chApTer 1 investigations

investigation
i 1.4.1 conTrolled eXperiMenT SKIllS MENu

• Questioning • Planning • Analyzing

Properties of Alcohols • Researching
• Hypothesizing
• Controlling Variables
• Performing
• Evaluating
• Communicating
• Predicting • Observing
Chemical properties within a group of alcohols may follow
WHIMIS Flammable.ai
a trend. In this investigation, you will use your knowledge
of intermolecular forces and the structure of alcohol Alcohols and cyclohexane are flammable. They should be
molecules to predict trends in the properties of alcohols. used only in a well-ventilated area. There should be no open
You will test one of your predictions experimentally. flames or other sources of ignition in the laboratory.

Testable Question Procedure SKILLS

HANDBOOK A1, A2.2, A3.3

What is the trend in melting points, boiling points, and 1. Read through the MSDS and list the hazards of the
solubility of the primary alcohols butan-1-ol, propan-1-ol, chemicals you will be using. Include this information,
and ethanol? and how to minimize the hazards, in your report.
2. Put on your safety goggles and apron.
Hypothesis 3. Use the wax pencil to label the 3 test tubes. Using the
Use your understanding of the structures of alcohols to pipette, place about 1 mL of ethanol in one test tube,
predict the trend of the melting points, boiling points, 1 mL of propan-1-ol in the second test tube, and
and solubility of primary alcohols. Give reasons for your 1 mL of butan-1-ol in the third test tube.
predictions. 4. To each test tube, add 1 mL of cyclohexane. Record
your observations.
variables 5. Follow your teacher’s instructions for the disposal of
Identify all the major variables that will be measured the liquids and for cleaning the test tubes.
and/or controlled in this experiment. Also identify the
6. Set up the test tubes as described in Step 3. Follow
independent variable and the dependent variable.
Step 4 but use distilled water in place of cyclohexane.
Experimental design observations
Use reference sources to determine the melting points Prepare a table in which to record your observations. In
and boiling points of three alcohols. Th
e solubility of each addition, record the melting point and boiling point data. C

alcohol is determined by mixing the alcohol with a non-

polar solvent, cyclohexane, and with a polar solvent, water. Analyze and Evaluate
(a) What variables were measured/recorded and/or
Equipment and Materials
manipulated in this investigation? What type of
• chemical safety goggles relationship was being tested? T/I
• lab apron
(b) Did the evidence that you collected allow you to
• MSDS for each chemical used answer the testable question? If so, answer the
• 3 test tubes question. If not, explain why not. T/I
• test-tube rack
(c) Compare your answer in (b) to your hypothesis. Did
• wax pencil the evidence support your hypothesis? Explain. T/I
• 3 mL calibrated disposable pipette (or similar
(d) Evaluate your hypothesis. T/I
pipetting device)
WHIMIS Flammable SM.ai
• small stoppered bottles containing
WHIMIS Flammable SM.ai Apply and Extend
- butan-1-ol
WHIMIS Flammable SM.ai
(e) Predict, in a qualitative way, the melting points,
- ethanol
WHIMIS Flammable SM.ai boiling points, and solubilities of larger primary
- propan-1-ol alcohols. Include an explanation for your prediction,
- cyclohexane referring to the forces of attraction between
• wash bottle containing distilled water molecules. T/I

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 Investigation 1.5.1 OBSERVATIONAL STUDY SKILLS MENU

• Questioning • Planning • Analyzing

Reactions of Three Isomers • Researching
• Hypothesizing
• Controlling Variables
• Performing
• Evaluating
• Communicating
of Butanol • Predicting • Observing

