Ester Synthesis Lab (Student Handout) PDF

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Ester Synthesis Lab (Student Handout)

Esters are produced by the reaction between alcohols and carboxylic acids. For example reacting ethanol with acetic acid to give ethyl acetate is shown below.

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Esters can beprepared bythis method in the presence of an acid catalyst To force the reactionequilibriumtotheright(infavoroftheester)oneofthestartingmaterialsmustbeusedinexcess As the carboxylic acid ismore easily removed from the reaction mixtureit will be used as theexcess reagent

How are esters prepared?

Esters are readily prepared from the condensation reaction of a carboxylic acid and an alcohol, catalyzed by the addition of a strong acid such as sulfuric acid. This reaction is described as: The reactions illustrate how the names of esters are derived.

What does an ester smell like?

TERM 1: PRACTICAL WORK KNOWLEDGE AREA: MATTER AND MATERIALS 5.1 PREPARATION OF ESTERS AND SMELL IDENTIFICATION INTRODUCTION Esters have a very fruity smell. Naturally occurring esters are found in fruits. Esters can be synthesised by the reaction of a carboxylic acid and an alcohol. This reaction is known as esterification.

How do carboxylic acids and alcohols make esters?

In this lab, several different carboxylic acids and alcohols will be used to make several esters. Esters are readily prepared from the condensation reaction of a carboxylic acid and an alcohol, catalyzed by the addition of a strong acid such as sulfuric acid. This reaction is described as:

What chemicals are in a Grade 12 Chemistry exam?

• Chemicals: methanol, ethanol, propanol, ethanoic acid, salicylic acid, sulphuric acid and 0,5 mol.dm-3sodium carbonate PHYSICAL SCIENCES SCHOOL-BASED ASSESSMENT EXEMPLARS – 7 CAPS GRADE 12 TEACHER GUIDE

Name: ________________________

Lab Partner: __________________

_ _

Date: ________________________

_ _

Class Period: __________________

_ _

Ester Synthesis Lab (Student Handout)

Lab Report

Components:

The following must be included in your lab book in order to receive full credit. 1.

Purpose

Hypothesis

Procedure

Observation/Data Table

Results

Mechanism (In class)

Conclusion

Introduction

The compounds you will be making are also naturally occurring compounds; the chemical structure of these compounds is already known from other investigations.

Esters are organic molecules of the general form:

where R1 and R 2 are any carbon chain. Esters are unique in that they often have strong, pleasant odors. As such, they are often used in fragrances, and many artificial flavorings are in fact esters. Esters are produced by the reaction between alcohols and carboxylic a cids. For example, reacting ethanol with acetic acid to give ethyl acetate is shown below.

In the case of ethyl acetate, R

1 is a CH 3 group and R2 is a CH 3 CH 2 group. Naming esters systematically requires naming the functional groups on both sides of the bridging oxygen. In the example above, the right side of the ester as shown is a CH 3CH 2 2 group, or ethyl group. The left side is CH 3

C=O, or acetate. The name of the ester is

therefore ethyl acetate. Deriving the names of the side from the carboxylic acid merely requires replacing the suffix ic with ate.

Materials

Alcohol

o 1 o 2 o 3 o

4 Carboxylic Acid

o A o B o C

Observation Parameters:

Record the combination of carboxylic acid and alcohol

Observe each reactant

Observe each product

Procedure

Construct a data table that lists each ester to be synthesized, along with the alcohol and carboxylic acid you will use in the synthesis reaction. Provide space to note observations about the properties of each reactant and product. Your

teacher will review and approve your data table before you begin. a. You will make a total of three combinations!! 2. Before you begin, put on your goggles, and wear them properly throughout the investigation. 3. Prepare a hot-water bath by adding ~50 mL tap water to a 100-mL beaker. Place the beaker on a hot plate, and heat the water until it is near boiling (60-70C). Be sure that no flames or sparks are in the area. (Note: Use a hot plate, not a Bunsen burner, to heat the water bath.) 4. Obtain a small, clean test tube. Place 20 drops of the appropriate alcohol into the tube. Next add 0.1 g or 60 drops of the carboxylic acid (as identified in your table). Then add 2 drops of concentrated sulfuric acid to the tube. a. Caution: Concentrated sulfuric acid is corrosive and will cause burns to skin or fabric. Add the acid slowly and very carefully. If any sulfuric acid accidentally spills on you, ask a classmate to notify your teacher immediately. Wash the affected area immediately with tap wate r and continue rinsing for several minutes. Other than water and sulfuric acid, the substances used in this investigation are volatile and flammable. 5. As you dispense these compounds, record any observations you notice. 6. Place the test tube in the hot-water bath you prepared using a test tube clamp. 3 7. Keep the tube in the hot water, and do not spill the contents. 8.

Continue heating for five minutes.

