Chapter 10 REVIEW Part 1 Part 2

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Unit 5 Solutions Manual. 391. (g) aromatic alcohol. (h) aromatic organic halide. (i) aromatic carboxylic acid. (j) aromatic ester. 16. (a) butane + chlorine ...
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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