Web Activities
UNIT 1: ORGANIC CHEMISTRY
Chapter 1 – Organic Compounds
Section 1.2 questions
p. 23
Question 5
a. Use the information in Table 3, to plot a graph
showing the relationship between the number of carbon atoms and the
boiling points of the alkanes. Describe and propose an explanation for
the relationship you discover.
b. Research a use for each of the first 10 alkanes, and suggest why
each is appropriate for this use.
Summary
of the Properties and Uses of Hydrocarbons
A table containing information about a dozen hydrocarbons, and a brief
discussion of their reactivity trends. This AUS-e-TUTE site has been
created by science teachers.
Hydrocarbons:
Alkanes and Alkenes
A table containing links to general information about hydrocarbons,
especially alkanes and alkenes, along with links to information about
certain molecules. This site belongs to a group of websites from the
United Kingdom called the Department of Education's Grid for Learning.
Boiling
Points of Alkanes
A small table demonstrating increasing boiling point for larger hydrocarbon
chain lengths.
Octane
and Car Engines
From Marshall Brain's How Stuff Works website, this page explains octane
in relation to the gasoline that we use in our cars. It also briefly
explains recent developments in the gasoline and automobile industries.
Natural
Gas and its Processing
This corporate website provides an introduction to natural gas, explaining
its composition and properties. It then explains how natural gas is
extracted, de-contaminated, and fractionated into its various components.
Organic
Chemistry: An Introduction
From VisionLearning, an educational web portal, this site provides a
excellent overall introduction to organic chemistry. It begins with
the properties of carbon, and moves gradually through alkanes, alkynes,
isomerism, and the importance of functional groups.
Section 1.3 questions
p. 31
Question 7
TNT is an explosive with a colourful history (Figure 5).
Research and report on who discovered it, and its development, synthesis,
uses, and misuses.
Detecting
Explosives
From the Sailor Research Group of the University of San Diego, this
site actually addresses the development of detectors for explosives.
In doing so, it mentions some of the properties of TNT that make it
a good explosive.
The
Commercial Explosives Industry
This page, from the Institute of Makers of Explosives (IME), describes
the social and technological history of explosives, specifically explaining
the impact that advances in explosive technology have had in our daily
lives.
Explore an Issue
p. 35
Role Play: Can We Afford Air Conditioning?
Re: CFC’s and alternative coolants. “Imagine that
a committee is set up to decide whether the new model should have air
conditioning using HFC-134a, or no air-conditioning unit at all.”
a. Costs can be measured in many ways: financial, social, environmental,
political, etc. Choose one way of assessing cost and collect and sort
information to help you decide whether the costs of automobile air conditioners
are justified.
b. Select a role for yourself–someone who would be concerned about
the kinds of costs that you have researched. Consider how this person
might feel about the issue of air conditioning.
c. Role-play the meeting, with everyone taking a turn to put forward
his/her position on whether the new car model should have air conditioning.
d. After the “meeting,” discuss and summarize the most important
points made. If possible, come to a consensus about the issue.
Industry
Pledge on Greenhouse Gases
This page contains a reporter's description of the 1999 meeting of the
annual Earth Technologies forum, in which the leaders of many industries
came together to discuss emission reductions of sulfur hexafluoride,
PFCs, and CFCs.
Fluorocarbons
and Sulphur Hexafluoride
The Web site is dedicated entirely to explaining the effects of fluorocarbons
on the environment. Click on topics in the menu on the left to learn
about various fluorocarbons, where they are used, and their effect on
the environment.
Cooling
Without Warming
Mitsubishi provides this web-page explaining the movement from car air
conditioners using CFCs to those using HFCs. It introduces the idea
of now moving to carbon dioxide instead of either of the above fluorocarbons,
in order to avoid increased greenhouse gas emissions.
