 above

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

How CA salts are made

• Sodium hydroxide + benzoic acid

• Lithium hydroxide + acetic acid

• Potassium hydroxide + formic acid

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

Don’t forget

• Acetic acid=ethanoic acid

• Formic acid=methanoic acid

• Propionic acid=propanoic acid

• Butyric acid=butanoic acid

Salts to draw for fun

• Sodium benzoate• Lithium acetate• Potassium formate• Sodium acetate• Lithium formate• Potassium benzoate

• Go back and do rxns!

Esters!

• RCOOR’

• Esters are named in 2 parts-see board • Esterification=making esters

• CA + alcohol ester + water

• RCOOH + ROH RCOOR + HOH

• 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

• Esters react w/HOH in a rxn called hydrolysis– Ester + HOHCA + 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