Reaction Of Phenol With Benzoyl Chloride To Give Phenyl Benzoate | How Do You Prepare Phenyl Benzoate From Phenol And Benzoyl Chloride?

We can make phenyl benzoate from phenol using a reaction called the Schotten-Baumann benzoylation.

Here’s how it works:

1. Phenol is first dissolved in sodium hydroxide. This creates sodium phenoxide, which is more reactive than phenol itself.
2. Next, we add benzoyl chloride. This reacts with sodium phenoxide, resulting in the formation of phenyl benzoate.

The Schotten-Baumann reaction is a useful way to make esters from phenols and acid chlorides. It’s a classic organic chemistry reaction and is commonly used in the laboratory.

Let’s dive a little deeper into the reaction mechanism:

Sodium phenoxide is a strong nucleophile, meaning it’s attracted to positively charged atoms. The benzoyl chloride molecule has a highly reactive carbonyl group, making it an excellent electrophile, meaning it’s attracted to negatively charged atoms.

When sodium phenoxide encounters benzoyl chloride, a nucleophilic attack occurs. The oxygen atom from sodium phenoxide attacks the carbon atom in the carbonyl group of benzoyl chloride. This forms a tetrahedral intermediate, which then quickly breaks down to form phenyl benzoate.

The Schotten-Baumann reaction is typically carried out in an aqueous solution and often requires the addition of a base, such as sodium hydroxide. The base helps to deprotonate the phenol and increase its nucleophilicity. It also helps to neutralize the hydrochloric acid byproduct formed in the reaction.

This reaction is a key example of how we can manipulate organic molecules to form new and valuable compounds. It’s a testament to the power of organic chemistry and its ability to create complex structures from simpler starting materials.

Okay, let’s dive into the reaction between benzene and benzoyl chloride.

Benzoyl chloride reacts with benzene in the presence of a Lewis acid catalyst like anhydrous aluminum chloride (AlCl3) to produce benzophenone. This reaction is a classic example of Friedel-Crafts acylation.

Here’s how it works:

1. The aluminum chloride acts as a catalyst: It coordinates with the carbonyl group of benzoyl chloride, making the carbon atom more electrophilic (electron-loving). This makes the carbonyl carbon more susceptible to attack by the electron-rich benzene ring.

2. Benzene attacks the electrophilic carbon: The pi electrons of the benzene ring attack the electrophilic carbon of the benzoyl chloride, forming a carbocation intermediate.

3. The intermediate rearranges: The carbocation intermediate is unstable and undergoes a rearrangement. This process involves the loss of a proton from the benzene ring, which results in the formation of a stable benzophenone.

Let’s break it down step-by-step:

Step 1: The reaction starts with the formation of a complex between the benzoyl chloride and the aluminum chloride. The aluminum chloride acts as a Lewis acid, accepting a pair of electrons from the carbonyl oxygen of the benzoyl chloride. This creates a more reactive benzoyl chloride species.

Step 2: The benzene ring, with its electron-rich pi system, is then attracted to the electrophilic carbon of the benzoyl chloride complex. The benzene ring attacks this carbon, leading to the formation of a carbocation intermediate.

Step 3: The carbocation intermediate is unstable and undergoes a rearrangement process. A proton (H+) is removed from the benzene ring, leading to the formation of a stable benzophenone molecule.

The overall reaction:

Benzene + benzoyl chloride → benzophenone

Important points to remember:

Friedel-Crafts acylation is a key reaction in organic chemistry: It is used to synthesize ketones from aromatic compounds.

Aluminum chloride is a powerful Lewis acid: It is essential for the reaction to proceed.

The reaction is typically carried out in anhydrous conditions: This is because water can deactivate the aluminum chloride catalyst.

I hope this explanation is helpful. Let me know if you have any further questions!

Phenyl benzoate is a white, powdery organic compound that’s classified as an ester. This interesting compound is created through a chemical reaction involving phenol, sodium hydroxide, and benzoyl chloride. While it’s solid at room temperature, it can transform into an oily liquid at a relatively low temperature.