Alcohols that have different structures form different

Procedure SKILLS
HANDBOOK A1, A2.3, A5.1
products. The location of the hydroxyl bond is particularly
important. In this investigation, isomers of butanol are 1. Put on your safety goggles, apron, and protective gloves.
used as examples of primary (1°), secondary (2°), and 2. Put 3 test tubes in a test-tube rack. From the dropper
tertiary (3°) alcohols. You will examine the relationship bottles, place 2 drops of butan-1-ol in the first test tube,
between structure and product formed. 2 drops of butan-2-ol in the second test tube, and 2
First, you will mix each of the three isomers of butanol drops of 2-methylpropan-2-ol in the third test tube.
with concentrated hydrochloric acid. The presence of 3. Under the fume hood, your teacher will add 10 drops
an alkyl halide will be indicated by the cloudiness of the of concentrated hydrochloric acid to each of your 3 test
mixture because alkyl halides are only slightly soluble in tubes. Gently shake the mixtures very carefully. Return
water. to your lab bench with the test-tube rack and test
Next, you will mix each alcohol with dilute potassium tubes. Allow the tubes to stand for 1 min and observe
permanganate solution. This provides the conditions for for evidence of cloudiness. Record your observations.
controlled oxidation. Any colour change of the potassium
4. Follow your teacher’s instructions for the disposal of the
permanganate solution is an indication that an oxidation
contents of the test tubes and for cleaning the test tubes.
reaction has taken place.
5. Set up the 3 test tubes again, as described in the setup
Purpose part of Step 2. This time, use 4 drops of each alcohol.
To test the reactions of primary, secondary, and tertiary 6. To each test tube, carefully add about 20 drops of
alcohols with acid and with an oxidizing agent potassium permanganate solution. Shake the mixture
carefully.
Equipment and Materials 7. Allow the tubes to stand for 5 min with occasional
•
chemical safety goggles gentle shaking. Observe and record the colour of the
•
lab apron solution in each tube.
•
protective gloves
•
3 test tubes Analyze and Evaluate
•
test-tube rack (a) What evidence of reactions did you observe? T/I
•
eyedropper
WHIMIS Flammable SM.ai (b) Write structural formula equations to represent
•
dropper bottles
WHIMIS containing
Flammable SM.ai each of the reactions that occurred. If there was no
– butan-1-ol WHIMIS Flammable SM.ai reaction, write NR. T/I C
– butan-2-ol (c) Does the evidence collected allow you to achieve the
– 2-methylpropan-2-ol
WHIMIS Corrosive SM.ai Purpose? Explain. T/I
– potassium permanganate solution, KMnO4(aq) (d) Summarize in a few sentences the halogenation and
(0.01 mol/L) WHIMIS Corrosive SM.ai controlled oxidation reactions of primary, secondary,
– concentrated hydrochloric acid, HCl(aq) (12 mol/L) and tertiary alcohols. T/I
(for teacher use only)
WHIMIS Flammable.ai
Apply and Extend
Alcohols are fl ammable. They should be used only in a well- (e) Research to find an application for at least two of the
ventilated area. There should be no open fl ames or other reactions that you observed. How does this reaction
WHIMIS Corrosive.ai
sources of ignition in the laboratory. benefit society? Does it have any drawbacks? Combine
Concentrated hydrochloric acid is very corrosive. It should only your findings with those of four or five classmates and
be handled by the teacher in a fume hood or fume cupboard. create a graphic organizer summarizing your findings.
Potassium permanganate solution is corrosive and may stain T/I C A

the skin. If you spill potassium permanganate on your skin,

WEB LINK
wash the affected area with lots of cool water and inform your
teacher.

