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Chapter 12: Alkanes Chapter Objectives (aka...What is going to be on the exam) 1.! ! What are the basic properties of organic compounds? Be able to identify organic compounds and the types of bonds contained in them.! 2.! ! ! What are functional groups, and how are they used to classify organic molecules? Be able to classify organic molecules into families by functional group. 3.! What are isomers? Be able to recognize and draw constitutional isomers. 4.! ! How are organic molecules drawn? Be able to convert between structural formulas and condensed or line structures. 5.! ! ! What are alkanes and cycloalkanes, and how are they named? Be able to name an alkane or cycloalkane from its structure, or write the structure, given the name 6.! ! ! What are the general properties and chemical reactions of alkanes? Be able to describe the physical properties of alkanes and the products formed in the combustion and halogenation reactions of alkanes. 1 Chapter 12: Alkanes 1. What are the basic properties of organic compounds? Organic chemistry is the branch of chemistry that deals with the study of carbon based compounds. Organic molecules have covalent bonds. Organic molecules contain polar covalent bonds when carbon bonds to an electronegative element on the right side of the periodic table. There are over 18 million known, and many more unknown possible structures ranging from one C to over a million carbons, and containing other elements such as N, O, S. ! ! ! 2 Chapter 12: Alkanes Carbon Review Carbon has 4 valence electrons and can form 4 bonds. Covalent molecules can form polar covalent or non polar covalent bonds. Hydrocarbons: 12.48 3 Chapter 12: Alkanes 2.! What are functional groups, and how are they used to classify organic molecules? Functional group: 12.27, 12.32 b, 12.33 4 Chapter 12: Alkanes 3.! What are isomers? Isomers: Constitutional Isomers: Different constitutional isomers are completely different chemical compounds with different structures, different physical properties and potentially different physiological properties. 12.36, 12.46 5 Chapter 12: Alkanes 4. How are organic molecules drawn? Condensed structure: Bond-line structure (skeletal structure): Conformers: 6 Chapter 12: Alkanes 5. ! What are alkanes and cycloalkanes, and how are they named? Alkane: Straight-chain alkane: Branched-chain alkane: 12.19, 12.21 7 Chapter 12: Alkanes Composed of a prefix that tells how many carbons there are Composed of a suffix that tells whether that the molecule is an alkane -ane Alkyl Group: ! 8 Chapter 12: Alkanes Naming Branched Alkanes, Alkenes and Alky Branched Alkanes 1. Name the longest chain. 2. Number that chain so as to give the lowest number priority to any branched groups. 3. Name the branched groups. 4. Write the full name as one word: a. Use hyphens to separate numbers from prefixes b. Use commas to separate numbers from other numbers c. Use alphabetical order to list branched groups Branched Alkenes and Alkynes 1. Name the longest continuous chain containing the double or triple bond. 2. Number the chain giving the lowest priority to the double or triple bond. 3. Write the full name as one word: a. Use hyphens to separate numbers from prefixes b. Use commas to separate numbers from other numbers c. Use alphabetical order to list branched groups d. If it is an alkene, do cis-trans isomers apply? 12.38, 12.23, 12.50, 12.52 9 Hydrocarbons ChapterCyclic 12: Alkanes Cycloalkanes yclic Alkanes H2C H2C CH2 H2C H2C CH2 H2C cyclobutane H2 C H2 C CH2 H2C CH2 cyclopropane H2C CH2 H2C CH2 C H2 cyclohexane H2C C H2 C H2 cyclopentane H2C CH2 CH2 H2C H2 C CH2 CH2 H2C CH2 H2C CH2 C H2 cycloheptane C H2 cyclooctane Cycloalkanes 1. Use cycloalkane name as the parent. Cyclic Alkenes andthe Alkynes H2C HC CH2 H C CH2 C C 2 HC 2. ! Identify and number the substituents. H C cyclopropene CH2 2 CH2 cyclooctyne 10 Chapter 12: Alkanes 6.! What are the general properties and chemical reactions of alkanes? 1. 2. 3. 4. 5. Reactions of Alkanes: Combustion: Halogenation: 12.70, 12.60, 12.62 11 Chapter 12: Alkanes Sample Problems 1. Draw and name the unbranched alkane with 5 carbons. 2. Draw and name all 5 isomers of hexane Sample Problems Circle and name each functional group: 3. ! Circle and name each functional group Draw: butane O propene 2-butene O 2-methyldecane cyclopentane O methylcyclohexane 3-methylcycloheptene HO Name: OH H O H H H2N O acetylsalicylic acid; aspirin testosterone; a steroid/sex hormone OH phenylalanine; an essential amino acid CH4 4. Problems: Name: 1) Draw and name the saturated, unbranched alkane with 5 carbons. 2) Draw all 5 isomers of hexane. 3) Draw 2-methyl-2-butene. Why is there no cis-trans isomers? Why do we not specify the location of the double bond in propene? Why is there no such compound known as methyne? 12