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