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Ch. 13 Hydrocarbons Milbank High School. Objectives 1. What is organic chemistry? In general, how do organic compounds differ from inorganic compounds?

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Presentation on theme: "Ch. 13 Hydrocarbons Milbank High School. Objectives 1. What is organic chemistry? In general, how do organic compounds differ from inorganic compounds?"— Presentation transcript:

1 Ch. 13 Hydrocarbons Milbank High School

2 Objectives 1. What is organic chemistry? In general, how do organic compounds differ from inorganic compounds? 2. Why are there so many more organic compounds than inorganic compounds? 3. What are hydrocarbons? What structural features identify alkanes? Alkenes? Alkynes? Aromatic hydrocarbons? 4. How are alkanes, alkenes, alkynes, and aromatic hydrocarbons named using IUPAC nomenclature? 5. What are the physical and chemical properties of alkanes, alkenes, alkynes, and aromatic hydrocarbons?

3 Objectives 6. What is an alkyl group? 7. What are some products from reactions of alkanes? How are they formed? 8. What are the major reactions of alkenes? What are the products of those reactions? 9. What are polymers? How are they formed and utilized? 10. What is petroleum and how is it utilized?

4 Organic Chemistry Chemistry of compounds that contain carbon –Combine mainly with hydrogen, oxygen, and nitrogen –Over 10 million compounds made with these 4 elements 95% of compounds contain carbon –Form stable, covalent bonds with each other

5 Properties Organic (Benzene) –Low melting pts –Low boiling pts –Low solubility in water –Highly flammable –Nonconductive –Covalent bonds Inorganic (NaCl) –High melting pts –High boiling pts –Soluble in water –Nonflammable –Conductive –Ionic bonds

6 Hydrocarbons Compounds containing only two elements –Carbon and hydrogen

7 Sec Alkanes: Structures and Names Objectives –Identify an alkane –Determine what an isomer of an alkane is –Identify different types of alkanes

8 Alkanes Saturated Hydrocarbons Called saturated because each carbon is bonded to four other atoms Only single bonds Methane Ethane Propane

9 Homology Related compounds Homologs –Have properties that vary in a regular and predictable manner –A manner of organization –Similar to P.T.

10 Isomers Different compounds having the same molecular formula Butane Isobutane (isolated branched chain)

11 Isomers Pentane Isopentane Neopentane

12 Alkanes C n H 2n+2 Representation –Structural Formulas –Condensed Structural Formulas –Butane

13 Alkyl Group A group of atoms that results when one hydrogen atom is removed from an alkane C n H 2n+1 Change –ane ending to –yl Methyl Ethyl Propyl

14 Sec IUPAC Nomenclature Define IUPAC Examine the rules for IUPAC naming Determine the correct names of alkanes

15 IUPAC Nomenclature Geneva, Switzerland 1892 International Union of Pure and Applied Chemistry IUPAC System of Nomenclature –(isobutane, isopentane are common names)

16 IUPAC Rules 1. Name the longest chain in the parent compound. End in –ane. (Root name) –Number each carbon –See Example 2. Note the alkyl groups attached 3. Number the carbon that the group is attached to. –Must use the lowest number possible. –See Example

17 IUPAC Rules Con’t 4. Use prefixes to indicate the amount of attached groups –See Example 5. If there are more than two or more different substituents, list them in alphabetical order. If at equal points, lower alphabetical order given lowest number –See Example

18 IUPAC Rules Con’t 6. Prefixes not included in alphabetizing –See Example

19 Name each of the following

20 A. B. C. D.

21 a. 3-ethylhexane b.2,4-dimethylpentane c.c. 3-methylhexane d. 4-isopropylheptane Answers

22 Draw the structural formulas for each of the following 4-propylheptane 3-ethyl-2-methylpentane 3-isopropyl-3-methyloctane

23 Answers

24 Sec Properties of Alkanes Objectives –Determine the physical and physiological properties of alkanes

25 Physical Properties Nonpolar –Insoluble in water Less dense than water –Less than 1.0g/ml Related to one another –See chart Boiling points –Increase with higher molar mass

26 Physiological Properties Gases serve as anesthetics Liquid alkanes –Light liquids –Harmful to lungs –Heavy liquids Mineral oil Petroleum jelly

27 Sec Chemical Properties: Reactions of Alkanes Objectives –Determine the chemical properties of alkanes

28 Chemical Properties Do not react with many laboratory agents Usually very flammable –Undergo combustion reactions CH O 2  CO H 2 O + Heat 2 CH O 2  2 CO + 4 H 2 O (Harmful carbon monoxide reaction)

29 Sec Halogenated Hydrocarbons Objectives –Define what halogenated hydrocarbons are –Name halogenated hydrocarbons using common and IUPAC names

