Carboxylic Acid Derivative Reactions - Free Educational videos for Students in K-12

Carboxylic Acid Derivative Reactions - By The Organic Chemistry Tutor

Transcript


00:00	in this lesson , we're going to focus on reactions
00:03	associated with carbons like acid derivatives . So the first
00:07	thing you need to know is that an ASic alright
00:11	is more reactive then an acid anhydride and the acid
00:19	anhydride is more reactive than and Esther the ester and
00:29	a carbolic acid . They have about the same reactivity
00:34	. Now carpets look asset is more reactive than um
00:37	I'd and in a minute is more reactive than the
00:43	deep originated form of a carbon look acid . So
00:48	it's more reactive than the car box . Later on
00:51	now let's focus on reactions that produce carbon like acids
00:56	. So we're gonna start with an acid chloride .
00:59	If we add water to a carbon like acid derivative
01:03	, it's going to make a carbolic acid . The
01:08	leaving group C . L . Will pair up with
01:10	hydrogen atom from water given us HDL as a byproduct
01:15	and then we need to pair up these two parts
01:17	and that's going to give us the card is like
01:20	acid . So that's a quick way to determine what
01:23	the products will be in this reaction . Now the
01:27	acid chloride is more reactive , then the carpets look
01:33	acid . And so whenever you have the situation ,
01:37	whenever you have a reaction with a more reactive species
01:41	on the left , but a less reactive species on
01:44	the right , the position of equilibrium will always favor
01:50	the side with the species that is less reactive .
01:53	So the reaction is going to go in the direction
01:55	towards the less reactive species . In this case we
01:59	have a product favorite reaction . Let me give another
02:04	example . Now let's take another acid derivative in this
02:08	case the acid anhydride . And let's react it with
02:11	water . So we're going to pair up the leaving
02:17	group with the hydrogen . And so let's make it
02:21	an un symmetrical and hydrate . So these two will
02:26	get together and we're going to get propane OIC acid
02:31	. And then if we pair up these two we're
02:33	going to get another carbon like acid . And so
02:39	whenever you mix an asset and high track with water
02:42	you get two carbons . Look acids . Now the
02:46	acid anhydride is more reactive and then the car was
02:51	like acid , the carbolic acid is less reactive .
02:54	And so like the other reaction , this is a
02:58	product favorite reaction . Another way in which you can
03:05	make a carbon like acid is by reacting and Esther
03:09	with water . And so this is going to be
03:15	the side product . So if you add H with
03:19	O . C H three , You get a chance
03:21	zero CH 3 or if you want to you can
03:24	write it this way CH , three OH . So
03:29	that's an alcohol and then combining these two , that's
03:33	going to give us the card is like acid .
03:35	So any time you add water to one of the
03:38	carbolic acid derivatives , you're going to get a carbon
03:43	like acid , assuming that the derivative is not less
03:46	reactive in the water . Now the ester and the
03:51	carbolic acid they have the same reactivity , they're equally
03:57	reactive . And so therefore this reaction is an equilibrium
04:03	, it's reversible . So you can go to the
04:05	right or you can go to the left and to
04:07	speed up this reaction , you need a catalyst ,
04:10	typically an acid catalysts . Now because this reaction is
04:18	in equilibrium , you can cause it to go one
04:21	way by adjusting the concentration of the species in this
04:24	reaction . For example , if you increase the concentration
04:27	of water , you can drive the reaction towards the
04:30	right . Or if you increase the concentration of the
04:33	alcohol , you can drive the reaction towards the left
04:38	. So anytime you increase the concentration of a reactant
04:41	, you can drive it to the right . Or
04:44	if you increase the concentration of a product , you
04:46	can draw the reaction to the left based on a
04:49	leash Italians principle of equilibrium . Now let's go over
04:54	the mechanism for the first reaction between and acid chloride
04:58	and water . So feel free to pause the video
05:05	and try this mechanism if you want to . The
05:08	first step is that water is going to attack the
