Chapter 10 REVIEW
Part 1
(Page 466)
1. B
2. A
3. B
4. 1, 2, 6, 9
5. 4, 5, 7, 8
6. D
7. C
8. D
9. 4, 2, 5, 7
10. 7, 5, 2, 4
11. 9, 1, 8, 3
12. 4, 2 (or 2, 4)
13. D
14. C
Part 2
(Page 467)
15. (a) organic halide
[It is not possible to draw a line structure.]
(b) organic halide
(c) alcohol
(d) alcohol
(e) carboxylic acid
(f) ester
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(g) aromatic alcohol
(h) aromatic organic halide
(i) aromatic carboxylic acid
(j) aromatic ester
16. (a) butane + chlorine o 2-chlorobutane + hydrogen chloride
[Another possible reaction can produce 1-chlorobutane.]
(b) but-1-ene + hydrogen chloride o 2-chlorobutane
[Another possible reaction produces 1-chlorobutane.]
(c) chloroethane + hydroxide ion o ethene + water + chloride ion
(d) benzene + fluorine o fluorobenzene + hydrogen fluoride
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(e) benzoic acid + ethanol o ethyl benzoate + water
(f) propene + bromine o 1,2-dibromopropane
(g) propan-1-ol + ethanoic acid o propyl ethanoate + water
17.
Propane is the least soluble of the molecules due to intermolecular bonding. Propane only has
London dispersion forces and, since it has the least number of electrons of the four, has the
weakest attraction to other molecules. In addition, the other three molecules have London
dispersion, dipoledipole, and hydrogen bonding forces, all of which allow these molecules
to form stronger bonds with water, which also has all three intermolecular forces. Stronger
forces of attraction between solute and solvent increase solubility.
18. Monomers of addition polymers generally contain double bonds and may have no other
functional groups. Condensation monomers contain two functional groups, such as carboxyl,
amine, or hydroxyl groups. There may be two different monomers and each monomer may
have the same or different functional groups at the ends.
Addition polymerization reactions only produce the polymer and no other product,
while condensation polymerization reactions produce the polymer as well as another, smaller
molecule such as water, ammonia, or hydrogen chloride.
19. Organic compounds require some special handling in the lab. Many of the chemicals are
volatile, and breathing the fumes can cause headaches, irritation to the respiratory tract,
intoxication, asthma attacks, and nausea. The lab area should be well ventilated and the
chemicals’ containers should be kept closed whenever possible. Organic compounds are often
flammable, so sparks or open flames should never be present in the lab. Heating organic
compounds should always be done carefully, over steam baths or hot plates kept on low heat.
Since organic chemicals are often used in pure form, they can be hazardous and irritating to
the skin, so lab aprons, eye protection, and gloves are recommended for use while working
with organic materials. Never mix organic chemicals as they may spontaneously react and
produce unpredictable results.
Many organic chemicals are toxic and do not easily break down in the environment.
Organic chemicals should not be poured down the sink or tossed into the trash. These
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chemicals should be placed into the appropriate waste container so that they can be disposed
of correctly.
20. Problem
What is the percent yield in the esterification reaction between pentanol and butanoic acid to
form pentyl butanoate?
Analysis
C5H11OH(l) + C3H7COOH(l) o C3H7COOC5H11(l) + H2O(l)
2.00 g m
88.12 g/mol
158.27 g/mol
1 mol
nacid 2.00g u
0.0227 mol
88.12 g
nester
mester
1
0.0227 mol
1
158.27 g
0.0227 mol u
3.59 g
1 mol
0.0227 mol u
or
mester
2.00 g acid u
1 mol acid
1 mol ester
158.27 g ester
u
u
= 3.59 g
1 mol ester
88.12 g acid
1 mol acid
1.32 g
u 100% = 36.7%
3.59 g
According to the stoichiometry and the evidence collected, the percent yield of the
esterfication reaction is 36.7%.
