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Chapter 1: Structure and Physical Properties of Organic Compounds

Chapter 1: Structure and Physical Properties of Organic Compounds Chapter 2: Reactions of Organic Compounds. UNIT 1: Organic Chemistry. UNIT 1. Chapter 1: Structure and Physical Properties of Organic Compounds. Chapter 1: Structure and Physical Properties of Organic Compounds.

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Chapter 1: Structure and Physical Properties of Organic Compounds

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  1. Chapter 1: Structure and Physical Properties of Organic Compounds Chapter 2: Reactions of Organic Compounds UNIT 1: Organic Chemistry

  2. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Chapter 1: Structure and Physical Properties of Organic Compounds For thousands of years, scientists and Aboriginal peoples have been isolating organic compounds from natural materials, such as birch bark. The properties of these compounds make them useful in a wide variety of applications. TO PREVIOUS SLIDE

  3. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 1.1 Introducing Organic Compounds • Until the late 1800s, “organic” meant matter from living systems. “Inorganic” meant matter from non-living systems. • Synthesis of urea (organic) from inorganic compounds forced scientists to reconsider their definitions. Modern Definitions TO PREVIOUS SLIDE

  4. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 The Special Nature of the Carbon Atom • Important atomic properties of carbon: • It is much more likely to share electrons than gain or lose electrons. Therefore, covalent bonding occurs. • It has four valence electrons. Therefore, it can be bonded to as many as four different atoms. Carbon can bond to four different atoms, producing a molecule with a tetrahedron shape. TO PREVIOUS SLIDE

  5. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 Isomers • Most organic molecules consist of more than one carbon atom bonded together in a chain or ring structure. • Molecules with the same molecular formula but atoms in different arrangements are known as isomers. • Constitutional orstructural isomers: molecules with the same molecular formula, but the atoms are bonded in a different sequence. These molecules are constitutional isomers. TO PREVIOUS SLIDE

  6. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 Isomers Stereoisomers: molecules with the same molecular formula and sequence of atoms, but they differ in the three-dimensional orientation of their atoms • diastereomer: stereoisomers based on the presence of a double bond • enantiomer: stereoisomers that are mirror-images of each other. These molecules are diastereomers. TO PREVIOUS SLIDE

  7. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 Learning Check Are the following molecules isomers? If so, what type of isomers are they? Answer on the next slide TO PREVIOUS SLIDE

  8. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 Learning Check • Yes they are isomers. • They are stereoisomers, not constitutional isomers. TO PREVIOUS SLIDE

  9. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.1 Section 1.1 Review TO PREVIOUS SLIDE

  10. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 1.2 Hydrocarbons Hydrocarbons are composed of only carbon and hydrogen. The different classes are: • cyclic hydrocarbons • alkanes • alkenes • aromatic hydrocarbons • alkynes TO PREVIOUS SLIDE

  11. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Drawing Hydrocarbons Five ways to represent hydrocarbon molecules are: • empirical molecular formula • condensed structural formula • expanded molecular formula • line structural formula • structural formula TO PREVIOUS SLIDE

  12. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Alkanes • Contain only single covalent bonds. • The general formula for straight and branched-chain alkanes: CnH2n+2. • When naming and drawing alkanes: identify the root, suffix, and prefix. TO PREVIOUS SLIDE

  13. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Alkenes • Contain one or more double bonds. • The general formula for straight and branched-chain alkenes: CnH2n. • When naming and drawing alkenes: identify the root, suffix and prefix. • For main chains with more than four carbons, the position of the double bond must be indicated. This alkene is named 3-ethyl-2,2-dimethylhex-1-ene. TO PREVIOUS SLIDE

  14. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Learning Check Name the following hydrocarbon and draw its condensed structural formula. Answer on the next slide TO PREVIOUS SLIDE

  15. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Learning Check The name is: pent-2-ene The condensed structural formula is: TO PREVIOUS SLIDE

  16. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Alkynes • Contain one or more triple bonds. • The general formula for straight and branched-chain alkynes: CnH2n-2. • When naming and drawing alkynes: identify the root, suffix, and prefix. • For main chains with more than four carbons, the position of the double bond must be indicated. 4-ethylhex-2-yne. TO PREVIOUS SLIDE

  17. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Cyclic Hydrocarbons • Contain carbon-based ring structures. Most are alkanes or alkenes. • The general formula for cyclic alkanes: CnH2n. • When naming and drawing cyclic hydrocarbons: identify the root, suffix, and prefix. • Carbon atoms of a multiple bond are numbered 1 and 2, and side groups are the lowest possible numbers. 3,4-dimethylcyclopentene TO PREVIOUS SLIDE

  18. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Aromatic Hydrocarbons • Hydrocarbons that are derived from benzene, C6H6. • When naming and drawing aromatic hydrocarbons identify the root and prefix. • If a benzene ring is bonded to a hydrocarbon chain that is more than six carbons long, the benzene ring is a phenyl side group. Benzene is best represented by the resonance hybrid structure. This aromatic hydrocarbon is 1-methyl-4-propylbenzene. TO PREVIOUS SLIDE

