Review. Knowledge/Understanding. FeBr 3 + I 2 + HI. polymerization biochemistry. monosaccharide starch. (a) CH 3 CH 2 CHCH CH 3 CH 2 CHCOH

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1 Review Reflecting on Chapter 2 Summarize this chapter in the format of your choice. ere are a few ideas to use as guidelines: Describe the different types of organic reactions, and give an example of each type. Compare addition polymerization reactions with condensation polymerization reactions. List the biomolecules you learned about in this chapter, and give an example of each. List some benefits of the use of organic compounds. List some risks from the use of organic compounds. Reviewing Key Terms For each of the following terms, write a sentence that shows your understanding of its meaning. addition reaction substitution reaction elimination reaction oxidation reduction condensation reaction hydrolysis reaction esterification reaction Markovnikov s rule monomers polymer addition polymerization plastics nylons condensation polyamides polymerization biochemistry polyesters amino acids protein saccharide carbohydrate disaccharide monosaccharide starch polysaccharide nucleotides DNA (2-deoxyribonucleic lipids acid) oils RNA (ribonucleic acid) fats waxes Knowledge/Understanding 1. Describe each type of organic reaction, and give an example. (a) addition (b) substitution (c) elimination oxidation (e) reduction (f) condensation (g) hydrolysis 2. What is the connection between a condensation reaction and an esterification reaction? 3. ow is an addition reaction related to an elimination reaction? 4. (a) In your own words, define an esterification reaction and a hydrolysis reaction. Give two examples of each type of reaction. (b) Explain the connection between these two types of reactions. 5. Identify each reaction as an addition reaction, a substitution reaction, or an elimination reaction. (a) I (b) (c) Cl 2 2 Cl + 2 (e) ( ) 2 + Br ( )(Br) (f) () 2 2 (g) 2 Br + N 3 2 N 2 + Br 6. Identify each reaction as an oxidation or a reduction. (xidizing and reducing agents are not shown.) (a) 2 2 (b) (c) + I C 2 2 FeBr 3 + I C Chapter 2 Reactions of rganic Compounds MR 105

2 7. Describe each type of polymerization, and give an example. (a) addition polymerization (b) condensation polymerization 8. What is the difference between a nylon and a polyester? ow are they similar? 9. ow can the following reaction be an example of both an addition reaction and a reduction? (a) What is Markovnikov s rule? Why does it apply to the following reaction? 2 + Br? (b) Name and draw the two isomeric products of this reaction. (c) Which product is formed in the greater amount? 11. Classify the following oxidation as an addition, substitution, or elimination reaction. Explain your reasoning. 2 + [] 12. Consider the reaction of an aldehyde with lithium aluminum hydride, LiAl 4, to produce an alcohol. Why is this reaction a reduction, not an oxidation? 13. A short section of the polymer polypropene is shown below. 2 ( ) 2 ( ) (a) Draw and name the monomer that is used to make this polymer. (b) What type of polymer is polypropene? Explain your reasoning. (c) What is the common name of this polymer? 14. (a) What is the difference between a protein and an amino acid? (b) ow are proteins important to living organisms? 15. (a) Define the term lipid. (b) Give three different examples of lipids. (c) List four foods you eat that contain lipids. ow are lipids important to your body? 16. (a) Distinguish between monosaccharides, disaccharides, and polysaccharides. (b) Draw and name an example of each. (c) ow are carbohydrates important to living organisms? 17. (a) What is the generic monomer of a polysaccharide polymer? (b) What is the monomer of cellulose? Inquiry 18. Draw and name the product(s) of each incomplete reaction. (int: Do not forget to include any second products, such as 2 or Br.) (a) + Br 2 (b) Br (c) 2 (e) (f) 2 + 2S 4 3 (g) (h) 19. Draw the product(s) of each incomplete reaction. int: Do not forget to include the second product, such as 2 or Br, for a substitution reaction. (a) 2 C (b) 2 C + Cl 2 (i) + Cl 2 (ii) (c) + [] 2 S [] C S 4 (e) C + [] S 4 2 S MR Unit 1 rganic Chemistry

3 (f) 2 C 2 ( ) 2 + (i) (major product) + (ii) (minor product) (g) [] (i) + [] (ii) (h) (i) 2 (Br) + (j) (k) polymerization (l) n( 2 ) 7 + nc Draw and name the reactant(s) in each reaction. (a)? (b)? + [] C 2 (c) C C +? C C (e)? +? 2 C (f)? + [] (g)? + [] (h)? 2 S 4 + Cl 2 + Cl 2? + []? FeBr C n 2 polymerization Cl C + [] + 2 Cl C Br Br (i)? polymerization Identify each type of reaction in questions 18, 19, and (a) Write a brief procedure that you could use to carry out the following reactions in a laboratory. oxidation of 1-pentanol oxidation of 2-pentanol oxidation of 2-methyl-2-butanol (b) Describe the results you would expect. (c) Write a chemical equation for each reaction. Show the products, if any. 23. In Investigation 1-A in Chapter 1, you carried out a condensation reaction to produce an ester called ethyl ethanoate. In this chapter, you learned about the reverse reaction: hydrolysis. (a) Write a balanced chemical equation, showing the reactants and the products of the hydrolysis of ethyl ethanoate. (b) Write a step-by-step procedure to carry out the acid hydrolysis of ethyl ethanoate. (c) List the materials and equipment you would need to carry out this reaction. 24. At the beginning of section 2.2, you learned about Tollen s reagent. Tollen s reagent oxidizes aldehydes to produce the salt of a carboxylic acid. ow does this reagent work as a test to distinguish between aldehydes and ketones? 25. ne type of condensation reaction (which you did not study in this chapter) takes place when an acid, usually 2 S 4, is added to an alcohol at temperatures that are lower than the temperatures for an elimination reaction. In this type of condensation reaction, two alcohol molecules combine to form an ether. A water molecule is eliminated as a second product of the reaction. (a) Write a chemical equation to show the condensation reaction of ethanol to produce ethoxyethane. Chapter 2 Reactions of rganic Compounds MR 107

