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OBJECTIVES:

This experiment aims to:


- Synthesize benzyl acetate through Fischer Esterification occurring through a
nucleophilic acyl substitution mechanism
- Successfully use the reflux technique to synthesize benzyl acetate
- Understand mechanism involved in the reaction
- Evaluate efficiency of Fischer Esterification as a method of synthesizing esters

INTRODUCTION:
Esters are some of the most widespread naturally-occurring compounds. Many
esters are responsible for the fragrance of flowers and fruits like bananas, raspberries,
and peaches and are also the primary constituent of fats and oils. Esters are usually
formed from acid-catalyzed condensation of a carboxylic acid and an alcohol where the
two molecules combine to form a bigger molecule. This type of reaction is called a
nucleophilic acyl substitution. Fischer Esterification is the most useful method in
synthesizing esters because of its relatively high yield. This process is done by using a
carboxylic acid and an alcohol in the presence of an acid catalyst. In this reaction, the
carboxylic acid is activated with an acid to make the acyl carbon more electrophilic. Thus,
the alcohol can attack the acyl carbon and the deprotonation of the acyl oxygen forms
the ester.

PRELAB QUESTIONS:
1. How is the yield of the reaction maximized? How is the hydrolysis of benzyl
acetate back to benzyl alcohol and acetic acid prevented? Explain.
To maximize the yield of the reaction, the reaction mixture is washed with
water to remove unreacted benzyl alcohol and excess acetic acid. A
second wash with bicarbonate is also utilized to remove any remaining
traces of acetic acid. The ester must also be removed immediately as it
forms. Another way to drive the reaction forward is to add an excess of
acetic acid because it is easier to remove after the reaction. Because
esterification is a reversible reaction, it is important to remove compounds
such as water and strong bases that aid in inducing the reverse of
esterification or hydrolysis process. These compounds are removed during
the purification stage of the crude product.
2. What is the use of the sodium bicarbonate wash? What gas is produced upon the
addition of sodium bicarbonate into the organic layer?
The sodium bicarbonate wash removes any remaining trace of acetic acid.
It is also used to neutralize any unreacted acid. Sodium bicarbonate is a
weaker acid thus its reaction with the unreacted acid catalyst will produce
carbonic acid which dissociates into water and carbon dioxide. Thus,
sodium bicarbonate must be added before removing the aqueous layer in
the last washing and before drying the organic layer. Carbon dioxide is the
gas produced.
3. What is the use of sodium chloride in the sodium chloride wash?
Sodium chloride increases the ionic strength of the aqueous layer.
Therefore, the separation of the aqueous and organic layer will be easily
observed. Sodium chloride also aids in removing polar impurities and water
from the crude ester.
4. Where would you expect the organic layer to be in each of the three washing
steps?
For the first wash with 15mL cold water, the organic layer is at the bottom
of the separatory funnel because the benzyl acetate is denser than water.
Thus, the organic layer is drained into an Erlenmeyer flask. For the second
and third wash, the organic layer is at the top of the separatory funnel
because sodium bicarbonate and sodium chloride both have higher
densities than benzyl acetate. Therefore, they sit at the bottom of the
funnel and are drained through the stopcock.
5. What are the qualitative tests to verify the presence of benzyl acetate and benzyl
alcohol? What constitutes a positive test result?
The Hydroxamic Acid test can help verify the presence of an ester in the
benzyl acetate product. A positive result is seen if the test produces a red-
violet solution. Meanwhile, a Chromic Acid test is used to check for the
presence of an alcohol. A positive result is indicated by the presence of
blue-green precipitate. If the Chromic Acid test results in a positive test
result, then the benzyl acetate product still contains traces of benzyl
alcohol and was not fully synthesized.
REAGENTS:
PHYSICAL AND CHEMICAL
REAGENTS SAFETY PRECAUTIONS
PROPERTIES
Benzyl Acetate (IUPAC) Molecular Weight: 150.18 g/mol Skin and eye irritant: flush with
[C9H10O2] Boiling Point: 213oC water for at least 15 mins. then get
Melting Point: -51oC medical assistance
Density: 1.05 g/cm3 Ingestion (hazardous): do not
Solubility: 3.1 mg/mL (25oC) in induce vomiting unless instructed
water by medical personnel
Appearance: Colorless liquid with Inhalation (hazardous): to fresh
pear-like odor, bitter-pungent taste air, give oxygen, seek medical
assistance
Combustible
Acetic Acid (IUPAC) [C2H4O2] Molecular Weight: 60.052 g/mol Skin and eye irritant: flush with
Boiling Point: 117.9oC water if contact
Melting Point: 16.6oC Serious skin contact: Wash with
Density: 1.05 g/cm3 disinfectant soap and cover
Appearance: Colorless liquid or contaminated skin with anti-
crystals with a sour, vinegar-like bacterial cream. Seek medical aid
odor Ingestion (hazardous): do not
induce vomiting unless instructed
by medical personnel
Inhalation (hazardous): remove to
fresh air, give oxygen, seek
medical assistance
Sodium Bicarbonate / Sodium Molecular Weight: 84.007 g/mol Skin and eye irritant: flush with
hydrogen carbonate (IUPAC) Boiling Point: 851oC water if contact
[NaHCO3] Melting Point: 50oC Ingestion: do not induce vomiting
Density: 2.1 g/cm3 unless instructed by medical
Solubility: 8.7 g/100mL (20oC) of personnel
water Inhalation: remove to fresh air,
Appearance: White crystalline give oxygen, seek medical
powder or granules, odorless, assistance
saline and slightly alkaline taste
Sodium Chloride (IUPAC) [ClNa] Molecular Weight: 58.44 g/mol Skin and eye irritant: flush with
Boiling Point: 1465oC water if contact
Melting Point: 800.7oC Serious skin contact: Wash with
Density: 2.17 g/cm3 disinfectant soap and cover
Solubility: 36.0 g/100g (25oC) of contaminated skin with anti-
water bacterial cream. Seek medical aid
Appearance: Colorless to white Ingestion: do not induce vomiting
crystalline solid, salty taste unless instructed by medical
personnel
Inhalation: remove to fresh air,
give oxygen, seek medical
assistance
Sulfuric Acid (IUPAC) [H2SO4] Molecular Weight: 98.079 g/mol Skin and eye irritant (very
Boiling Point: 337oC hazardous): flush with water if
Melting Point: 10.31oC contact
Density: 1.84 g/cm3 Serious skin contact: Wash with
Solubility: miscible (20oC) in disinfectant soap and cover
water contaminated skin with anti-
Appearance: Odorless colorless bacterial cream. Seek medical aid
oily hygroscopic liquid Ingestion (very hazardous): do not
induce vomiting unless instructed
by medical personnel
Inhalation (very hazardous):
remove to fresh air, give oxygen,
seek medical assistance

