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Synthesis of Ethyl Acetate

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The key takeaways are that esters are produced from carboxylic acids and alcohols in the presence of an acid catalyst. Ethyl acetate is being synthesized using ethanol and acetic acid with sulfuric acid as the catalyst. Distillation reflux is used to allow continuous return of volatile materials to the flask without loss of solvent or reactants.

The acid functions as a catalyst for the esterification reaction between the carboxylic acid and alcohol. It protonates the carboxylic acid, making it a better leaving group and allowing it to be displaced by the alcohol, forming the ester product.

The temperature must be kept around 77°C during synthesis because that is the boiling point of ethyl acetate. Distilling at that temperature allows the ethyl acetate product to be separated from the reaction mixture via simple distillation.

PW of Organic chemistry

Unit 4: Synthesis of ethyl acetate (Distillation reflux)


Synthesis of ethyl acetate (Distillation reflux)

Objective :
1. Understand of preparation of esters by Fisher reaction
2. Understand and able to use distillation reflux in organic chemistry
synthesis
Synthesis of ethyl acetate (Distillation reflux)
I. Introduction
➔ Esters are produced when carboxylic acids are heated with alcohols in the
presence of an acid catalyst

➔ Ethyl acetate (EtOAc) :


- Colorless liquid has a characteristic sweet smell ( similar to
pear drops )
- Use as solvent for paints, varnishes, lacquers, cleaning
mixtures, and perfumes , decaffeinating coffee beans

➔ Distillation reflux :
- allow continuous return of the volatile materials to the flask
- no solvent or reactant is removed or lost
Synthesis of ethyl acetate (Distillation reflux)
II. Procedure
Ethyl acetate is synthesised from by heating EtOH with HAc in the presence of a
catalytic amount of a strong acid such as H2SO4
Synthesis of ethyl acetate (Distillation reflux)
II. Procedure Add Na2CO3 10% =80-100ml

Ethyl-acetate
H20
H2SO4
Acetic acid =40ml EtOH
reflux / 1 h simple distillation at 770C
EtOH =45 ml HAc
H2SO4 = 5 ml

cool to r.t
Distill until no more
liquid is yielded

Add Na2SO4
Top layer + CaCl2=20g/25ml

Ethyl acetate
B.p = 77.10C
Density = 0.902 g/ml
Synthesis of ethyl acetate (Distillation reflux)
QUESTIONS
1. What is the function of the acid in the preparation of ethyl acetate ?
(give equations)
2. Why we must kept temperature around 770c when we do synthesis ?
3. What experimental means may be used to drive an esterification towards
completion?
4. Tell how a mixture of ethyl acetate ethanol may be separated?
5. What are the role of Na2CO3 , CaCl2 and Na2SO4 ?
References
- A microscale Approach to organic laboratory techniques , Donald
th
L.Pavia,Gary M. Lampman ,5 edition
- Experimental Organic Chemistry : A Miniscale and Microscale
th
Approach, John C. Gilbert ,Stephen F.Martin ,5 edition
th
- Quantitative Chemical Analysis 7 edition , Daniel C.Harris.
- Introduction to Laboratory techniques , Pavia Kriz ,Lampman Engel ,
1998
rd
- Techniques in Organic Chemistry , 3 edition , Jerry R.Mohrig ,
Christina Noring Hammond Paul F.Schatz

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