4 (b) Classify this condensation reaction as an addition reaction, a substitution reaction, or an elimination reaction. Explain your answer. (c) A different reaction occurs if the acid Cl is used instead of 2 S 4. Name this type of reaction, and write the equation for it. Communication 26. Use a molecular model kit to build an example of a DNA nucleotide monomer. Join your nucleotide to your classmates nucleotides to build a short strand of DNA. 27. Make a list of five materials or substances you use every day that are made from organic compounds. Write a paragraph that describes how your life would be different without these five materials or substances. 28. ow has organic chemistry helped to solve the problems caused by the use of the following substances? (a) leaded gasoline (b) CFCs Making Connections 29. Suppose that the Canadian government proposed a $3 million grant to scientists who are working on the development of synthetic pesticides. Would you support this grant? Write a brief paragraph that explains your point of view. 30. Styrofoam clamshells were used for packaging fast food until a few years ago. Today, large fast food corporations use paper packaging instead. Why has Styrofoam use been reduced? What problems does this product cause? Research Styrofoam (made from a polymer called polystyrene) to answer these questions. 31. Do you think Canada should cut back on the manufacture and use of synthetic polymers? Write a brief paragraph that explains your point of view. Include at least three good reasons to back up your point of view. If necessary, research the information you need. 32. Steroids are one type of lipid. Research answers to the following questions. (a) What is the structure of a steroid? (b) What are some common examples of steroids? ow are steroids used in medicine? (c) ow are steroids misused in sports? 33. Muscle-building athletes sometimes drink beverages that contain amino acids. (a) Why might this type of drink help to build muscles? (b) Research the benefits and risks of this type of drink. 34. Early settlers in Canada often made their own soap using animal fats and lye. (a) What type of chemical would you expect lye to be? Explain your reasoning. (b) Use a reference book or dictionary to find the chemical name for lye. (c) Look through books about early pioneer life to find an early recipe for making soap. Use the recipe you found to write a full laboratory procedure for making soap like the early settlers did. Include a list of materials and a diagram, if necessary. Answers to Practice Problems and Short Answers to Section Review Questions Practice Problems: 1.(a) substitution (b) addition (c) elimination 2.(a) oxidation (b) reduction (c) reduction 3.(a) addition/reduction (b) condensation/substitution 4.(a) addition (b) oxidation 5. 3-ethyl-3-heptanol 6.(a) 1-bromohexane (minor), 2-bromohexane (major) (b) 2-methyl-2-pentanol (major), 2-methyl-3-pentanol (minor) 8.(a) propene + hydrochloric acid (b) ethene + bromine (c) 3-methyl-2-pentene, 2-ethyl-1-butene hydrogen gas 9.(a) substitution (b) oxidation (c) substitution elimination 11. (a) elimination (b) oxidation (c) substitution substitution (e) oxidation (f) substitution 12.(a) 1-butene + water (b) pentanal, pentanoic acid (c) 2-bromo-3-methylbutane + water 2-methyl-1-propanol + NaBr (e) butanone (f) chlorocyclohexane + water 13. no, because tertiary alcohols cannot be oxidized. 14.(a) reduction (b) reduction (c) reduction esterification (e) hydrolysis 15.(a) cyclobutanone, cyclobutanol; 2,2,4,4-tetramethyl-3- pentanone, 2,2,4,4-tetramethyl-3-pentanol 16.(a) hexanoic acid (b) 1-octanol (c) methyl propanoate + water 1-propanol + ethanoic acid (e) 3-hexanol (f) 2-propyl (or isopropyl) 3-methylpentanoate 17.(a) 2-methylbutanal (b) 1-pentanol, pentanal (c) 1-propanol, 3-methylhexanoic acid 18. polymethylmethacrylate (PMMA) 19.(a) condensation (b) addition (c) condensation 21.(a) addition (b) condensation; nylon (c) condensation; polyester condensation; polyester 108 MR Unit 1 rganic Chemistry

5 Section Review: 2.1: 1.(a) addition (b) elimination (c) substitution substitution 2.(a) oxidation (b) reduction (c) reduction oxidation (e) reduction 3.(b) hydrolysis 2.2: 1.(a) elimination (b) addition (c) oxidation reduction or addition (e) substitution (f) substitution (g) condensation 2.(a) 2,3-dibromobutane (b) 1-chlorobutane (minor) + 2-chlorobutane (major) (c) 1-hexene + water 3,3-dimethyl-1-butene + Br 3.(a) bromobenzene (b) 1-bromopentane + water 4.(a) 2-pentanone (b) propanoic acid (c) 2,3-dimethylbutanal ethane (e) 3-pentanol (f) 1-butene, butane (g) 2-ethyl-3,4- dimethyl-1-octanol 5.(a) 2-propyl propanoate (b) cyclopentene (c) methanoic acid, 2-butanol cyclohexanol (e) N-ethyl heptanamide 6.(b) 2-bromo-4-methylpentane 7.(a), (c), and 2.3: 1.(a) protein, starch, nucleic acid (b) insulin, amylose, DNA (c) amino acid, monosaccharide (glucose), nucleotide 2.(a) addition (b) condensation 3.(a) addition polymerization (b) condensation polymerization (c) condensation polymerization 5.(a) amino acid (b) monosaccharide (c) amino acid lipid (e) disaccharide Chapter 2 Reactions of rganic Compounds MR 109