05:10	carbon , your group , the carbon or carbon has
05:14	a partial positive charge and the oxygen of water has
05:18	a partial negative charge . So the auction item is
05:22	attracted to the carbon atom of the acid chloride and
05:29	so the pie bon is gonna break . Given us
05:32	a tetra federal intermediate that looks like this . Mhm
05:42	. Now in the next step we need to use
05:43	a weak base to remove a hydrogen and so we
05:47	could use another water molecule to do that for us
05:52	by the way . This first step and the second
05:54	step is reversible . Now this tetra hydro intermediate is
06:03	unstable and so it's going to collapse . Now ,
06:07	what we need to determine is which group will leave
06:10	. Is it going to be the chlorine group or
06:12	the hydroxy group ? Hydroxide is a stronger base than
06:17	chloride . So it's a poor leaving group . Therefore
06:20	, see how is going to leave . So this
06:23	long period will reform the pie bod , expelling the
06:26	best leaving group in this tetra hydro intermediate . And
06:30	so that's how we can go from and ask the
06:33	chloride to a carbon like acid . Now let's focus
06:38	on reactions that produce acid anhydride . A simple way
06:43	to do this is to react to carbons like acid
06:47	molecules together . If you take out water and you
06:54	combine the left side and the right side , it's
06:57	going to give you the acid anhydride and a side
07:02	product is water . Now , acid and hydrates are
07:08	more reactive then carbolic acids , which are less reactive
07:17	. As a result , this is not a product
07:19	favorite reaction . The reactant are energetically favored . Now
07:26	in order to drive the reaction to the right ,
07:29	we need to add heat . Now here's what's gonna
07:33	happen once you add a heat , the water that
07:37	exists as a product when he did it can turn
07:40	into steam and it could leave the solution and so
07:44	as water leaves the solution , esteem . The concentration
07:48	of water in a solution decreases and based on the
07:52	fatalities principle of equilibrium . If you decrease the concentration
07:56	of a product , what's going to happen , we
07:59	know the reaction will shift to the right and so
08:02	you need to add heat or a dehydrating re agent
08:06	to basically try this reaction forward P 205 is an
08:11	example of a dehydrating re agent that you could use
08:14	in this case . Or you could just use heat
08:18	. So that's one way in which you can make
08:20	. And acid anhydride . Here is an example problem
08:30	. So here we have a molecule with two carbons
08:33	like acid functional groups facing each other . What's going
08:37	to happen if we had heat to it , go
08:41	ahead and predict the major product of this reaction .
08:45	So we know what's going to happen . Water is
08:48	going to be removed and so we're going to get
08:53	a sigh , click anhydride . And this in hydrate
08:58	is known as phallic and hydrate and we'll get water
09:11	as a side product . The reaction is known as
09:17	folic acid . And so anytime you have two carbons
09:22	like acid functional groups reacting with each other . And
09:26	if you use heat or a dehydrating agent and then
09:30	high tried will form now another way in which we
09:33	can make and anhydride is by reacting an acid chloride
09:41	with a carbon look acid . So in this case
09:50	HDL is going to be the byproduct . Now this
09:54	reaction is favorable because room temperature hcls gas and so
09:59	it's going to leave this solution so the concentration of
10:03	a product is going down . Therefore this will dry
10:07	the reaction towards the right . So now all we
10:11	need to do is combine these two and our main
10:13	product will be economic and hydrate . So that's another
10:21	way in which you can make an and hydrate is
10:23	by reacting those two together .

Summarizer

DESCRIPTION:

This organic chemistry video tutorial provides a basic introduction into carboxylic acid derivative reactions. It explains how to interconvert acid chlorides, carboxylic acids, acid anhydrides, esters, and amides from one form to another. This video contains plenty of examples and practice problems.

OVERVIEW:

Carboxylic Acid Derivative Reactions is a free educational video by The Organic Chemistry Tutor.

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