Ontario
and Manitoba to Ban CFCs in Cars
This Canadian Press reporter informs us that Ontario and Manitoba will
be limiting further use of CFCs, especially in the air conditioners
of older cars. The article explains some of the benefits of such a policy,
but also mentions criticisms by some environmental groups of the new
policy.
Practice
p. 37
Question 7
Why are some organic halides toxic while others are not? And
why are some organisms affected more than others? Use the Internet to
find out, using the following key words in your search: bioaccumulation;
fat soluble; food chain. Report on your findings in a short article
for a popular science magazine or website.
Sample
solution is regarding DDT Bioaccumulation and Biomagnification
This website summarizes the manner in which pollutants enter an ecosystem,
as well as their tendency to concentrate as they move through trophic
levels. It provides case studies on DDT and the Long Island Estuary,
and mentions various federal acts relating to heavy metal pollution.
Bioaccumulation
This Oregon State University site defines bioaccumulation, explains
its process, and talks about the subject in terms of the dynamic equilibrium
that exists both within individual organisms, but also throughout an
entire ecosystem.
Bioaccumulation
Studies in Streams
This site provides links to the results of monitoring projects that
keep track of certain bioaccumulation markers in certain streams across
the United States.
Sediment
Toxicity and Bioaccumulation Testing
Coastal Bioanalysts Incorporated is a company that performs bioaccumulation
testing, and in this website they explain the various methods that they
use to complete this testing.
Section 1.4 questions
p. 37
Question 5
Why was mustard gas such an effective weapon, both during World
War I and more recently? Research its properties and effects, and what
defences have been developed against it.
Mustard
Gas
This researcher at Bristol University in England explains the composition
and past use of mustard gas, and then goes on to explore the use of
mustard gas as a therapeutic agent for cancer patients. The article
also provides many links to other articles and websites that relate
to mustard gas.
Mustard
Gas: Toxicity Frequently Asked Questions
This list of frequently asked questions about mustard gas is provided
by the Agency for Toxic Substances and Disease Registry. It provides
lots of information, especially for someone who thinks they might have
been exposed to mustard gas.
Mustard
Gas Exposure and Long-Term Health Effects
The Department of Veteran Affairs provides this Fact Sheet regarding
the long-term effects of mustard gas on war veterans.
Section 1.4 questions
p. 37
Question 6
Shortly after the connection was made between the “hole”
in the ozone layer and the release of chlorofluorocarbons, many manufacturers
stopped using CFCs as propellants in aerosol cans.
a. Research what alternatives were developed, and the effectiveness
of each in the marketplace. Are the alternatives still in use? Have
any of them been found to cause problems?
b. Design a product (one that must be sprayed under pressure) and its
packaging. Plan a marketing strategy that highlights the way in which
your product is sprayed from the container.
Aerosols
in the Stratosphere
This website provided by the United States Environmental Protection
Agency (EPA) explores the link between aerosols in the stratosphere
and ozone depletion. It not only provides useful graphs, but also several
links to other EPA pages with information about ozone depletion.
Aerosol
Propellants
This information page is provided by the Alliance for Responsible Atmospheric
Policy. It explains the preponderance of aerosol products in consumer
goods, and proposes that substiting HFCs into such products is the environmentally-responsible
solution.
Aerosol
Propellants
This page is part of a series entitled, "The Plain Man's Guide
to Aerosols." It explains how aerosol propellant cans work, and
introduces the various propellant liquids and gases that are used within
them.
Practice
p. 45
Question 10
a. Research the reactions, along with the necessary conditions,
that take place in a methanol-burning car engine.
b. What are the advantages and the disadvantages of methanol as a fuel,
over more conventional gasoline or diesel fuels.
c. Give arguments for and against the implementation of a law requiring
that all cars in Canada should be adapted to burn methanol.
Methanol:
The Clear Alternative
This site has been developed by the Methanol Institute to advertise
the first vehicle to make a cross-country trek in a methanol fuel-cell
car. It provides links to more information about the trek, as well as
links to other news and information items about methanol-powered cars.
