What product forms when ethyl benzoate is treated with each of the following sets? (a) H2 O, N a

step 1 Okay, so we're reacting Ethel -Benz -O -8 with the following. And the structure of Ethel -Benz -

What product forms when ethyl benzoate is treated with each...

Key Concepts

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental mechanism in organic chemistry in which a nucleophile attacks the electrophilic carbonyl carbon of a carboxylic acid derivative (such as an ester), leading to the substitution of the original leaving group with the nucleophile. This mechanism underlies both saponification and acid-catalyzed ester hydrolysis.

Ester Hydrolysis

Ester hydrolysis is a reaction in which an ester is converted into a carboxylic acid and an alcohol by the addition of water. The process can be catalyzed either by acids or bases, with each pathway involving a nucleophilic attack on the carbonyl carbon and subsequent breakdown of the ester bond.

Saponification

Saponification is the base-catalyzed hydrolysis of an ester, where the reaction proceeds under basic conditions (typically NaOH) to form a carboxylate salt and an alcohol. This reaction is irreversible and is commonly used in soap making when triglycerides are converted to soap.

Acid-Catalyzed Hydrolysis

Acid-catalyzed hydrolysis involves the reaction of an ester under acidic conditions (using HCl, for example) where the ester is converted into a carboxylic acid and an alcohol. The reaction mechanism involves protonation of the carbonyl oxygen, which makes the carbonyl carbon more susceptible to nucleophilic attack by water.

Transcript

00:01 Okay, so we're reacting ethel -benz -o -8 with the following.

00:06 And the structure of ethel -benz -o -8.

00:09 So the o -8 implies it's the name for an ester, and ester is oxygen bound to a ketone.

00:21 The ethel group is attached to the oxygen.

00:24 And the benz -o -8, or the bends, is a benzene ring on the side.

00:35 And the structure is reacting with sodium hydroxide and water.

00:41 So it's under base conditions.

00:43 The oxygen of semi hydroxide is going to attack carbon carbon, giving us the alkoxid ion, the addition of oh -h.

01:08 Okay, so this bond is going to reform, and it's going to expel the ethoxide ion as opposed to hydroxide, because hydroxide is the stronger base.

01:35 So we get a carbosol acid, and we also have the athoxid ion, which is then going to de -perinate water.

01:44 We're just going to act as an acid here, and give us some of the carbonate acid our final product of benzok acid and ethanol and we also get sodium hydroxide back too because the oh h pairs up with sodium okay for b we have um ethylbenzoate reacting with water and hcdl so htl is going to be the acid and it's be the base so as a result if it's the acid it's going to give up its proton the oxygen and the ketune is going to depotinate the acid get this intermediate, positive charge, and as a result, it's going to make this carbon more electrophilic, so water is able to attack it.

03:26 It's been alcohol, and the addition of oh2.

03:32 So the oxygen of the ether here is going to deprotinate water, or just will have the proton transfer inside the reaction or inside the structure.

03:50 And once that occurs, it'll turn itself into better leaving group...

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