Carboxylic Acids: Crash Course Organic Chemistry #30 - Free Educational videos for Students in K-12

Carboxylic Acids: Crash Course Organic Chemistry #30 - By CrashCourse

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00:0-1	You can review content from crash course Organic Chemistry with
00:02	the crash course app available now for android and IOS
00:05	devices . Hi , I'm dave okay Chakravarty and welcome
00:08	to Crash course Organic Chemistry . What's the connection between
00:11	the smells of feet ? Under arms , vomit and
00:14	goats ? Carb oxalic acids . The smell of feet
00:18	is partly due to the presence of ice oval eric
00:20	acid , which is produced by the bacteria living on
00:23	your foot . Skin bacteria also turned odorless underarm secretions
00:27	such as amino acids into malodorous molecules which include carbon
00:31	cilic acids . The stench of vomit is caused by
00:34	beauty ric acid produced by bacteria in our gut beauty
00:37	. Uric acid is also found in rancid butter ,
00:40	that's where its name comes from . And it's a
00:42	key part of the aroma of parmesan cheese . It's
00:45	also added to some brands of american milk chocolate to
00:47	give it a tangy flavor . Yes , I basically
00:50	just said that puke flavored chocolate exists and now it's
00:53	going to haunt me forever . And three car back
00:55	cilic acids take their common names from the latin word
00:58	for goats . Capra , OIC acid , cap ,
01:00	krilic acid and ca prick acid found in small amounts
01:04	and goat's milk and produced in larger amounts as the
01:06	milk ages . They contribute to that goatee stench .
01:10	Given these awful smells , you might wonder why we'd
01:13	want to work with carb oxalic acids at all .
01:16	But we can actually make some pretty nice smelling compounds
01:19	using carb oxalic acids as a starting point and we
01:23	can convert them into other useful compounds for organic synthesis
01:29	. Yeah , let's kick off by reminding ourselves how
01:39	we can make a carb oxalic acid for example ,
01:42	we can oxidize alcohols or Aldo hides with chronic acid
01:45	or another suitable oxidizing agent . We can also make
01:48	them from Green Yard agents reacting the Green Yard Re
01:51	agent with carbon dioxide gives a carb oxalate salt ,
01:54	which can be protein aided with acid to give a
01:56	carb oxalic acid . We can get a more specific
01:59	name for any carb oxalic acid by looking at its
02:01	structure using the number of carbons in the longest chain
02:04	and adding the suffix OIC acid . A carb oxalic
02:07	acid with two carbons is death in OIC acid ,
02:10	A carb oxalic acid with three carbons is propane OIC
02:12	acid and so on . So in the previous reaction
02:16	we made to metal propane OIC acid when it comes
02:18	to naming compounds , carb oxalic acids have the highest
02:21	priority among carbon containing functional groups . So say we
02:25	have a molecule containing both a key tone and a
02:27	car park silic acid group . The car back silic
02:30	acid forms the base name . We assign the carb
02:32	oxalic acid carbon the number one and the ketone gets
02:35	a prefix . An example of this is four oxo
02:38	Penton OIC acid , also known as levy Olynyk acid
02:41	, a compound used as a starting point for the
02:43	synthesis of some pharmaceuticals and industrial chemicals . This compound
02:47	, like many we've mentioned , has a systematic pack
02:50	name and a common name like how economic acid ,
02:53	the acid and vinegar has the common name acetic acid
02:57	. As you'd expect from all these names , car
02:59	back silic acid are acidic . If they have about
03:03	four carbons are fewer , they can dissolve in water
03:05	. The hydrogen in the ceo H . Part of
03:08	the structure will be partially ionized , forming a hydrogen
03:11	ion and leaving behind a car box . Late ion
03:14	. Specifically carb oxalic acids are weak acids because they
03:18	don't release hydrogen ions into solution as much as a
03:21	strong acid , like hydrochloric acid does The Ceo H
03:24	part of these structures allows inter molecular hydrogen bonds to
03:27	form between two acid molecules or an acid and water
03:31	. So carb oxalic acids have high boiling points and
03:35	all those with fewer than 10 carbons in a straight
03:37	chain are liquids at room temperature . We can react
03:40	shorter chain car park silic acid with sodium or potassium
03:43	hydroxide to form water soluble salts . To the hydroxide
03:46	ion grabs the proton from the carb oxalic acid group
03:49	, forming water and leaving a car box late ion
03:52	behind . In fact , even weak bases like ammonia
03:55	can pull off a hydrogen ion and form a car
03:57	box late ion . As we know from earlier episodes
04:00	, both hydroxide ions , an ammonia are good nuclear
04:02	files , which actually highlights an issue that can come
04:05	up in the lab . Most basic nuclear files tend
04:08	to deep protein a carb oxalic acids . So unlike
04:11	Aldo hides and key tones , we can't just use
04:13	a nuclear file to add groups to the carbondale carbon
04:16	here , we'll have to get a little more creative
04:17	with our chemistry . Before we tackle that problem though
04:20	, let's look at some other reactions . Carb oxalic
04:22	acids can undergo if we want to get back to
04:25	an alcohol from a car park silic acid , we
04:27	can use a reducing agent such as lithium aluminum hydride
04:30	. This is a powerful reducing agent . So after
04:33	the reaction we add a proton source very carefully to
04:37	react any unredacted lithium aluminum hydride and give our alcohol
04:41	a proton back . Another way to remove the car
04:43	back silic acid group has a very straightforward name .