Methanol
Vehicles
Maintained by the Alternative Fuels Data Center, this site provides
many useful specifications regarding methanol vehicles. It also provides
links to practical information regarding all alternative-fuel vehicles.
The
Alcohols - Ethanol and Methanol
This site belongs to a group of Transportation Energy websites managed
by EnergyQuest. Along with lots of information about alcohol-powered
vehicles, there are many links to other sites with information about
alternative fuels.
Section 1.5 questions
p. 48
Question 9
Alcohols have gained increased popularity as an additive to
gasoline, as a fuel for automobiles. “Gasohols” may contain
up to 10% methanol and ethanol, and are considered more environmentally
friendly than gasoline alone.
a. Write a balanced chemical equation for the complete combustion
of methanol and ethanol.
b. Although methanol is less expensive to produce, ethanol is blended
with methanol in gasoline. This is because methanol does not mix well
with gasoline, and ethanol is used as a co-solvent. Explain, with
reference to molecular structure, why ethanol is more soluble than
methanol in gasoline (which is mostly octane).
c. Methanol and ethanol are considered to be more environmentally
friendly that gasoline. Research, and explain why.
d. When small amounts of water are present in the gasoline in the
gas lines if a car, the water may freeze and block gasoline flow.
Explain how using gasohol would affect this problem.
Ethanol
General Information
This site is maintained by the Alternative Fuels Data Center. It provides
essential information on the potential use of ethanol as an energy source
in transportation. It provides many links to the major industry players
that recommend ethanol use in vehicles.
Ethanol
Information
Hosted by the American Coalition for Ethanol, this site advocates the
many benefits of blending ethanol with the currently-used form of gasoline.
It outlines the economic, agricultural, energy, and environmental benefits
of making the change.
Global
Climate Benefits of Methanol
This page hosted by the Methanol Institute briefly explores the climatic
advantages that might result by the adoption of methanol as an energy
source for vehicles. To access information on methanol fuel cells, click
on "fuel cells" in the middle of the page and then click on "fact sheets."
Section 1.6 questions
p. 57
Questions 8
Many organic compounds have been in everyday use for many years,
and are commonly known by nonsystematic names. Make a list of common
names of organic compounds found in solvents, cleaners, and other household
items. Conduct research using electronic or print resources to find
out the chemical name of five of these compounds, identify the functional
groups that are present, and discuss the useful properties that these
functional groups may impart to the compound.
Products
for Treatment for Condensation on Historic Glass and Storm Sash
This page belongs to a group of websites dedicated to "old-house
enthusiasts," and though its primary purpose is to describe methods
for cleaning glass, it also mentions in some detail the use of common
names to describe commonly used organic cleaning solvents.
CHCE's
HealtheHouse
This Web site lists compounds around the house that can be harmful to
children. Included on this list a a number of common household cleaners,
which have an organic chemical base.
Sources
of Indoor Air Pollution - Organic Gases
This web page from the United States Environmental Protection Agency
details the harmful effects of some common cleaners found around the
house.
Chemical
Hazards in the Home: Household Cleaners and Polishes
This pamphlet goes over the health and environmental
hazards of a number of household cleaners. Details about furniture polishes,
drain openers, and oven cleaners are included here.
Chemicals
in Home and Work Environments
This catalogue describes chemicals
that are found in home and workplace environments. Chemical and common
names are provided, along with a description of uses and occurences
of these substances in solvents, plastics, and gases.
Section 1.6 questions
p. 57
Question 9
The smell of formaldehyde was once common in the hallways of
high schools, as it was used a preservative of biological specimens.
This use has largely been discontinued.
a. What is the IUPAC name and structure of formaldehyde?
b. Why was its use as a preservative curtailed, and what substances
are being used in its place?
Formaldehyde
This encyclopedia.com entry provides a brief entry describing the chemical
formaldehyde and its uses.