30 Halogenated Hydrocarbons Have one or more hydrogen atoms replaced by halogen atoms –Usually these are formed under UV light or very high temps –Results in an alkyl halide

31 Common Names First part of name is alkyl group Second part is the halogen, ending in –ide Name these: –CH 3 CH 2 Br –(CH 3 ) 2 CHCl –CH 3 I –CH 3 CH 2 CH 2 F

32 Answers Ethyl bromide Isopropyl chloride Methyl iodide Propyl flouride

33 IUPAC Names Rules similar to those used for naming alkanes Substitute in the prefixes fluoro-, chloro-, bromo-, and iodo-

34 Give the IUPAC name for each of the following compounds

35 Answers 2-chloropentane 4-bromo-2-methylhexane 2-chloro-3-methylbutane 1-bromo-3-chloro-4-methylpentane

36 Sec Cycloalkanes Define what a cycloalkane is Name and draw cycloalkanes

37 Cycloalkanes Carbon atoms that are joined in a ring or circle Simplest: cyclopropane Another: cyclohexane

38 Naming Add cyclo- Otherwise fairly similar to regular naming Draw structures for the following compounds –Cyclooctane –Ethylcyclohexane –1,1,2-trimethylcyclobutane

39 Answers A. B. C.

40 Draw these structures Cyclopentane 1-ethyl-2-methylcyclopentane 1-ethyl-1,2,5,5-tetramethylcycloheptane

41 Answers A. B. C.

42 Sec Alkenes Objectives –Define alkene –Name alkenes using IUPAC rules

43 Alkenes End in -ene Unsaturated hydrocarbons Have a double bond (CH 3 =CH 2 )

44 IUPAC Rules 1.Name the longest chain. 2.Indicate the position of the double bond with the lowest number possible. 3.Substituent groups named like alkanes 5-methyl-2-hexene

45 Name each of the following

46 Answers 6-dimethyl-2-heptene 2-ethyl-1-butene 4-ethyl-2-methyl-2-hexene 1-methylcyclohexene 2,4,4-trimethyl-2-pentene

47 Draw the structure for the following 3,4-dimethyl-2-pentene 3-ethyl-2-methyl-1-hexene 3-isopropylcyclopentene

48 Answers A. B. C.

49 Sec Properties of Alkenes Objectives –Determine the properties of alkenes

50 Properties of Alkenes Similar to alkanes Occur widely in nature Ethylene –Triggers fruit ripening –Can be used artifically Others –Carotene Vitamin A –Fruit coloring

51 Sec Chemical Properties: Reactions of Alkenes Define addition reactions Discuss hydrogenation and hydration Write equations for reactions between alkenes and other substances

52 Addition Reactions One of the bonds in the double bond is broken and each of the involved carbon atoms then bonds to another atom or group Hydrogenation—addition of hydrogen to an unsaturated molecule

53 Halogen addition Alkenes readily add halogen molecules

54 Hydration Addition of water to an alkene

55 Equations Write equations for the reaction between CH 3 CH=CHCH 3 and each of the following H 2 Br 2 H 2 O (H 2 SO 4 catalyst)

56 Answers

57 Write equations for the reaction of with each of the following. H 2 (Ni catalyst) Cl 2 H 2 O (H 2 SO 4 catalyst)

58 Answers.

59 Sec Alkynes Define alkyne Name alkynes using IUPAC naming rules

60 Alkynes Carbon atoms share 3 pairs of electrons, forming a triple bond Acetylene Alkynes have similar properties to those of alkanes and alkenes Naming is the same, except they end in -yne

61 Sec Benzene Objectives –Recognize the versatile structure of a benzene ring

62 Benzene Recognized by Michael Faraday in 1825 Six sided structure with single and double mobile bonds Resonance—a word used to describe the phenomenon in which no single Lewis structure can be used Figure 13.13

63 Sec Structure and Nomenclature of Aromatic Compounds Define and name aromatic hydrocarbons and aliphatic compounds Determine the difference between ortho, meta, and para distribution

64 Aromatic Compounds Benzene Named because thought to have strong aroma Now define as anything that has a benzene ring Aliphatic compounds—nonaromatic

65 Naming One substituent…easy

66 Naming 2 substituents…2 different ways One way…same as before Other way…uses the terms ortho, meta, and para –Ortho (1,2 distribution) –Meta (1,3 distribution) –Para (1,4 distribution)

67 Examples

68 Aryl Groups Sometimes Benzene rings attach to alkanes or alkenes Known as aryl groups Most common one is phenyl

69 Sec Uses of Benzene and Benzene Derivatives Objectives –Discuss some of the uses of benzene

70 Uses of Benzene Most comes from petroleum Used as a starting material Added to fuels to improve octane rating Cigarette smoke Very toxic In Nature.. –Tryptophan –Vitamin K –Folic acid –Many drugs…Table 13.12

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