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 Investigation 1.6.1 CONTROLLED EXPERIMENT
Properties of Carboxylic Acids
Carboxylic acids are characterized by the presence of a
carboxyl group. The physical properties and reactivity
of a carboxylic acid depend on the combination of its
polar functional group and its non-polar hydrocarbon
tail. In this investigation, you will compare the melting
point, boiling point, solubility, acidity, and reaction withWHIMIS Corrosive.ai
sodium hydrogen carbonate solution, NaHCO3(aq), of two
carboxylic acids. The acids you will investigate are ethanoic
acid and octadecanoic acid.
Testable Question
Do the chemical and physical properties such as the
melting and boiling points, solubility, acidity, and reaction
with sodium hydrogen carbonate depend on the molecular
mass of the carboxylic acid?
Hypothesis
Predict the trend you expect to observe in the melting
points, boiling points, solubility, acidity, and reaction with
sodium hydrogen carbonate as the mass of the carboxylic
acid increases. Give reasons for your prediction.
Variables
Identify all the major variables that will be measured
and/or controlled in this experiment. Also, identify the
independent variable and the dependent variable(s).
Experimental Design
The melting points of ethanoic acid and octadecanoic
acid are obtained from reference resources. The solubility
of each carboxylic acid is determined by mixing it first
with water and then with vegetable oil. The reactivity of
the acids is assessed by combining each acid with sodium
hydrogen carbonate.
Equipment and Materials
• chemical safety goggles
• lab apron
• MSDS for the chemicals used
• 10 mL graduated cylinder
• 2 test tubes
• test-tube holder
• test-tube rack
• test-tube brush
• pH meter or universal indicator paper
• wash bottle containing distilled water
• vegetable oil in a beaker
• dropper bottles containingWHIMIS Corrosive SM.ai
- concentrated ethanoic acid (glacial acetic acid)
(for teacher use only)
NEL
7924_Chem_CH01.indd 65
SKILLS MENU
• Questioning • Planning • Analyzing
• Researching
• Hypothesizing
• Controlling Variables
• Performing
• Evaluating
• Communicating
• Predicting • Observing
- dilute ethanoic acid (vinegar)
- sodium hydrogen carbonate solution, NaHCO3(aq)
(saturated)
• octadecanoic
acid (stearic acid, solid)
Concentrated ethanoic acid (glacial acetic acid) is very
corrosive. It should only be handled by the teacher in a
fume hood or fume cupboard.
SKILLS
Procedure HANDBOOK A1, A2.2, A2.5
1. Read through the MSDS and list the hazards of the
chemicals you will be using. Include this information,
and what you should do to minimize the hazards, in
your report.
2. Put on your safety goggles and lab apron.
3. Add 5 mL of water to one test tube and the same
volume of oil to a second test tube. In the fume hood,
your teacher will add one drop of glacial acetic acid
to each tube. Gently shake each tube to mix. Record
your observations on the solubility of concentrated
ethanoic acid in each solvent.
4. Still working in the fume hood, use the pH meter or
the universal indicator paper to determine the pH of
each mixture. Record your observations.
5. Follow your teacher’s instructions to dispose of the
contents of each test tube and clean the test tubes.
6. Repeat Steps 3, 4, and 5, using a small quantity of solid
octadecanoic acid (enough to cover the tip of a toothpick)
in place of the concentrated ethanoic acid. You do not
need to work in the fume hood from this step on.
7. Place 20 drops of sodium hydrogen carbonate
solution from a dropper bottle into each of the 2 clean
test tubes. Add 20 drops of dilute ethanoic acid to one
test tube and a pea-sized piece of solid octadecanoic
acid to the second test tube. Gently shake the test
tubes to mix their contents. Watch for the formation
of bubbles. Record all observations.
Observations
Prepare a table in which to record the observations made
for each test. In addition, the data table needs a space for
the melting point and boiling point data.
Analyze and Evaluate
(a) What variables were measured/recorded and/or
manipulated in this investigation? What type of
relationship was being tested? T/I
Chapter 1 Investigations 65
5/16/12 5:21 PM
 (b) Compare the solubilities of octadecanoic acid and
ethanoic acid in vegetable oil and in water. Explain
any differences in solubility. T/I
(c) Which acid, ethanoic or octadecanoic, seems to
exhibit more acidic properties? Explain. T/I
(d) Answer the Testable Question using the evidence that
you collected. T/I
(e) Compare your answer to (d) with your Prediction.
Explain any differences. T/I A
(f) Did your previous knowledge about carboxylic acids
allow you to correctly predict the chemical properties
of these acids? Provide reasons. T/I C
Apply and Extend
(g) Write a balanced chemical equation for the reaction of
ethanoic acid and sodium hydrogen carbonate. K/U
(h) Using what you discovered about trends in the
properties of carboxylic acids, predict how methanoic
acid and a carboxylic acid with 16 carbon atoms would
compare to ethanoic acid and stearic acid. T/I A
(i) Why is decanoic acid effective at hardening soaps
made with vegetable oil? Research your answer. Write
an explanation for a website designed for people who
create handmade soaps. Include a diagram with your
explanation. T/I A

