To prepare phenyl benzoate from phenol and benzoyl chloride by Schotten Baumann reaction




Aim
:- 

To prepare phenyl benzoate from phenol and benzoyl chloride by Schotten Baumann reaction. 

Apparatus & Chemical Required:-
 
To prepare phenyl benzoate to phenol, you will need the following materials:
  1. Phenyl benzoate
  2. Water
  3. Sulfuric acid (H2SO4)
  4. Sodium hydroxide (NaOH)
  5. A round-bottomed flask
  6. A reflux condenser
  7. A heating source (such as a hot plate)


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Theory and principle:- 


Phenyl benzoate can be converted to phenol through the process of hydrolysis, which involves breaking down a compound by reacting it with water.Phenol react with an aromatic acid chloride in the presence of excess NaOH reaction at room temperature to form an ester is called as Schotten Bauman reaction. 

If Phenol is shaken with benzoyl Chloride and excess amount of sodium hydroxide solution it is benzolyted to give the ester, phenyl benzoate. The phenol is converted into ionic compound sodium phenoxide by dissolving it sodium hydroxide solution. 


 
General reaction :- 

Mechanism for this reaction:-

Procedure:- 

Here is the procedure you can follow:
  1. Set up the round-bottomed flask with a reflux condenser.
  2. Add a small amount of water (around 50 mL) to the flask.
  3. Add a small amount of sulfuric acid to the water. The amount of sulfuric acid should be equal to about 1/10th of the weight of the phenyl benzoate.
  4. Slowly add the phenyl benzoate to the flask, being careful to avoid splashing.
  5. Heat the mixture using the heating source until it reaches a boiling point.
  6. Slowly add sodium hydroxide to the mixture, being careful to avoid splashing. The amount of sodium hydroxide should be equal to about 1/2 of the weight of the phenyl benzoate.
  7. Allow the mixture to cool to room temperature.
  8. Separate the phenol from the mixture by carefully pouring the mixture through a filter.
  9. Wash the phenol with a small amount of water to remove any impurities.
  10. Collect the purified phenol and store it in a clean container.



Precaution-

This procedure can be dangerous, as it involves the use of hazardous chemicals. It is important to follow all safety guidelines and wear appropriate protective equipment.


1- Always wear gloves while handling chemicals. 
2- Wear goggles to protect Eyes 
3- Benzoyl chloride should be handled with care under a fumehood. 
4- Phenol is not only toxic but will cause serve burns
5- Use freshly prepared solution of NaOH. 

Result:- 

1- Yield of crystals =
 2- Colour of Crystal = colorless
 3- Observed melting point of crystals =
 4- Literature melting point of compound =

Question Asking In Exam :- 

Schotten-Baumann reaction :- 

The Schotten-Baumann reaction is a chemical reaction that converts amines to amides using formic acid or formamide as acylating agents. The reaction is named after German chemists Gustav Schotten and Paul Baumann, who reported it in 1906. The reaction is typically carried out in the presence of a base such as potassium carbonate or sodium hydroxide to neutralize excess formic acid and formamide formed during the reaction. The Schotten-Baumann reaction is useful for synthesizing amides from primary, secondary, and tertiary amines.

The general reaction equation for the Schotten-Baumann reaction is:


R-NH2 + HCOOH → R-CO-NH2 + H2O

Here, R represents a primary, secondary or tertiary alkyl group.


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Here are the viva questions with solutions for the preparation of phenyl benzoate from phenol and benzoyl chloride by Schotten-Baumann reaction:



1. What is the Schotten-Baumann reaction?



Solution: The Schotten-Baumann reaction is a chemical reaction used to prepare esters from phenols and acid chlorides.



2. How can phenyl benzoate be prepared from phenol and benzoyl chloride using the Schotten-Baumann reaction?



Solution: Phenyl benzoate can be prepared by reacting phenol with benzoyl chloride in the presence of pyridine as a catalyst.



3. What is the role of pyridine in the Schotten-Baumann reaction?



Solution: Pyridine acts as a catalyst and helps to facilitate the reaction between phenol and benzoyl chloride.



4. What is the structural formula of phenyl benzoate?



Solution: The structural formula of phenyl benzoate is C6H5COOC6H5.



5. What type of reaction occurs during the Schotten-Baumann reaction?



Solution: The Schotten-Baumann reaction involves a nucleophilic acyl substitution reaction.



6. What conditions are necessary for the reaction between phenol and benzoyl chloride?



Solution: The reaction requires a catalyst (pyridine), a solvent (such as dichloromethane), and a temperature range of 0-5°C.



7. How can the purity of phenyl benzoate be increased using the Schotten-Baumann reaction?



Solution: The purity of phenyl benzoate can be increased by recrystallizing the product from a suitable solvent, such as ethanol.



8. What are the properties of phenyl benzoate?



Solution: Phenyl benzoate is a white crystalline solid with a melting point of 69-70°C.



9. What are the applications of the Schotten-Baumann reaction?



Solution: The Schotten-Baumann reaction is used to prepare esters, which are important intermediates in the synthesis of various organic compounds.




10. What precautions should be taken during the reaction between phenol and benzoyl chloride?



Solution: The reaction should be carried out in a well-ventilated area, and the reactants and products should be handled with care, as they can be hazardous.




to prepare phenyl benzoate from phenol
schotten baumaan reaction and mechanism
phenol to phenyl benzoate
 

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