Methods
of Fixation and Preservation
This site is managed jointly by the United States Antarctic Program
(USAP) and the National Museum of Natural History (NMNH). The page describes
the various mixtures that are used to preserve specimens, with several
recipes for making them, some with formaldehyde, some without.
Section 1.6 Questions
p. 57
Question 10
In cases of severe diabetes, a patient’s tissues cannot
break down glucose, and, instead, the body breaks down fat for its energy.
The fats are broken down in the liver and muscles, producing several
compounds called “ketone bodies,” one of which is acetone.
a. The acetone produced in this process is carried in the blood and
urine. Explain why acetone is soluble in these aqueous solutions.
b. When fats are the main source of energy production, there is an
overproduction of ketone bodies, leading to a condition called ketosis.
A patient with untreated diabetes may have a blood concentration of
acetone of 20 mg/ 100 mL. Convert this concentration to mol/L.
c. Acetone is volatile and is exhaled with the breath. Suggest a reason
why, like untreated diabetic patients, people who are severely starved
or dieting may have a smell of acetone on their breath – a diagnostic
symptom of ketosis.
d. Other ketone bodies lower blood pH, causing a condition called
acidosis, which can lead to coma and death. Research the symptoms
and effects of ketosis and acidosis and how these conditions may be
avoided.
Diabetic
Ketoacidosis
This page from MEDLINEplus details the causes, symptoms, and possible
treatments of diabetic ketoacidosis.
Diabetic
Emergencies and Anaesthesia
This 4um.com website provided by Pat Neligan provides an excellent overview
of diabetic emergencies, first by describing diabetes in general, and
then by relating these facts to the types of diabetic emergencies that
might result with anaesthesia.
Practice
p. 63
Question 10
Some cosmetic facial creams contain an ingredient manufacturers
call “alpha hydroxy,” which is designed to remove wrinkles.
These compounds are carboxylic acids that contain a hydroxyl group attached
to the C atom adjacent to the carboxyl group.
a. Explain why “alpha hydroxy” is an incorrect name for
any compound.
b. The alpha hydroxy acids in cosmetics may include glycolic acid,
lactic acids, malic acid, and citric acid. Research and draw structural
diagrams for these compounds.
c. In order to be absorbed through the skin, a substance must have
both polar and nonpolar components. Explain why these alpha hydroxy
acids are readily absorbed through the skin.
d. Over-the-counter creams may contain up to 10% alpha hydroxy acids,
while 25-30% concentrations are used by cosmetologists for “chemical
peels.” In each case, the ingredients cause the surface of the
skin to peel, revealing younger looking skin. Suggest reasons why
physicians recommend daily use of sun protection to accompany the
use of these facial creams.
Dupont
Glycolic Acid
This commercial website managed by DuPont provides the technical specifications
for glycolic acid, along with a full set of information including common
uses, safety, storage, and packaging.
Alpha
Hydroxy Acids for Skin Care
This article describes alpha hydroxy acids and lists what ingredients
are commonly inlcuded in alpha hydroxy skin creams. It also describes
possible harmful effects that these creams can have and ways to avoid
these effects.
Lactic
Acid
This site describes lactic acid, its biochemical
role in the body, its chemical structure, and its uses.
Malic
Acid
This site describes malic acid, its physical
properties, its chemical structure, and how it can be converted into
lactic acid through a process called malolactic fermentation.
Citric
Acid
This encyclopedia.com entry on citric acid describes the molecules structure
and properties. It also mentions, places where citric acid is found
and processes in which citric acid plays an important role.
Section 1.7 questions
p. 68
Question 8
Working with a partner or a small group, brainstorm and list
several occupations that require a knowledge of alcohols, carboxylic
acids, or esters. Research one of these careers and write a brief report
on the main strengths and qualities needed, academic training, and job
opportunities in the field.
Cool
climate Oenology and Viticulture Institute
This institute's website introduces the groups partnership with the
Wine Council of Ontario and the Ontario Grape Growers Marketing Board.