WEB LINK

Investigation 1.6.2 OBSERVATIONAL STUDY SKILLS MENU

• Questioning • Planning • Analyzing

Synthesizing Esters • Researching
• Hypothesizing
• Controlling Variables
• Performing
• Evaluating
• Communicating
• Predicting • Observing
Many esters are found in fruits. Esters typically have very WHIMIS Corrosive.ai
pleasant odours. In the lab, esters can be synthesized from the
The acids are corrosive and fl ammable. Avoid skin and eye
condensation reaction between alcohols and carboxylic acids.
contact. If you spill these chemicals on your skin, wash the
affected area with a lot of cool water.
Purpose
To produce several esters and observe their odours Use caution around the hot plate. Avoid touching the heating
surface with your hands. To unplug the hot plate, pull on the
Equipment and Materials plug itself rather than the cord.
Icon_CautionHand.ai
•
chemical safety goggles Procedure
SKILLS
HANDBOOK A1, A2.3

•
lab apron
1. Put on your safety goggles and lab apron.
•
500 mL beaker
•
utility stand and ring clamp 2. Read through the MSDS and list the hazards of the
chemicals you will be using. Include this information,
•
hot plate
and what you should do to minimize the hazards, in
•
wax pencil your report.
•
3 test tubes
Icon_CautionHand Small.ai 3. Prepare a water bath by filling a 500 mL beaker half-
•
3 test-tube holders full with tap water. Dry the outside of the beaker
•
test-tube rack and place it inside the ring that is secured to a utility
•
Petri
WHIMISdishFlammable SM.ai stand so that the beaker rests on the hot plate. Heat
•
dropper bottles containing
WHIMIS Flammable SM.ai the water until it comes to a boil. Turn the heat off
– ethanol
WHIMIS Flammable SM.ai when the water starts to boil.
– propan-2-ol 4. Using the wax pencil, number the 3 test tubes in a
– pentan-1-ol WHIMISWHIMIS
Flammable SM.ai SM.ai test-tube rack. Add 10 drops of ethanol to the first test
Corrosive
– concentrated ethanoic acid (glacial acetic acid), tube, 10 drops of propan-2-ol to the second test tube,
CH3COOH(l) (for teacher use only) and 10 drops of pentan-1-ol to the third test tube.
– 2 mL concentrated sulfuric acid, H2SO4(aq) 5. Under the fume hood, your teacher will carefully add
(for teacher use only) 10 drops of concentrated ethanoic acid and 5 drops of
• wash bottle containing cold tap water concentrated sulfuric acid to each of your 3 test tubes.
WHIMIS Flammable.ai
Gently shake each test tube to mix.
Alcohols are fl ammable. They should be used only in a well-
ventilated area. There should be no open fl ames or other
sources of ignition in the laboratory.

66 Chapter 1 • Organic Compounds NEL

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 6. Return to your lab bench with the test tubes and carefully
place them in the hot-water bath. Make certain that the
test tubes do not point at anyone. Leave the test tubes in
the hot-water bath for 5 min and then, using a test-tube
holder, move the test tubes back to the test-tube rack.
7. Pour the contents of the first test tube into a Petri dish
half-filled with cold water (approximately 10–20 mL).
Smell the odour of the ester as instructed by your teacher.
Figure 1 illustrates proper technique for identifying the
odour of the ester. Record your observations, paying
close attention to the miscibility of the contents.
8. Repeat Step 7 for each ester.
Analyze and Evaluate
(a) Write a chemical equation to represent each Figure 1  Use your hand to waft the smell of the ester toward you.
Do not hold the substance directly under your face.
reaction.  K/U
(b) What is the odour of each ester produced?  T/I
Apply and Extend
(c) Use your observations to write a statement about the
solubility of esters in water.  T/I (e) Suggest a use for each of your products.  A
(d) What is the function of the concentrated sulfuric acid (f) What must be done before the esters are used as you
in the reactions?  K/U suggested in (e)?  A

