What major organic product would you expect to obtain when...

Key Concepts

Nucleophilic Acyl Substitution

This is a key reaction mechanism for acyl chlorides in which a nucleophile attacks the electrophilic carbonyl carbon, leading to the displacement of the chloride ion. This process underlies many transformations of acyl chlorides into other functional groups such as esters, amides, and carboxylic acids, and is fundamental to understanding reactivity in carbonyl chemistry.

Friedel-Crafts Acylation

This reaction involves the formation of an acylium ion from an acyl chloride (often facilitated by a Lewis acid catalyst) and its subsequent reaction with an aromatic compound via electrophilic aromatic substitution. The process introduces an acyl group onto the aromatic ring, forming aromatic ketones, and is widely used in synthetic organic chemistry for modifying aromatic substrates.

Lewis Acid Catalysis

Lewis acids, such as aluminum chloride, play a critical role in facilitating reactions like Friedel-Crafts acylation. They coordinate with the acyl chloride to form a more electrophilic species (typically an acylium ion), thereby promoting the subsequent attack by a nucleophile or an aromatic ring. This catalysis is essential for the activation of otherwise less reactive species in many organic transformations.

Transcript

00:04 Suppose we want to explore the reactions of acyl halides.

00:10 Well, let's try taking acetyl chloride, which is a really great example of the different reactions that in general acyl halides can have.

00:19 And let's see what a bunch of different reagents could do to it.

00:23 Let's start off with h2.

00:27 What do we think that is going to make? well, acyl halide is the strongest derivative of a carboxylic acid.

00:37 And typically when we see water and let's say it was accompanied with in a basic medium or an acidic medium, that would be a hydrolysis.

00:47 Well, acyl halide being as reactive as it is, is reactive enough to just create a carboxylic acid with just the presence of water.

01:02 And as a side product, it will make hcl.

01:10 Let's try another reagent.

01:14 Butyl lithium in excess.

01:18 What would that make? well, butyl lithium is just an organometallic.

01:26 That is one, two, three, four lithium in excess.

01:33 And if we were to react an organic, organometallic to this, well, we would get a symmetric alcohol.

01:48 And this part is a butyl and this part is also a butel.

01:55 And that would be whatever our chain we have there will be here and here.

02:01 And we'll make that into an alcohol.

02:09 What about this alcohol in the presence of puridine? well, this would make an ester because we have an acyl halide and we have an alcohol.

02:37 And this will just make an ester molecule.

02:45 And our side product would be an a puridinium salt.

03:00 And that will be our side product.

03:07 What about reacting it with ammonia in excess? well, we have an nh3 group, and we have an acyl halide.

03:23 And we know that this would make an amine.

03:32 So, when it comes down to it, the strongest or, yeah, the strongest carboxylic acid derivative can make any weaker carbonic acid derivative.

03:45 So you can make nitro groups, you can make amides, you can make esters, and you can make anhydrides by just using acyl chloride or any acyl halide.

03:58 So acetychloride can make any acetyl chloride can make any carboxyde.

04:04 Oxylacid derivative.

04:08 And if we were to react with this molecule in the presence of, well, this seems to be pretty similar to when reacting with benzene, or benzene reactions, right, with activating a deactivating group, well, if we think of instead of adding this to our ring system, we are adding the ring system to this, but it will have the same effect.

04:47 We would have two different products.

04:53 This would be one, and this would be another, because the methyl group is not hindered enough for the orthoposition to not occur.

05:13 It is not hindered, so the orthoposition would be a product that would be possible.

05:21 Let's try another example.

05:27 This one is lithium -aluminum hydride with turt butoxide.

05:43 What would this product be? well, there are two reactions that are common to all carboxylic acid derivatives, and that is hydrolysis of a carboxylic acid derivative to carboxylic acid, and the other is creating an aldehyde.

06:06 And depending on the strength of the derivative, different reagents would be required to produce an aldehyde...

Please give Ace some feedback