  19. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Learning Check A student has named a hydrocarbon as 1-ethyl-5-propylbenzene. Use a drawing of the structure to show why that name is incorrect. What is the correct name? Answer on the next slide TO PREVIOUS SLIDE

  20. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Learning Check The structure is shown below. Since the side groups should be identified using the lowest possible numbering, the correct name is 1-ethyl-3-propylbenzene TO PREVIOUS SLIDE

  21. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Physical Properties of Hydrocarbons • Hydrocarbons are non-polar (not soluble in water). • The shapes and sizes of hydrocarbons affect their boiling points. • Many aromatic compounds have strong odours. TO PREVIOUS SLIDE

  22. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.2 Section 1.2 Review TO PREVIOUS SLIDE

  23. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 1.3 Hydrocarbon Derivatives Hydrocarbon derivatives have one or more functional groups. TO PREVIOUS SLIDE

  24. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Hydrocarbon Derivatives TO PREVIOUS SLIDE

  25. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Alcohols • Contain a hydroxyl functional group, -OH • When naming and drawing alcohols, identify the • root (longest chain with the –OH group) • suffix (add –ol to the end of the parent alkane name) • prefix (name and number the alkyl side groups) The addition of an –OH group to a hydrocarbon increases the polarity of the molecule. TO PREVIOUS SLIDE

  26. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Haloalkanes • Contain one or more halogen atoms (F, Cl, Br, I). • When naming and drawing haloalkanes, identify the • root (longest chain with the halogen) • suffix (use the alkane name) • prefix (name and number the alkyl side groups and halogens) 1,3-dichloro-3-fluoro-2methylbutane TO PREVIOUS SLIDE

  27. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Learning Check Draw the structural formula for fluoroethane. Explain why numbers are not required in the prefix of the name. Answer on the next slide TO PREVIOUS SLIDE

  28. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Learning Check Because there are only two carbon atoms, the number 1 is not used in the prefix to designate the position of the halogen. TO PREVIOUS SLIDE

  29. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Aldehydes • Contain a formyl group. • When naming and drawing aldehydes, identify the • root (longest chain with the formyl group) • suffix (ends in –al) • prefix (name and number the alkyl side groups) 3,4-dimethylpentanal TO PREVIOUS SLIDE

  30. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Ketones • Contain a carbonyl group bonded to two carbons. • When naming and drawing ketones, identify the • root (longest chain with the carbonyl group) • suffix (position of the carbonyl carbon is indicated and ends in -one) • prefix (name and number the alkyl side groups) Butanone TO PREVIOUS SLIDE

  31. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Carboxylic Acids • Contain a carboxyl group. • When naming and drawing carboxylic acids, identify the • root (longest chain with the carboxyl group) • suffix (ends in –oic acid ) • prefix (name and number the alkyl side groups) 2-ethylhexanoic acid TO PREVIOUS SLIDE

  32. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Learning Check What functional group do aldehydes, ketones, and carboxylic acids have in common? Answer on the next slide TO PREVIOUS SLIDE

  33. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Learning Check The carbonyl group TO PREVIOUS SLIDE

  34. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Esters • Contain a carbonyl group with another oxygen singly bonded to the carbon. • When naming and drawing esters, identify the • root (the “acid part”) • suffix (ends in –oate ) • prefix (alkyl group on oxygen and on the main chain) TO PREVIOUS SLIDE

  35. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Ethers • Contain an oxygen atom singly bonded to two carbon atoms (R-O-R′) • When naming and drawing ethers, identify the • root (longest chain, or R group) • suffix (ends according to the main chain) • prefix (indicate the alkoxy group then side groups) An ether is composed of an alkoxy group and parent alkane chain that are connected by an oxygen. TO PREVIOUS SLIDE

  36. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Amines Primary (R-NH2), secondary (R2-NH), or tertiary (R3-N) • When naming and drawing amines, identify the • root (longest chain bonded to the nitrogen) • suffix (ends in –amine and indicate position of the N) • prefix (indicate alkyl groups on N) TO PREVIOUS SLIDE

  37. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Amides • Contain a carbonyl group bonded to a nitrogen • When naming and drawing amides, identify the • root (longest chain with the carbonyl) • suffix (ends in -amide ) • prefix (alkyl groups on N, then on main chain) TO PREVIOUS SLIDE

  38. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Learning Check • Draw the condensed structural formula for each of the following: • Methylethanoate • b. 1-ethoxypropane • c. N-ethylpentamide Answer on the next slide TO PREVIOUS SLIDE

  39. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Learning Check • b. • c. TO PREVIOUS SLIDE

  40. UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds Section 1.3 Section 1.3 Review TO PREVIOUS SLIDE

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