Carboxylic Acids

1
Carboxylic Acids

• A lot more than LSD
• http//www.bing.com/videos/watch/video/lsd-testing
  -british-troops/293b0d18353f1e55babd293b0d18353f1e
  55babd-280692392475?qlsd

2

• CAs are in foods w/sour or tart taste
• CAs contain 2 groups
• Carbonyl (mommy) hydroxyl (daddy)? carboxyl
  (baby)
• Naming CAs is easy-see board

3

• Lots of CAs have common names-why?
• Theyre 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?vUiJgsPUYahs
• http//www.youtube.com/watch?vHoV_Jt1o-j8

4

• Acetic acid-ethanoic
• Acetum is Latin for vinegar
• Romans used to carry vinegar in their canteens
  b/c vinegar doesnt go bad like HOH does
• Vinegar was act of compassion for Jesus
• Romans story-they didnt 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
• Its found in stale perspiration
• Its a lachrymator-very stanky
• YT use of butyric acid 2 min
• http//www.youtube.com/watch?v4KWFX4gc34khttp//w
  ww.youtube.com/watch?v4KWFX4gc34k

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 videos http//www.youtube.com/watch?vVM3t
  eHj3ZgYfeaturerelated
• http//www.youtube.com/watch?vAEmRfxxGGcEfeature
  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 moms 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?vG-t8RJBjZPofeature
  fvsr

9
What about those babies who cant 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/nin
  jaturtlepoodle-thumb.jpg

10

• 1/20,000 babies are born w/out lactase, tested
  for at birth
• What can be done?
• Dont 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 CAs

• Pocahontas used CAs
• 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 CAs

• Oxalic acid or ethanedioic acid-very toxic!
• Common in rhubarb
• plants you dont eat ex house plants
• Also found in tumbleweed
• dead cows
• Silly tumbleweed video
• http//www.youtube.com/watch?vrNVcSIZyBuE

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?vx4SuqG6Jz8Mfeature
  related 10 min
• http//www.youtube.com/watch?vH3TaJAO_Q-U 3 min
• http//www.youtube.com/watch?vveE9-mr0B6sfeature
  related 7 min
• http//www.youtube.com/watch?vnhP9KVnHbNkfeature
  related 3 min
• History channel-really long video
• http//www.youtube.com/watch?vKvAJRp4CXdU
• Malonic acid-propanedioic
• Neither one (malonic succinic) is toxic
• Why is oxalic acid toxic yet these arent?
• In the body, oxalic acid pulls Ca out of the body
  to form Ca oxalate and thats bad (insoluble and
  toxic)

14

• Tartaric Acid
• Its 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 CAs

• High boiling points-lots of H bonding
• Small CAs are stinky liquids-Larger CAs are
  waxy solids
• Organic acids (CAs) 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 CAs
• 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?vQ37BmKgzFPkfeature
  related
• Stearic acid-in lotions, derived from animal fats
• Na benzoate-preservative, inhibits mold growth

17
Making CAs

• CAs are made by oxidation of primary alcohols
• Alcohol?Aldehyde?CA (the 3rd time youve seen
  this)
• Derivatives of the CAs-things you can make from
  them
• 1. Esters
• 2. Acid halides
• 3. Amides
• 4. Acid anhydrides
• well be doing a reaction for each of the 4
  above

18

• Salts of CAs
• Big acids (gt8 Cs) 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 acids common name is used-but know
  both

21
Dont forget

• Acetic acidethanoic acid
• Formic acidmethanoic acid
• Propionic acidpropanoic acid
• Butyric acidbutanoic 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 ?
• Esterificationmaking 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 ones
  arent b/c they have big nonpolar Rs
• 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-vid
  eo.htm
• http//www.doctoroz.com/videos/panic-problems-mitr
  al-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-wh
  y-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
• NaOHlye
• Soft vs hard HOH