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Chapter 17 Organic Chemistry 17.2 Alkenes, Alkynes, and Polymers 1 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Unsaturated Compounds: Alkenes and Alkynes Unsaturated compounds • have fewer hydrogen atoms attached to the carbon chain than alkanes • are alkenes with C=C double bonds • are alkynes with triple C≡C bonds 2 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Alkenes and Alkynes The names of alkenes and alkynes • use the corresponding alkane names • change the end to ene for alkenes • change the end to yne for alkynes 3 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Alkenes and Alkynes 4 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Alkenes and Alkynes 5 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Example of Writing an Alkene Name Write the IUPAC name for the following: CH3 | CH3─CH=C─CH3 6 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Example of Writing an Alkene Name (continued) STEP 1 Name the longest carbon chain that contains a double or triple bond. butene STEP 2 Number the carbon chain starting from the end nearer the double or triple bond. CH3 | CH3─CH=C─CH3 4 7 Basic Chemistry 3 2 1 Copyright © 2011 Pearson Education, Inc. Example of Writing an Alkene Name (continued) STEP 3 Give the location and name of each substituent (alphabetical order) as a prefix to the alkene or alkyne name. CH3 | CH3─CH=C─CH3 2-methyl-2-butene 4 8 Basic Chemistry 3 2 1 Copyright © 2011 Pearson Education, Inc. Learning Check Write the IUPAC name for the following: Br CH3─CH─CC─CH3 9 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Solution STEP 1 Name the longest carbon chain that contains a double or triple bond. pentyne STEP 2 Number the carbon chain starting from the end nearer the double or triple bond. Br CH3─CH─C≡C─CH3 5 10 Basic Chemistry 4 3 2 1 Copyright © 2011 Pearson Education, Inc. Solution (continued) STEP 3 Give the location and name of each substituent (alphabetical order) as a prefix to the alkene or alkyne name. Br CH3─CH─C≡C─CH3 5 4 3 2 1 4-bromo-2-pentyne 11 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Learning Check Draw the condensed structural formula for 2-methyl-3-hexyne. 12 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Solution STEP 1 Draw the main chain of carbon atoms. For 3-hexyne, there are six carbon atoms in the chain, with a triple bond between carbons 3 and 4, C─C─C≡C─C─C STEP 2 Number the chain and place the substituents on the carbons indicated by the numbers. CH3 C─C─C≡C─C─C 1 13 Basic Chemistry 2 3 4 5 6 Copyright © 2011 Pearson Education, Inc. Solution (continued) STEP 3 Add the correct number of hydrogen atoms to give four bonds to each C atom. CH3 CH3─CH─C≡C─CH2─CH3 1 2 3 4 5 6 2-methyl-3-hexyne 14 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Polymers Polymers are • large, long-chain molecules • found in nature, including cellulose in plants, starches in food, and proteins and DNA in the body • also made synthetically, for example, polyethylene and polystyrene, Teflon, and nylon • made up of small repeating units called monomers • made by reaction of small alkenes 15 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Synthetic Polymers in Everyday Items 16 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Polymerization In polymerization, small repeating units called monomers join to form a long-chain polymer. 17 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Some Alkenes and Their Polymers 18 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Learning Check What is the name and condensed structural formula of the starting monomer for polyethylene? 19 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Solution Ethene (ethylene) CH2=CH2 20 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Learning Check Name the monomer used to make Teflon, and use four monomers to draw the condensed structural formula of a portion of a Teflon polymer. 21 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Solution F F │ │ F─C═C─F tetrafluoroethene (monomer) F F F F F F F F │ │ │ │ │ │ │ │ ─C─C─C─C─C─C─C─C─ │ │ │ │ │ │ │ │ F F F F F F F F 22 Basic Chemistry portion of Teflon Copyright © 2011 Pearson Education, Inc. Recycling Plastics Recycling is simplified by using codes found on plastic items. 23 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Learning Check What type of plastic is indicated by each of the following codes? A. 3 PVC B. 5 PP C. 6 PS 24 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Solution A. 3 PVC Polyvinyl chloride B. 5 PP Polypropylene C. 6 PS Polystyrene 25 Basic Chemistry Copyright © 2011 Pearson Education, Inc.