Links
to Ontario Wineries
This page lists all Ontario Wineries.
Perfumes
This site provides a very interesting description of the evolution of
the perfume industry in France. Along with economic descriptions, it
also provides a social history of such long-lasting, successful companies
like Chanel.
The
History of Perfume
This website provides links to pages that trace the evolution of perfume
back to the ancient Medes and Persian, right up until the 1990s.
Section 1.7 Questions
p. 68
Question 9
Tannic acid, originally obtained from the wood and bark of certain
trees, has for centuries been used to “tan” leather.
a. Give IUPAC name and chemical formula for tannic acid.
b. What effect does tannic acid have on animal hides? Explain your
answer with reference to the chemical reactions that take place.
Leather
and Tanning
This page describes tannic acid, its molecular formula and weight, its
properties, and its applications in medicine and food preparation.
Leather
Tanning
This site explains the origins of leather and the tanning process. The
cleaning, depilation, sweating, liming processes, as well as the two
methods of tanning are described.
History
and Process of Leather
This page describes the history of leather manufacturing
and the processes involved in the treatment of hide, including fleshing,
curing, pickling, and tanning.
Section 1.9 Questions
p. 82-83
Question 4
The flavour of almonds is obtained from benzyl methanal, also
called benzaldehyde. “Natural” almond flavour is extracted
from the pit of peaches and apricots, and may contain traces of the
poison hydrogen cyanide.
a. Write a structural diagram for benzaldehyde.
b. Write equations for a series of reactions in the synthesis of benzaldehyde
from an ester.
c. Research and describe the toxicity of the reactants listed in (b),
and compare the toxicity to that of hydrogen cyanide. In your opinion,
do your findings substantiate consumer perception that “natural”
products are always healthier that their “artificial”
counterparts.
Smell
Database: Hydrogen Cyanide
This University of Berkeley website provides some quick information
about hydrogen cyanide, including its overall chemical properties.
Hydrogen
Cyanide
This Bartleby.com website contains an entry from the Columbia Encyclopedia,
Sixth Edition, about the chemical, hydrogen cyanide. It describes some
overall properties, the chemical's uses, and information about where
it can be found in nature.
Chemical
Fact Sheet: Benzaldehyde
This page provided by Spectrum Laboratories consists of a large table
with the properties of, and facts about, benzaldehyde.
Materials
Safety and Data Sheet (MSDS): Benzaldehyde
This "MSDS Sheet" is the standardized information summary
about benzaldehyde, and includes information useful to a lab: safety
considerations, physical properties, and reactivity of the chemical.
Section 1.9 Questions
p. 83
Question 5
Quinine is a fairly effective treatment for malaria, a mainly
tropical disease that kills and incapacitates millions of people every
year. Quinine has a bitter taste and was mixed with lemon or lime to
make it palatable; it was later included as a components of a beverage
called tonic water.
a. Tonic water contains approximately 20 mg of quinine per 375-mL
can; the dosage required for the treatment of malaria is approximately
six 300-mg tablets per day. In your opinion, would drinking tonic
water be an effective approach to the treatment of malaria? Explain.
b. Refer to the structural diagram of quinine on p. xx, and explain
why quinine is soluble in water.
c. Research the effectiveness if quinine as an antimalarial agent
from the early 1800s to the present. Origins:
Quinine
This page from Rain Tree Nutrition gives a detailed history about quinine
and its application as an antimalarial drug.
History
of Malaria
This page provides an in-depth look at malaria. It includes several
useful diagrams including a map showing malarial prevalence around the
globe, a picture of the human body and the mosquito vectors that bear
the disease, and slides of the actual disease-causing parasite.
Quinine
This page is part of a series entitled, "Molecules of the Month."
It provides a brief overview of quinine, the first drug ever used to
combat malaria.