21. Alkanes are saturated; alkenes are unsaturated, containing a double bond. Alkenes tend to be
more reactive due to this double bond, so one possible test is to react each sample with
bromine water. The alkene will react much faster and remove the brown/orange colour from
the mixture.
Another test is to add potassium permanganate to each hydrocarbon sample. The
alkene will be oxidized into an alcohol, in the process removing the purple colour due to the
permanganate. This test is known as Baeyer’s test. The alkane will not react with potassium
permanganate, so the mixture will remain purple.
22. (a) 1,2-difluoropentane
(b) butan-1-ol
(c) pentanoic acid
(d) ethyl propanoate
(e) propane-1,3-diol
(f) propanoic acid
(g) propyl propanoate
(h) 1,3-dibromobutane
23. (a)
(b)
% yield =
(c)
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(e)
(f)
24. (a) addition polymers
(b) Teflon
monomer: tetrafluoroethene or tetrafluoroethylene
polystyrene
monomer: phenylethene or styrene
polypropylene
monomer: propene or propylene
polyvinyl chloride
monomer: chloroethene or vinyl chloride
(c) All of the monomers have a carbon-carbon double bond. The extra pair of electrons in the
double bond can be easily rearranged to provide two additional bonding electrons to form
a new bond with another monomer.
25. Condensation polymers require monomers with two functional groups to enable reactions
between adjacent monomers; both ends of each monomer must be capable of forming a bond
and, in the process, eliminating a smaller molecule such as water, ammonia, or hydrogen
chloride. The monomers bond together at the site where atoms are removed from their
functional groups.
26. The invention of synthetic polymers has had a profound impact on the environment and on
the social and economic prosperity of the “have” or developed countries of the world, but an
insignificant impact on poorer “have-not” countries. The following discussion will examine
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the impact of synthetic polymers from a variety of perspectives to determine whether
synthetic polymers benefit humanity.
The invention of synthetic polymers represents a great advance in both chemistry and
chemical engineering. Polymer chemists and engineers can now blend different combinations
of polymers and additives to produce new synthetic materials with a desired set of properties.
Often these “designer” materials have properties that are superior to those of natural
materials. For example, canoes made of a synthetic polymer are lighter and more durable than
those made from wood. The development of synthetic polymers has also had a positive social
impact on our society by allowing new beneficial devices such as artificial limbs, prosthetic
devices, and advanced building materials to be made. The development and manufacturing of
synthetic polymers is a major economic stimulus to the already wealthy developed countries
of the world. New polymers stimulate the development and marketing of new consumer
products, creating numerous jobs in a variety of sectors of the economy. Ironically, many
poorer rural regions of the world have the raw materials, such as oil, needed to manufacture
synthetic polymers. However, they lack the expertise, investment, and infrastructure to
convert these raw materials into finished products. Often these raw materials are exported to
developed countries that then process them into finished products.
Despite their social and economic benefits, synthetic polymers have been a major
ecological problem because:
Ɣ they are made from nonrenewable resources, and
Ɣ many are non-biodegradable, so will be around for a a very long time before they
degrade.
Currently, there are many alternatives to using materials made from synthetic
polymers. Food products, such as soft drinks, could be sold in glass returnable bottles. Plastic
food containers, such as the Styrofoam containers used by restaurants, could be replaced with
containers made from paper, a renewable resource. Plastic grocery bags could be replaced
with cloth bags that are used repeatedly.
Despite their negative environmental impact, synthetic polymers are now an integral
part of our way of life. If used wisely, the benefits of synthetic polymers outweigh their
drawbacks.
27. In order to achieve sustainable development of Alberta’s fossil fuel wealth, our society must
reduce the present rate of consumption of fossil fuels for (among other things) the production
of polymers. Wise and prudent use of this resource will ensure that sufficient supplies of
fossil fuels are available for future generations of Albertans.
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