Investigation 1.6.3 OBSERVATIONAL STUDY Skills Menu

• Questioning • Planning • Analyzing

Making Soap • Researching
• Hypothesizing
• Controlling Variables
• Performing
• Evaluating
• Communicating
(Teacher Demonstration) • Predicting • Observing

To make soap, a reaction must occur between a strong Purpose

base and a triglyceride (fat or oil). To produce soap from the saponification of lard, vegetable
O shortening, or oils
CH2 O C(CH2)14CH3
Equipment and Materials
O
• chemical safety goggles
CH O C(CH2)14CH3  3 NaOH • lab apron
O sodium hydroxide • protective gloves
(or KOH, potassium hydroxide)
• wax pencil
CH2 O C(CH2)14CH3
• two 100 mL beakers
a fat • 250 mL beaker
saponification • forceps
• 50 mL graduated cylinder
• 2 glass stirring rods
CH2 OH
• balance
CH OH  3 CH3(CH2)14CO2Na • utility stand with ring clamp
CH2 OH • hot plate
• beaker tongs
glycerol a crude soap
• heat-resistant mat

NEL Chapter 1 Investigations   67

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 • thermometer 45 °C for this time. If the mixture spatters or bubbles,
• fi lter funnel and paper it is too hot. Remove the beaker from the hot plate
• fats (lard or vegetable shortening) and let it cool to below 45 °C. Return it to the hot
• oils (cooking oils such as corn oil, canola oil, olive oil) plate again. Record your observations.
WHIMIS Corrosive SM.ai
• WHIMIS
sodium hydroxide pellets, NaOH(s) (for teacher use
Flammable SM.ai
9. Continue heating the mixture until it has a
only) consistency similar to pudding, then turn off the hot
plate. Use tongs to move the beaker to the heat-
• ethanol
resistant mat. Allow the contents to cool. To colour
• vinegar, CH3COOH(aq)
the soap, add a drop or two of food colouring.
• sodium chloride crystals, NaCl(s)
10. Use the balance to measure 4 g of sodium chloride
• wash bottle containing distilled water crystals into beaker C. Add 20 mL of cold distilled
• food colouring (optional) water and stir until the salt is dissolved.
• perfume (optional) 11. Add the contents of beaker C to beaker B. Stir.
• paper towel
WHIMIS Corrosive .ai 12. Add 10 mL of vinegar. Record your observations.
Sodium hydroxide pellets are extremely corrosive to eyes
13. Carefully pour any excess liquid into the sink. Wash any
excess vinegar off the soap with about 10 mL of distilled
and skin. They must only be handled with forceps; gloves
water. Once again, pour off excess liquid in the sink.
must be worn. If sodium hydroxide comes into contact with
your skin, wash the affected area with a lot of cool water. If 14. Filter the soap mixture through a fi lter funnel and
sodium hydroxide contacts the eyes, it can cause blindness.
fi lter paper. Take care not to puncture the fi lter paper.
A few drops of perfume or scent can be added.
Flush the eyes with water at an eyewash station for at least
WHIMIS Flammable.ai
10 min and seek medical attention as soon as possible. 15. Dry the soap on the fi lter paper or remove the soap,
shape it, and dry it on a paper towel.
Ethanol is flammable. It should be used only in a well-
Do not use this soap on your skin. It may contain unreacted
ventilated area. There should be no open flames or other
sodium hydroxide. Wear protective gloves when handling the soap.
sources of ignition in the laboratory.
Icon_CautionHand.ai
SKILLS observations
Procedure HANDBOOK A1, A2.3, A3.2
Observe the colour and texture of the soap. Compare it
Note that this Procedure should be performed only by a to those of common commercial soaps, and record your
qualifi ed teacher. observations.
1. Label a 100 mL beaker with the letter “A,” a 250 mL
beaker with the letter “B,” and the second 100 mL Analyze and Evaluate
beaker with the letter “C.” (a) Write a word equation describing the reaction taking
2. Measure about 10 mL of distilled water into beaker A. place in Steps 8 and 9. Classify the reaction. T/I
3. Put on your safety goggles, lab apron, and protective (b) What was the purpose of adding vinegar in Step 12?
gloves. Write a balanced chemical equation describing the
4. Using forceps, carefully add 18 pellets of solid sodium reaction taking place. (Note that the molecular formula
hydroxide, a few at a time, to beaker A. Do not allow for ethanoic acid can be written as either CH3COOH(aq)
the pellets to touch your skin. Carefully stir the or HC2H3O2(aq).) Classify the reaction. T/I
sodium hydroxide pellets with a glass rod until they (c) What other substances may be in the fi ltrate aft er the
dissolve. Th e solution will get very hot as the sodium
soap was fi ltered out? K/u
hydroxide dissolves. Set beaker A aside to cool.
5. Use the balance to measure about 15 g of fat, such as Apply and Extend
lard or shortening, or oil, such as corn oil or olive oil, (d) Describe how saponifi cation and esterifi cation are
into beaker “B.” Add 15 mL of ethanol to the fat or oil. related. K/u
6. Put the beaker, supported by the ring clamp, on the hot
(e) Do you think soap molecules are polar or non-polar?
plate. Warm the mixture very gently. Stir with a glass rod
How would this aff ect their ability to remove oils from
until the fat and ethanol are melted and thoroughly mixed.
greasy surfaces? T/I A
Turn the hot plate off . Use beaker tongs to remove beaker
B and place it on a heat-resistant mat on the bench. (f) Research how soap was made historically. How were
7. Once the contents of beaker A have cooled, add them the reactants obtained? What were the hazards of the
to beaker B. process, and the benefi ts of the product? Present your
fi ndings in a format of your choice. T/I C A
8. Replace beaker B, inside the ring clamp, on the hot
plate. Heat it again very gently for 20 min, stirring WEB LINK
continuously. Keep the temperature between 40 and