Let’s dive a little deeper into the fascinating process of making phenyl benzoate. The reaction is essentially a esterification process, where phenol reacts with benzoyl chloride in the presence of a base, like sodium hydroxide. Here’s a breakdown of what happens:

Step 1: The sodium hydroxide reacts with phenol to form sodium phenoxide. This is an important step, as it makes the phenol more reactive. Think of it like adding a little extra “oomph” to the phenol to get the reaction going!

Step 2: The sodium phenoxide then reacts with benzoyl chloride to form phenyl benzoate and sodium chloride. The sodium chloride is a byproduct of the reaction and is usually removed by filtration.

The reaction is typically carried out in a solvent, like diethyl ether, to help the reactants mix and react more easily. The reaction is also often heated to speed up the process. The result is a mixture of phenyl benzoate and other byproducts. Phenyl benzoate is then purified by techniques like recrystallization or distillation to remove any impurities.

The synthesis of phenyl benzoate is a neat example of how organic chemistry can be used to create useful compounds. It demonstrates the power of understanding chemical reactions and how we can manipulate them to produce desired products.

Benzoyl chloride is a versatile reagent in organic chemistry, known for its reactivity with various functional groups. It readily reacts with alcohols to form esters and with amines to form amides. This is because the carbonyl group in benzoyl chloride is highly electrophilic, making it susceptible to nucleophilic attack.

Let’s break down these reactions:

Reaction with Alcohols:

When benzoyl chloride reacts with an alcohol, the alcohol’s oxygen atom attacks the carbonyl carbon of the benzoyl chloride. This results in the formation of an ester and the release of hydrogen chloride (HCl).

Reaction with Amines:

Benzoyl chloride reacts similarly with amines. The amine’s nitrogen atom attacks the carbonyl carbon, leading to the formation of an amide and the release of HCl.

Friedel-Crafts Acylation:

Benzoyl chloride also undergoes Friedel-Crafts acylation reactions with aromatic compounds. In these reactions, benzoyl chloride acts as an acylating agent, transferring the benzoyl group to the aromatic ring. This process requires a Lewis acid catalyst, such as aluminum chloride (AlCl3). The resulting product is a benzophenone derivative.

Understanding the Reactions:

These reactions are all examples of nucleophilic acyl substitution. The carbonyl carbon in benzoyl chloride is an electrophilic center that is susceptible to attack by nucleophiles, such as alcohols, amines, and aromatic rings. The reactions are typically carried out in the presence of a base to neutralize the HCl that is produced.

Examples of Benzoyl Chloride Reactions:

– Reaction with Ethanol: Benzoyl chloride reacts with ethanol to form ethyl benzoate, an ester commonly used in fragrances and flavorings.

– Reaction with Aniline: Benzoyl chloride reacts with aniline to form benzamide, an amide used in the production of polymers and pharmaceuticals.

– Friedel-Crafts Acylation of Benzene: Benzoyl chloride reacts with benzene in the presence of AlCl3 to form benzophenone, a ketone used in the production of plastics and dyes.

Conclusion:

Benzoyl chloride is a valuable reagent in organic synthesis due to its ability to participate in various nucleophilic acyl substitution reactions. Its reactivity with alcohols, amines, and aromatic rings allows for the formation of diverse and useful products, making it an important tool in the synthesis of esters, amides, and ketones.

You can think of the phenyl group as a benzene ring that’s missing a hydrogen atom. It’s like taking a methane molecule (CH₄) and removing a hydrogen to get a methyl group (CH₃). Similarly, you take a benzene molecule (C₆H₆) and remove one hydrogen to get a phenyl group (C₆H₅).

The phenyl group is a common functional group in organic chemistry. It’s often attached to other molecules, and it can influence the properties of those molecules. For example, the phenyl group can make a molecule more hydrophobic (water-repelling) or more aromatic.

Let’s dive a little deeper into the process of how benzene becomes phenyl.

Imagine benzene as a six-membered ring with alternating single and double bonds between the carbon atoms. Each carbon atom in the ring is also bonded to a hydrogen atom. Now, to form a phenyl group, you simply remove one of these hydrogen atoms. This leaves behind a carbon atom with a free valence, ready to bond with another atom or group.