04:46	D car box elation . This involves heating the carb
04:49	oxalic acid and replaces the car box silic acid group
04:52	with a hydrogen atom . So if we heat the
04:55	heck out of almost any car box silic acid ,
04:57	we can get it to D carb oxalate . And
05:00	this reaction happens really easily when you heat compounds that
05:03	have a carbon . He'll group one carbon away from
05:06	the car box silic acid group . However , sometimes
05:08	you don't want to get rid of the car box
05:10	silic acid group entirely . So there are also reactions
05:14	to convert it to other functional groups . In fact
05:17	, we can freshen up some of those bad smells
05:19	by converting carb oxalic acids into pleasant smelling esters by
05:23	fisher . A stare ification . This is an acid
05:25	catalyzed reaction of a car park silic acid with an
05:28	alcohol to form an ester esters are often key parts
05:31	of the smells of flowers and fruits and are commonly
05:34	used in perfumes . Fisher a stare ification can also
05:37	be classified as a type of condensation reaction because the
05:40	two reactions kick out a water molecule when they combine
05:43	to get more specific first , the carbondale oxygen grabs
05:47	a proton from the acid catalyst . Next the lone
05:50	pair on the alcohol oxygen acts as a nuclear file
05:53	attacking the carbonell carbon . Another alcohol molecule swoops in
05:57	deep , resonating the hydrogen from the oxygen iem ion
06:00	in that 12 punch of attack . Then discrimination .
06:02	We're getting familiar with the O . H . Group
06:05	on the car back . Silic acid finds a hydrogen
06:07	ion from the acid catalyst , which makes water a
06:10	good leaving group . With a little help from the
06:12	neighboring oxygen atom in the molecule , the water leaves
06:15	and finally another alcohol molecule from solution grabs the extra
06:20	hydrogen on the carbon oxygen , giving us an ester
06:23	as our final product . All of these steps are
06:25	reversible so the product isn't formed super efficiently , but
06:30	never fear . Last shot leah is here . We
06:33	have the power to adjust the equilibrium of chemical reactions
06:37	. Specifically , if we remove one of the products
06:39	along the way , we can push the reaction forward
06:42	in a lab , removing the water as it forms
06:45	using a special piece of equipment increases or yield of
06:48	the ester Speaking of tricky lab situations , How about
06:51	that problem ? We mentioned earlier the issue of nuclear
06:54	files discriminating carbon cilic acids instead of attacking the carbonell
06:58	carbon . To solve this problem , we can convert
07:01	the car back silic acid to a more reactive functional
07:04	group and acid chloride using either phosphorus Penta chloride or
07:08	thiamine chloride . And let's just go with phosphorus Penta
07:11	chloride . As our example , the reaction starts when
07:14	the lone pair of electrons on the carbondale oxygen forms
07:17	a bond with the phosphorus atom . With a little
07:19	help from the other oxygen in the molecule and kicks
07:22	a chloride ion off of phosphorus Penta chloride . The
07:24	chloride ion we kicked out in the previous step swoops
07:27	back and attacks the carbondale carbons . Then a very
07:30	stable double bond forms between the phosphorus and this oxygen
07:34	. This double bond is a big part of why
07:35	this reaction happens this way . Just like we saw
07:38	in the video reaction in episode 28 , specifically with
07:41	the formation of this bond , we lose chloride as
07:44	a leaving group , which pulls off the nearby hydrogen
07:47	to reform our carbon oxygen double bonds . This gives
07:50	us the acid chloride with hydrochloric acid in phosphorus oxy
07:53	chloride as the other products , acid chlorides along with
07:56	other car back silic acid derivatives are involved in many
07:59	useful reactions in organic chemistry . In fact , acid
08:03	chlorides were using the synthesis of the first mass produced
