Name: BAUTISTA, John Mhar M.

Date submitted: June 14, 2022

Couse and Section: BSCRIM 2-A

Experiment No. 7

ESTERS

Introduction:

Ester is a carbonyl with an alkyl or aryl group (R) on one side, and an oxygen bound to another
alkyl or aryl group (R’) on the other side, represented by the general formula: RCOOR’. Esters
can be commonly derived by an esterification reaction between a carboxylic acid and an alcohol.
The hydroxyl group of the carboxylic acid is replaced by an alkyl or aryl group. Simple esters,
which have low molecular weight and small R and R’ functional groups, have smells and flavors
of fruits and flowers.
The simplest carboxylic acid is formic acid (HCOOH), with the simplest alcohol being methanol.
Thus, the simplest ester formed from the esterification of these two molecules is methyl formate
(HCOOCH3). Methyl formate is considered a derivative of formic acid because the OH group is
replaced by the OCH3 group. The structural differences between methyl formate and formic acid
dictate the difference in their properties. This is because the properties of the molecule depend
heavily on the R and R’ groups.
Esters that are found in fruits and flowers are known as simple esters due to the low complexity
of their structure in comparison to other esters. The alkyl and aryl groups found on these esters
greatly influences the fragrance they emit; thus, the addition of a carbon or a different functional
group can impact the scent produced by the ester. For example, propyl acetate (C5H10O2) has the
scent of pears. However, butyl acetate (C6H12O2), which has only one more carbon in its chain,
smells like apples.
Esters are usually formed by a condensation reaction between alcohol (R’-OH) and carboxylic
acid (R-COOH), and the reaction is known as esterification. Condensation reactions are
characterized by the linking of two reactants to form a larger product (in terms of the number of
molecules) and the removal of a smaller molecule. In esterification reactions, water (H2O) is the
smaller molecule that gets eliminated.
R’OH + RCOOH ⇌ RCOOR′ + H2O
However, organic alcohol and carboxylic acids do not react readily, and when they do, the
reaction is highly reversible. Therefore, an acid catalyst, such as sulfuric acid, is generally added
to the reactant mixture (Fischer esterification).
The catalyst serves two purposes—speeding up the reaction (like any other catalyst) and acting
as a dehydrating agent. Sulfuric acid consumes the eliminated water molecule and prevents the
hydrolysis of the newly formed ester. This forces the reaction equilibrium to the right and results
in a greater product yield. Additionally, esterification is carried out at temperatures near the
boiling point of the reacting alcohol to boost reaction rate.
Esterification isn’t the only method used to produce esters. Esters can also be produced by
merging two carboxylic acid molecules via treatment with diazomethane or epoxides,
reacting acyl chlorides (RCOCl) or acid anhydrides (R(CO)O(CO)R’) with alcohols, or alkenes
(CnH2n) with metal carbonyls, etc. An ester can also be derived from another ester using the
process of transesterification.

For the step by step procedure, watch:

https://www.youtube.com/watch?v=V6HVI7F6C8Q

Experimental Data:

TEST NAME OF NAME OF DESCRIPTION EVIDENCE NAME OF

TUBE CARBOXYLIC ALCOHOL OF SMELL OF OILY ESTER
NO. ACID USED USED DROPLETS? FORMED
(YES OR NO)
1 Ethanoic Acid Methanol Glue, Chemical No Methyl
Ethanoate

2 Propanoic Acid Ethanol Pineapple, Sweet No Ethyl

Propanoate
3 Butanoic Acid Propan-1-ol Pear, Sweet Yes Propyl
Butanoate
 4 Methanoic Acid Butan-1-ol Raspberry, Sweet Yes Butyl
Methanoate

QUESTIONS:
1. What is ester used for?
The main use of esters is for flavorings and perfumes; however, they can also be used in
the chemicals industry as solvents. Esters are formed in condensation reactions and broken by
hydrolysis. Fats and oils, important compounds in our diet, are naturally occurring esters and their
structure explains their properties.
Esters are formed by the condensation reaction between an alcohol and a carboxylic acid.
This is known as esterification. In a condensation reaction, two molecules join and produce a larger
molecule whilst eliminating a small molecule. During esterification this small molecule is water.
Esters have characteristic smells and are insoluble in water.
Certain volatile esters are used as solvents for lacquers, paints, and varnishes; for this
purpose, large quantities of ethyl acetate and butyl acetate are commercially
produced. Waxes secreted by animals and plants are esters formed from long-chain carboxylic
acids and long-chain alcohols. Fats and oils are esters of long-chain carboxylic acids and glycerol.

2. In the experiment, what is the function of H2SO4?

In esterification reactions, concentrated H2SO4 (sulfuric acid) is known to be used as a
catalyst. Here, the sulfuric acid plays a dual role – it works to speed up the rate of the reaction
while simultaneously acting as a dehydrating agent, thereby forcing the equilibrium reaction to the
right. This results in a greater yield of the required ester.

Esterification is a relatively slow process at room temperature and does not proceed to completion.
Concentrated sulfuric acid is used as a catalyst which speeds up the reaction and also acts as a dehydrating
agent, forcing the equilibrium to the right and resulting in a greater yield of ester.

3. Why do esters smell?

Esters smell partly because they exhibit weak intermolecular forces. This allows ester
molecules to enter the gas phase and reach your nose. Esters don't exhibit intermolecular hydrogen
bonding, unlike alcohols, for example. These are no strongly positively polarized hydrogens in
esters to participate in hydrogen bonding. Consider for example ethyl butyrate, which smells like
pineapples.
The odors of esters are distinctly different from those of the corresponding acids. Acids
have unpleasant smells, but esters have fruity smells. In fact, esters are responsible for the odors
of many fruits. For example, ethyl ethanoate occurs in pineapples, 3-methylbutyl ethanoate in
apples and bananas, 3-methylbutyl-3-methylbutanoate in apples, and octyl ethanoate in oranges.
 4. What are the physical and chemical properties of esters?

Physical Properties of Ester

• Esters are colorless, pleasant smelling liquids, while those of higher acids are colorless solids.
• Lower esters are fairly soluble in water. The solubility of esters in water decreases rapidly with increase
in the mass.
• The boiling points of methyl and ethyl esters are lower than those of the corresponding parent acids.

Chemical Properties of Ester

• Esters are less reactive than acyl chlorides and acid anhydrides.
• Esters slowly react with ammonia to form amides and alcohols.
• Esters undergo hydrolysis slowly to form the parent carboxylic acid and alcohol.
• LiAlH4 reduces esters into primary alcohols.

5. What other class of compounds can be reacted with alcohols to give esters?
Making esters from alcohols and acyl chlorides. Esters can also be made from the reactions
between alcohols and either acyl chlorides (acid chlorides) or acid anhydrides.If you add an acyl
chloride to an alcohol, you get a vigorous (even violent) reaction at room temperature producing
an ester and clouds of steamy acidic fumes of hydrogen chloride. For example, if you add the
liquid ethanoyl chloride to ethanol, you get a burst of hydrogen chloride produced together with
the liquid ester ethyl ethanoate.
Making esters from alcohols and acid anhydrides. The reactions of acid anhydrides are
slower than the corresponding reactions with acyl chlorides, and you usually need to warm the
mixture. Taking ethanol reacting with ethanoic anhydride as a typical reaction involving an
alcohol. There is a slow reaction at room temperature (or faster on warming). There is no visible
change in the colorless liquids, but a mixture of ethyl ethanoate and ethanoic acid is formed.