9. While this is heating, fill an Erlenmeyer flask about 1/3 way full with water. 10. Once heating is finished, carefully add the combination of the acid and alcohol to the flask. 11. Repeat Steps 3 through 7 using 20 drops of alcohol and 60 drops or 0.1 g (depending upon physical state) of carboxylic acid, along with 2 drops of concentrated sulfuric acid for each of the esters in your table. (Caution: Avoid inhaling any test tube C fumes) 12. Dispose of your products as directed by your teacher. 13. Wash your hands thoroughly before leaving the laboratory.

Observation/Results

*Make a detailed data table to record the combination of carboxylic acid and alcohols an the observations that go along with that.

Results/Mechanism

1. Write the chemical reactions for each of the esters produced in the above procedures.

Conclusion

1. Octanol, methanol, propanol and n-butanol contain what functional group of all alcohols? 2. Acetic acid and salicylic acid contain what functional group characteristic of all carboxylic acids? 3.

The esters produced in this laboratory experiment contain what functional group characteristic of all ester?

4. Isobutyl alcohol and formic acid combine to produce a raspberry odor. Predict the name of the ester. 4

Teacher Information

Here are the mixtures and labels

Carboxylic Acid Alcohol Ester Scent

Salicylic Acid (A) Methanol (1) Methyl salicylate Wintergreen Propanoic Acid (B) Methanol (1) Methyl propionate Rum Ethanoic acid (C) Butan-1-ol (2) Butyl Ethanoate Banana Ethanoic Acid (C) Octan-1-ol (3) Octyl Ethanoate Orange Ethanoic acid (C) Propan-1-ol (4) Propyl Ethanoate Pear

In this investigation,

students will synthesize esters. The esters produced have very familiar and pleasing fragrances. Many perfumes and artificial flavorings contain esters. In fact, the characteristic aromas of many herbs and fruits arise from esters found naturally in those plants.

The compounds you

r students will be making are also naturally occurring compounds; the chemical structure of these compounds is already known from other investigations. Note how the functional groups of the acid and alcohol combine to form a water molecule, while the remaining atoms join to form an ester molecule. Construct a data table that lists each ester to be synthesized, along with the alcohol and carboxylic acid you will use in the synthesis reaction. Provide space to n ote observations about the properties of each reactant and product.

ANSWERS

Results/Mechanism

1. Write the chemical reactions for each of the esters produced in the above procedures.

Reaction # Carboxylic Acid Alcohol Ester Scent

1 Salicylic Acid (A) Methanol (1) Methyl salicylate Wintergreen

2 Propanoic Acid (B) Methanol (1) Methyl propionate Rum

3 Ethanoic acid (C) Butan-1-ol (2) Butyl Ethanoate Banana

4 Ethanoic Acid (C) Octan-1-ol (3) Octyl Ethanoate Orange

5 Ethanoic acid (C) Propan-1-ol (4) Propyl Ethanoate pear

Reaction 1:

+ + H 2 O methanol salicylic acid methyl salicylate 5

Reaction

2 + + H 2 O methanol propanoic acid

Methyl propionate

Reaction

3 + + H 2 O butan -1-ol ethanoic (acetic) acid Butyl Ethanoate

Reaction

4 + + H 2 O octanol ethanoic (acetic) acid

Octyl Ethanoate

Reaction

5 + + H 2 O propanol ethanoic (acetic) acid

Propyl Ethanoate

Conclusion

2.quotesdbs_dbs4.pdfusesText_8

[PDF] Ester Synthesis Lab (Student Handout)

How are esters prepared?

What does an ester smell like?

How do carboxylic acids and alcohols make esters?

What chemicals are in a Grade 12 Chemistry exam?

Name: ________________________

Lab Partner: __________________

Date: ________________________

Class Period: __________________

Ester Synthesis Lab (Student Handout)

Lab Report

Components:

Purpose

Hypothesis

Procedure

Observation/Data Table

Results

Mechanism (In class)

Conclusion

Introduction

Esters are organic molecules of the general form:

In the case of ethyl acetate, R

C=O, or acetate. The name of the ester is

Materials

Alcohol

4 Carboxylic Acid

Observation Parameters:

Observe each reactant

Observe each product

Procedure

Continue heating for five minutes.

Observation/Results

Results/Mechanism

1. Write the chemical reactions for each of the esters produced in the above procedures.

Conclusion

Teacher Information

Here are the mixtures and labels

Carboxylic Acid Alcohol Ester Scent

In this investigation,

The compounds you

ANSWERS

Results/Mechanism

1. Write the chemical reactions for each of the esters produced in the above procedures.

Reaction # Carboxylic Acid Alcohol Ester Scent

1 Salicylic Acid (A) Methanol (1) Methyl salicylate Wintergreen

2 Propanoic Acid (B) Methanol (1) Methyl propionate Rum

3 Ethanoic acid (C) Butan-1-ol (2) Butyl Ethanoate Banana

4 Ethanoic Acid (C) Octan-1-ol (3) Octyl Ethanoate Orange

5 Ethanoic acid (C) Propan-1-ol (4) Propyl Ethanoate pear

Reaction 1:

Reaction

Methyl propionate

Reaction

Reaction

Octyl Ethanoate

Reaction

Propyl Ethanoate

Conclusion