The phenyl group is often depicted as a ring with a single line extending from one of the carbons. This line represents the bond that the phenyl group can form with another atom or group.

Here are some key points about the phenyl group:

* The phenyl group is a hydrocarbon group, meaning it is made up of only carbon and hydrogen atoms.
* The phenyl group is an aromatic group, meaning it has a special type of stability due to the delocalized electrons within the ring.
* The phenyl group is often found in organic compounds like benzene derivatives, phenols, and polymers.

Understanding how benzene becomes phenyl is crucial for grasping the structure and reactivity of many organic molecules. So, remember, it’s just a matter of removing a hydrogen atom from a benzene ring!

Phenyl benzoate is soluble in ethanol, ethyl ether, and chloroform. However, it is insoluble in water.

This solubility behavior is due to the non-polar nature of phenyl benzoate. Let’s break down why:

Phenyl benzoate’s Structure: It’s composed of a benzene ring (a very stable ring of six carbon atoms) attached to a benzoate group (a carboxyl group attached to a benzene ring). This structure is essentially a long chain of carbon and hydrogen atoms, creating a non-polar molecule.

Polar vs. Non-Polar Solvents: Water is a polar solvent, meaning it has a positive and negative end due to the uneven sharing of electrons between hydrogen and oxygen. Non-polar molecules like phenyl benzoate don’t have this separation of charge, making them incompatible with water.

“Like Dissolves Like”: This is a key principle in chemistry. Substances with similar polarities tend to dissolve in each other. Since ethanol, ethyl ether, and chloroform are also non-polar, they readily dissolve phenyl benzoate.

In essence, phenyl benzoate’s solubility reflects the fundamental interactions between molecules. Its non-polar nature means it will dissolve in non-polar solvents but not in polar solvents like water.

You can prepare benzene from phenol using a simple reaction with zinc dust. The reaction is actually quite straightforward.

Here’s how it works:

When you heat phenol with zinc dust, the phenol molecule reacts with the zinc to form benzene and zinc oxide (ZnO).

Here’s the breakdown of the reaction:

Phenol reacts with zinc dust at a high temperature.
* This reaction converts phenol into a phenoxide ion and a proton.
* The proton then accepts an electron from the zinc, forming a hydrogen radical.
* The hydrogen radical then reacts with another hydrogen radical to form hydrogen gas (H2).
* Finally, the phenoxide ion converts into benzene.

The overall reaction can be represented as follows:

C6H5OH (phenol) + Zn → C6H6 (benzene) + ZnO (zinc oxide)

This reaction is an example of a deoxygenation reaction where oxygen is removed from the phenol molecule to form benzene.

Let’s explore a bit further into how this reaction works:

The Role of Zinc Dust: Zinc dust acts as a reducing agent, meaning it readily donates electrons. In this reaction, the zinc donates electrons to the phenol molecule, causing it to lose oxygen.

The Mechanism: The reaction proceeds through a series of steps involving the formation of intermediates.

* Initially, the phenol molecule reacts with the zinc to form a phenoxide ion and a zinc-phenol complex.
* The zinc-phenol complex then undergoes a series of reactions involving electron transfer and bond breaking, eventually leading to the formation of benzene and zinc oxide.

Importance of Temperature: The high temperature is crucial for this reaction to proceed effectively. It provides the necessary energy to break the strong bonds in the phenol molecule and facilitate the electron transfer from zinc to phenol.

This reaction provides a useful way to synthesize benzene from phenol. It’s a common example of how to manipulate organic molecules to create new products.

Let’s talk about the reaction between phenoxide and benzoyl chloride. Phenoxide is a more reactive species than phenol, and it readily reacts with benzoyl chloride. This reaction forms phenyl benzoate, a solid compound.

Think of it like this: Phenoxide, with its negative charge, is more eager to react than phenol. Benzoyl chloride, with its reactive chlorine, is the perfect partner. Together, they create phenyl benzoate, a beautiful solid.

But here’s the thing, you have to mix them for a little while for the reaction to happen. Why? Because the reaction needs a little bit of time to get going. It’s like mixing ingredients for a cake – you need to let everything combine before it becomes delicious!