08:06	antibiotic penicillin , which is an important car box silic
08:09	acid in medicine . Throughout the rest of the crash
08:12	course , organic chemistry series will apply many of the
08:14	reactions we learned to explore the chemical synthesis of penicillin
08:17	, but penicillin was an accidental discovery , Not a
08:21	medicine dreamed up by humans , and the story of
08:24	this compound is much more complicated than just one scientist
08:28	making a lucky discovery in 1928 . Let's head to
08:31	the thought bubble to learn more . Returning to his
08:33	lab after a summer holiday , the microbiologist alexander Fleming
08:37	discovered that one of his Petri dishes of bacteria had
08:40	been unintentionally left out on a bench . Spores of
08:42	the fungus had blown into the lab and contaminated the
08:46	dish and the temperatures have been perfect to encourage both
08:48	the fungus and the bacteria to grow . But wherever
08:52	the fungus had grown , the bacteria were absent ,
08:55	Fleming realized that the fungus made a chemical compound that
08:58	killed the bacteria . The fungus was from the genus
09:01	Penicillium . So Fleming named this mysterious compound penicillin ,
09:06	but despite many attempts , he was unable to isolate
09:09	it at Oxford University , a biochemist named ERnst Chain
09:13	found Fleming's publication on penicillin And suggested to a supervisor
09:17	Howard Florey that they try to isolate it . penicillin
09:21	was eventually isolated and purified in 1941 . That same
09:25	year , penicillin was first used to treat an infection
09:27	in a police officer . It was later hailed as
09:30	a wonder drug during World War II for its ability
09:32	to combat infections and wounded troops . But there was
09:35	still a huge unsolved problem in the early 1940s .
09:39	The low yield of penicillin from the mold . In
09:41	1943 , a bacteriologist named Mary Hunt made a breakthrough
09:45	while working at the US . Department of Agriculture's Northern
09:48	Regional Research Laboratory in Peoria Illinois , nicknamed moldy mary
09:52	. She hunted down moldy fruits and vegetables to test
09:55	for the presence of penicillin in the lab . A
09:58	spoiled cantaloupe melon had a fungus , Penicillium chris agena
10:02	that produced 200 times more penicillin than the fungus that
10:06	Fleming stumbled upon making mass production possible . Think stoppable
10:10	since mary Hunts cantaloupe discovery , we've learned a lot
10:14	more like the penicillin czar , actually a family of
10:17	compounds with different potency ease in ways to administer the
10:20	medicine . The penicillin that Fleming discovered and chain and
10:23	Florey isolated and even won a nobel prize for in
10:26	1945 . Was penicillin f the stuff that was produced
10:30	from hunt spoiled cantaloupe melon was penicillin . G in
10:34	later episodes will be looking at dr john C .
10:37	She hand synthesis of penicillin v which is the first
10:40	penicillin to be synthesized from scratch instead of extracted from
10:44	a fungus . The synthesis takes many steps . So
10:47	, over the course of the series will fill out
10:49	what we're calling our mold medicine map and we'll discover
10:52	how penicillin kills bacteria , all using organic chemistry .
10:56	In this episode we reviewed the reactions that form carb
10:59	oxalic acids , recap nomenclature and explain the properties of
11:03	carb oxalic acids , reacted carb oxalic acids to form
11:07	salts and formed esters and acid chlorides from carb oxalic
11:10	acids . In the next episode , we'll start looking
11:13	at how we can use carb oxalic acid derivatives to
11:15	get to other functional groups and see where some of
11:18	these reactions fit into our synthesis of penicillin . Until
11:21	then , thanks for watching this episode of Crash Course
11:23	Organic Chemistry . If you want to help keep all
11:25	Crash course free for everybody forever , you can join
11:28	our community on patreon . Mhm .

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