REFERENCES:
- GuidoteAM,delRosarioDR,AbuzoAL.ExperiencingOrganicChemistry.QuezonCity:OfficeofResearchand
Publications,AteneodeManilaUniversity;2005.
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2005March25[updated2017March26;cited2017March26].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/benzyl_acetate
- [AuthorUnknown].Sciencelab.com[Internet].USA:Sciencelab.com,Inc.;unknownfirstpublication[cited2017
March26].Availablefrom:http://www.sciencelab.com/msds.php?msdsId=9923066
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2004September16[updated2017March25;cited2017March26].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/acetic_acid
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March19].Availablefrom:http://www.sciencelab.com/msds.php?msdsId=9922769
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2005March27[updated2017March25;cited2017March26].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_bicarbonate
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March26].Availablefrom:http://www.sciencelab.com/msds.php?msdsId=9927258
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2005March25[updated2017March25;cited2017March26].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_chloride
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https://pubchem.ncbi.nlm.nih.gov/compound/sulfuric_acid
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https://www.scribd.com/doc/295968779/SYNTHESISOFBENZYLACETATETHROUGHFISCHER
ESTERIFICATIONREACTION
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PROCEDURES:

Pour 5.5mL of acetic acid and 3-5 drops


(~0.2mL) of concentrated sulfuric acid into RBF.
Slowly add 4.5mL of benzyl alcohol into mixture
and swirl it.

Secure setup with clamps on neck of


Attach water condenser vertically over mouth of
RBF and on body of condenser
round bottom flask. Check setup for leaks and
heat RBF to slow boil. Continue heating RBF Regulate heat in order to prevent
over low-medium heat for an hour.. formation of solid byproducts

Let mixture in RBF cool down and decant into


separatory funnel. Wash RBF with 15mL cold
water and use to wash mixture in separatory fun

Drain organic layer into clean and dry The order of the organic and aqueous layers
Erlenmeyer flask and discard aqueous layer. in separatory funnel changes throughout
Wash organic layer with 10mL 5% NaHCO3 and experiment due to changing density of
then with 10mL 10% NaCl. aqueous layer
Make sure layers are properly identified

Decant organic layer into Erlenmeyer flask and


dry over sodium sulfate. Distill it if necessary and
store in scintillating vial. Perform qualitative
tests.