Investigation 1.5.2: Trends in Properties of Alcohols
p.86
Evidence
c. Using a print or electronic reference source, find the melting
point and the boiling point of each of the alcohols listed, and record
the information in your table. [alcohols – ethanol; 1-propanol;
1-butanol]
Alcohols
This "Journey into Science" webpage uses examples of molecules,
a chart and several questions to provide an introduction to various
alcohols.
Safety
(MSDS) Data for 1-Butanol
Read about the safety precautions for handling
of 1-butanol.
Safety
(MSDS) Data for 1-Propanol
Read about the safety precautions for handling
of 1-propanol.
Investigation 1.7.1: Properties of Carboxylic Acids
p. 88
Evidence
d. Using print and electronic resources, obtain the melting
point and boiling point for acetic acid and stearic acid, and record
them in the table.
Safety
(MSDS) Data for Acetic Acid
Read about the safety precautions for handling
of acetic acid.
Safety
(MSDS) Data for Stearic Acid
Read about the safety precautions for handling
of stearic acid.
Stearic
Acid
This site contains a table with some quick facts about stearic acid.
Material
Safety Data Sheet (MSDS): Glacial Acetic Acid
An MSDS contains standard and comprehensive information about chemicals,
especially regarding safety considerations, physical properties, and
reactivity, all of which are important pieces of information when using
acetic acid in a lab.
Chapter 1 Review
p. 97
Questions 15
Use print or electronic resources to obtain the molecular structure
of glucose, glycerol, and ethylene glycol. All three compounds have
a sweet taste.
a. Predict the relative melting points and boiling points
of rubbing alcohol, ethylene glycol, glycerol, and glucose. Give reasons
for your answer.
b. Predict the solubility of each of these compounds in water, and
in gasoline. Give reasons for your answer.
c. Ethylene glycol is toxic and is used as an antifreeze in automobile
radiators. Suggest a reason why car antifreeze must be stored safely
and spills must be cleaned up.
d. Do the structures of these three compounds support the hypothesis
that taste receptors respond to functional groups in the compounds
tasted? Explain.
Glucose
Structure
This page contains a 3-dimensional view of the glucose molecule. [**Please
note: You will likely need to download additional software to see the
picture.]
Carbohydrates
This site is the result of a partnership between Kennesaw State University
and the United States' National Science Foundation. It provides a brief
overview of carbohydrates, and talks about such molecules as sucrose,
cellulose, and glycerol.
Material
Safety and Data Sheet: Ethylene Glycol
An MSDS contains standard and comprehensive information about chemicals,
especially regarding safety considerations, physical properties, and
reactivity, all of which are important pieces of information when using
ethylene glycol in a lab.
Question 16
The distinction between “natural” and “synthetic”
products is usually based in the source of the product, whether it is
made by living organisms or by a laboratory procedure. Sometimes, the
product is in fact the same, but the distinction is made in the way
the product is processed. For example, when bananas are dissolved in
a solvent and the flavouring extracted, the pentyl ethanoate obtained
is labelled “natural flavour.” When pentyl ethanoate is
synthesized by esterification of ethanoic acid and pentanol, it is labelled
“artificial flavour.”
a. Write an equation for the synthesis of pentyl ethanoate.
b. In your opinion, what criteria should be used to distinguish a
‘natural’ product from a ‘synthetic’ product?
c. Research the differences in the source and processing methods of
vanilla flavouring. Write a report on your findings.
Vanilla
Extracts and Flavors
This website from the Vanilla.Company provides a very comprehensive
description of facts relating to vanilla, from general information to
specific details regarding various vanilla products.
Preparation
of ortho-Eugenol
Ortho-eugenol belongs to a class of compounds called vanilloids, and
this site describes the molecule, and explains how to prepare it in
a lab.
The
Determination of Vanillin in Vanilla Extract
This page is provided by the University of Malta's Department of Chemistry--it
outlines a very useful procedure for analysing the contents of vanilla
extract.
