Experiment Title:

Synthesis of benzylidene acetal

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Submitted By:

Reg No:

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Table of Contents
Synthesis of Benzylidene Acetal.................................................................................................................1
1.1 Objective:....................................................................................................................................1
1.2 Theory:.........................................................................................................................................1
1.3 Experimental Procedure:.............................................................................................................2
1.3 Results.........................................................................................................................................2
1.4 Discussions:.................................................................................................................................4
1.5 Conclusion and Recommendations:.............................................................................................4
1.6 Pre Lab Questions:.......................................................................................................................5
References:..............................................................................................................................................7

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Synthesis of Benzylidene Acetal
1.1 Objective:
 Prepare the benzylidene acetal by reacting the benzaldehyde and 1,1,1-tris ethane under
the acidic medium.
 Determine the purity of the benzylidene by using the thin layer chromatography (TLC)
and nuclear magnetic resonance (NMR)

1.2 Theory:
In organic chemistry most the reactants are reacted with each other to form a products by using
some catalyst and providing the operating conditions and it is a powerful tool to convert the
simple molecules by reacting with complex molecules. Organic chemistry also synthesis the
production of natural products that are used in food, cosmetics, medicals and textiles fields.
Plants and animals produce the natural products by consuming the large time. Organic chemistry
find some synthetic way for the production of these complex molecules. When the reaction is
takes, there is a chance of many other functional group molecules. By using the protective
groups, we can decrease the formation of byproducts and block a functional group from
undergoing chemical reaction. Protecting groups can easily be removed from the main functional
group after the completion of reaction. There are many functional groups like amines and
alcohols that needs protection in multistep to ensure that they are not converted into some
byproducts.

In this experiment, our main focus is to protect the aldehyde substrate during the formation of
acetal. Acetal is produced by reacting the hydroxyl groups with aldehyde under acidic medium.
This process involves the protonation of carbonyl group to form hemiacetal. Protonation of
hemiacetal and nucleophilic attach yield our desired product.

In organic chemistry, we prepare the benzylidene acetal by reacting the benzaldehyde with 1,1,1-
tris ethane under acidic conditions. It is a functional group with formula C 6H5CH(OR)2 and is
used as protecting groups in glycochemistry. These compounds can also be converted into the
carboxylic acids in order to produce some biological molecules like glycosaminoglycans.

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Chemical Reaction:

H2SO4

1.3 Experimental Procedure:

 Firstly rinse the round bottom vial and magnetic stir with acetone and allow them to dry.
 In vial, add 1.1g of 1,1,1 tris ethane, 2,5mL of water and 10 drops of concentrated
sulphuric acid.
 Stir the reaction for 5 minutes to dissolve all the solids in the water.
 When the solids have been dissolved, add 5.6mL solution of benzaldehyde in the reaction
mixture and stirrer it for 15 minutes vigorously.
 After 15 minutes, add some ice cubes in the reaction mixture and continue to vigorously
stir.
 When the precipitates of benzylidene acetate is formed, put the solution into ice bath for
10-15 minutes.
 Using Hirsch funnel, collect the precipitates by vacuum filtration and wash it with water
for 3 times.
 Put the crude product into the 25mL flask and add 10mL of toluene into flask and gently
heat.
 When two layers are formed in the flask, use the glass pipette to remove aqueous layer.
 Dry the solution by adding spatula tip of Na2So4 for 5 minutes. It will absorb all water
present in it.
 Add 10mL of petroleum ether into 30mL beaker to decant the solution for 5 minutes.
 Wash the product with petroleum ether for 3 times after collecting it through the Hirsch
funnel and measure the weight of product.
 Performed the thin layer chromatographic analysis of the product and find the Rv value
and find the product yield.

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1.3 Results
In this experiment, we find the product mass and product purity by using the Thin Layer
Chromatography and Nuclear magnetic resonance Spectroscopy.
Weight of product = 0.930 g

Following are the results of THL and NMR.

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1.4 Discussions:
Thin layer chromatography results shows that small amount of product is also present in the
reactants. In this section, we dissolve our product into acetone solution and put it into the
chromatography jar and analyze in the presence of UV light. UV light indicates that small
amount of reactants is also present in it which means that our product is not 100% pure. We also
did the analysis by using SMR for finding the product quality. SMR peaks shows that small
amount of concentration of impurity is present in benzylidene acetal.

1.5 Conclusion and Recommendations:

In this experiment, we make the protecting group benzylidene acetal by reacting the
benzaldehyde with 1,1,1 tris ethane in the presence of acidic medium. Sulphuric acid provides
the acidic medium for the reaction. After product formation, we did the analysis for the purity by
using NMR and SMR spectra. We can also prepare our desired product at room temperature by
using Dowex 50WX8 which is acting as a solid catalyst and Cl 3CCN as a noval water
scavenger. We can get maximum yield at room temperature because wide variety of aryl and α,β‐
unsaturated aldehydes react readily with functionalized 1,2‐ and 1,3‐diols to develop the
corresponding acetals in very good yields.

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1.6 Pre Lab Questions:

Question No.01

Acetals and ketals involve the dehydration process because in the presence of water acetals is
converted back to the hemiacetals which decrease our product yield. As we know that reaction is
reversible in nature so to keep the reaction is in equilibrium, we must remove water from it for
high productivity. In this experiment, water is used as a solvent because it neutral and can easily
absorb the reactants in which reaction is takes place in acidic medium. Acetal produced in this
reaction is in solid state and solubility of acetals

Question No.02

Question No. 03

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During filtration process , precipitates of acetal is recovered from the top of the filter while
aqueous solution which contains water, sulphuric acid and unreacted components are removed
from the bottom of the flask. After filtration, precipitates is washed by using water so it absorbs
water and during crystallization water is dehydrated from the acetals.

Question No.04

As we know that acetals are used to protect the 1,2-and 1,3-diol molecules in which acetone is
used to protect 1,2-diol and benzaldehyde is used to protect the 1,3-diol.

Reaction of 1,2-diol:

Reaction of 1,3-diol:

The theory is that the formation of the six-membered cyclic acetal is less favorable with acetone
than it is for benzaldehyde, because with acetone you cannot avoid having one methyl group
being axial. The next-most stable thing after a six-membered ring is a five-membered ring, which
can be formed by the protection of a 1,2-diol instead of a 1,3-diol.

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References:

1. Klein, D. R. (2021). Organic chemistry. Hoboken, NJ: Wiley.

2. Carey, F. A., Giuliano, R. M., Allison, N. T., & Bane, T. S. (2020). Organic chemistry.
New York, NY: McGraw-Hill Education.
3. Perkin, W. H., Kipping, F. B., & Kipping, F. S. (1941). Organic chemistry. London:
Chambers.