68 Chapter 1 • Organic Compounds NEL

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 investigation 1.7.1 AcTiViTY SKIllS MENu

• Questioning • Planning • Analyzing

• Researching • Controlling Variables • Evaluating
Building organic Molecular • Hypothesizing • Performing • Communicating
Models • Predicting • Observing

Using molecular models of organic compounds, you will 2. For each reaction listed, choose an appropriate
demonstrate a variety of chemical reactions. reactant and make a model of this compound. Write
its name and structural formula in your table.
Purpose 3. Manipulate the model as indicated to create a model
To help diff erentiate between the structures of the reactant of the product. Add its name and structural formula
and the product of a reaction using molecular models to your table. Compare the models of the reactants
and products for structural changes.
Equipment and Materials 4. Supply the name of any missing reaction types in the
• molecular modelling kit table.
SKILLS
Procedure HANDBOOK A2.4, B.3 Part B
Part A 5. Draw a fl ow chart to show the synthesis of ethanoic
1. In Table 1, the columns specify the type of compound acid from ethene.
involved in the reaction, and the type of reaction. For 6. Build a molecular model of ethene and make changes
example, for Reaction 1, the reactant is an alkane and it to the model following the fl ow chart you created.
will undergo a substitution reaction. Copy Table 1 into
your notebook, leaving space to write the names and Analyze and Evaluate
structural formulas of reactant and product compounds.
(a) Create a concept map to summarize the various
Table 1 Organic Reactions reaction types. T/I C
(b) For which kinds of organic molecules are molecular
Reaction modelling exercises most eff ective? Explain. T/I
number Reactant Reaction type Product

1 alkane substitution
2 alkene addition
3 alcohol aldehyde
4 ether
5 aldehyde controlled
oxidation
6 chlorobenzene
7 controlled ketone
oxidation
8 esterification
9 amide
10 aromatic aromatic halide
compound

NEL Chapter 1 investigations 69

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