Imagine you have a mixture of phenoxide and benzoyl chloride. The phenoxide ion attacks the carbonyl carbon in the benzoyl chloride, kicking out the chlorine atom. This leads to the formation of a new bond between the phenoxide ion and the carbonyl carbon. This results in the formation of phenyl benzoate. The reaction is an example of a nucleophilic acyl substitution reaction, where the nucleophile (phenoxide) attacks the electrophilic carbonyl carbon of benzoyl chloride.

Now, how long does it take? About 15 minutes of shaking the mixture is usually enough for the reaction to complete. You’ll end up with a nice solid phenyl benzoate, which is a good sign that the reaction has worked.

In comparison to the reaction with benzoyl chloride, phenoxide can also react with other acylating agents, such as acid anhydrides. Acid anhydrides are molecules that contain two acyl groups, and they are also very reactive towards phenoxide. For example, ethanoic anhydride, which is a common acid anhydride, will react with phenoxide to form phenyl ethanoate (also known as phenyl acetate).

The reaction between phenoxide and acid anhydrides is similar to the reaction with benzoyl chloride. The phenoxide ion attacks the carbonyl carbon of the acid anhydride, kicking out an acyl group. This results in the formation of an ester, such as phenyl ethanoate.

The reactions between phenoxide and both benzoyl chloride and acid anhydrides are important in organic chemistry because they allow us to synthesize a variety of esters. Esters have many uses, including as flavorings, fragrances, and solvents. So next time you enjoy a delicious fruit flavor, you might be tasting an ester that was synthesized using a reaction with phenoxide!

Phenol reacts with Benzoyl chloride in the presence of aqueous

Solution. The correct option is A Phenyl benzoate. Suggest Corrections. 35. Similar questions. Q. Which one of the following product formed when the reaction of phenol with benzoyl chloride in the presence of alkali takes place? Q. Toulene reacts with Cl2 in BYJU’S

Benzoylation of phenol with benzoyl chloride in the presence

Benzoylation of phenol with benzoyl chloride in the presence of dilute `NaOH` gives phenyl benzoate. This reaction is an example of. YouTube

Experiment 10 Preparation of the benzoate of phenol.

Many phenols yield crystalline benzoyl derivatives with benzoyl chloride in the presence of sodium hydroxide (Schötten-Baumann method). Mechanism. Procedure: To the phenol (0.5 g) is added 5% sodium The Department of Chemistry, UWI

The reaction of phenol with benzoyl chloride to give

JEE Main 2013: The reaction of phenol with benzoyl chloride to give phenyl benzoate is known as: (A) Claisen reaction (B) Schotten-Baumann reaction (C Tardigrade

Other Reactions of Phenol – Chemistry LibreTexts

The phenoxide ion reacts more rapidly with benzoyl chloride than the original phenol does, but even so you have to shake it with benzoyl chloride for about 15 Chemistry LibreTexts

chemguide: CIE A level chemistry support: Learning outcome

In making phenyl benzoate from phenol and benzoyl chloride, the phenol is made into a better nucleophile by reacting it with sodium hydroxide solution to produce phenoxide chemguide

17.10: Reactions of Phenols – Chemistry LibreTexts

explain why phenols and phenoxide ions are very reactive towards electrophilic aromatic substitution (see Section 16.4 of the textbook). write an equation to illustrate the oxidation of a phenol or an arylamine to a Chemistry LibreTexts

Schotten – Baumann Reaction – Introduction, Examples,

The phenol and the base involved in the reaction condition react to give phenoxide ion. Afterward, the benzoyl chloride is attacked by a phenoxide ion. The Vedantu

17.10 Reactions of Phenols – Chemistry LibreTexts

explain why phenols and phenoxide ions are very reactive towards electrophilic aromatic substitution (see Section 16.4 of the textbook). write an equation to illustrate the oxidation of a phenol or an Chemistry LibreTexts

some more reactions of phenol – chemguide

In order to get a reasonably quick reaction with benzoyl chloride, the phenol is first converted into sodium phenoxide by dissolving it in sodium hydroxide solution. The chemguide