1 Organic Chemistry Chapters 20 – 21

2 Carbon All living matter Four bonds Double and triple bonds

3 Diamond Colorless crystalline solid Extremely high melting point Conducts heat very well Does not conduct electricity Covalent network bonding Bonded to four nearest neighbors

4 Graphite Crumbles easily Feels greasy Atoms arranged in thin layers Weak London dispersion forces Layers slide past each other Conducts electricity

5 Fullerenes Formed when carbon-containing materials are burned with limited oxygen Nearly spherical C 60 Most stable Called buckminsterfullerene or buckyball

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7 Organic compounds Covalently bonded compounds containing carbon Except: Carbonates and oxides

8 Catenation Covalent bonding of an element to itself to form chains or rings Carbon can also double or triple bond to itself

9 hydrocarbons Contain only carbon and hydrogen Simplest organic compounds

10 Structural formula Regular or condensed Carbon makes four bonds, hydrogen makes one Hydrogen is understood to bond to the atom next to it

11 Draw the condensed structural formulas

12 Geometric isomers Order of atom bonding is the same, but arrangement of atoms is space is different Need rigid structure in molecule Double or triple bond Need two carbons each with two different groups attached Cis and trans isomers

13 Cis isomer Like groups on same side of carbon atoms

14 Trans iosmer Like groups on opposite sides of carbon atoms

15 Alkanes AKA saturated hydrocarbons Hold maximum amount of hydrogen Contain only single bonds General formula C n H 2n+2

16 Cycloalkanes Carbons arranged in ring Fewer hydrogen atoms – no free ends General formula C n H 2n

17 propane vs. cyclopropane

18 Simplified cycloalkane structure Carbon at each corner Enough hydrogen so each carbon has four bonds

19 IUPAC International Union of Pure and Applied Chemistry Systematic naming system

20 Unbranched chain alkanes Count carbon atoms for prefix Table 20-3, page 636 And suffix -ane

21 You try

22 Branched-chain alkanes Branches are alkyl groups Table 20-4, page 637

23 Alkane nomenclature 1. Name the parent hydrocarbon Longest continuous carbon chain Might be bent Name as straight-chain alkane

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25 Alkane nomenclature 2. Add the names of the alkyl groups In front alphabetize Add prefixes if necessary (di-, tri-, tetra-, penta-, etc.)

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27 Alkane nomenclature 3. Number the carbon atoms in parent alkane Give lowest numbers to alkyl groups If two possibilities, make the first alkyl group in name have lowest number 4. Insert position numbers Before alkyl group names

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29 Alkane nomenclature 5. Punctuate Hyphens between numbers and names Commas between numbers

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31 You try Name the molecule above octane

32 You try Name the molecule above 3-ethyl-2,4,5-trimethyloctane

33 You try Name the molecule above 5-butyl-2,2-dimethylnonane

34 Example Draw the condensed structural formula for 3,3,4- triethyl-4-methylhexane.

35 You try Draw the condensed structural formula for 3- ethyl-2,2-dimethylpentane.

36 Alkenes Unsaturated hydrocarbons Have at least one double bond

37 Alkene nomenclature 1. Name the parent hydrocarbon Longest continuous carbon chain containing double bond Might be bent Add suffix –ene if only one double bond If two, -adiene Three, - atriene Etc.

38 Alkene nomenclature 2. Add the names of the alkyl groups 3. Number the carbon atoms in parent alkene First carbon in double bond nearest end of chain has lowest number If two possibilities, number from end nearest first alkyl groups

39 Alkene nomenclature 4. Insert position numbers Double-bond position numbers before parent alkene name Before alkyl group names 5. Punctuate

40 Example Name the following alkene.

41 You try Name the following alkene

42 You try Draw 1,3-butadiene

43 Alkynes Contain at least one triple covalent bond.

44 Alkyne nomenclature 1. Name the parent hydrocarbon Longest continuous carbon chain containing triple bond Might be bent Add suffix –yne if only one triple bond If two, -adiyne Three, - atriyne Etc.

45 Alkyne nomenclature 2. Add the names of the alkyl groups 3. Number the carbon atoms in parent alkyne. First carbon in triple bond nearest end of chain has lowest number If two possibilities, number from end nearest first alkyl groups

46 Alkyne nomenclature 4. Insert position numbers Triple-bond position numbers before parent alkyne name Before alkyl group names 5. Punctuate

47 You try Name the following compound

48 You try Draw 3,3-dimethyl-1-butyne

49 Aromatic hydrocarbons Contain six-membered benzene ring Delocalized electrons

50 Aromatic hydrocarbon nomenclature 1. Name the parent hydrocarbon Benzene 2. Add the names of the alkyl groups 3. Number the carbon atoms in ring 1 goes with alkyl group that comes first alphabetically Number in the direction that gives the rest of the groups the lowest numbers

51 Aromatic hydrocarbon nomenclature 4. Insert position numbers 5. Punctuate

52 You try Name the following compound

53 You try Draw 1-ethyl-2-methylbenzene

54 Functional Group Responsible for specific properties Often site of chemical reactivity

55 Alcohols Contain hydroxyl group (OH) General formula R-OH R stands for the rest of the molecule

56 Alcohol nomenclature 1. Name the parent compound. Longest continuous chain that contains the hydroxyl group If one hydroxyl group – drop –e from alkane name, add –ol If more than one, keep –e and add –diol, -triol, etc.

57 Alcohol nomenclature 2. Number the carbon atoms in the parent chain Hydroxyl groups have lowest numbers possible 3. Insert position numbers Place hydroxyl number(s) immediately before parent name 4. Punctuate Separate numbers from name with hyphen Separate numbers with commas

58 You try Name the following compound.

59 You try Draw 1,2,3-butanetriol

60 Alkyl halides One or more halogen atoms replace hydrogen atom(s) General formula R-X

61 Alkyl halide nomenclature 1. Name the parent compound. Longest continuous carbon chain Add prefixes for halogen (fluoro-, chloro-, bromo-, or iodo-) in alphabetical order If more than one atom of a single halogen, add prefix di-, tri-, etc

62 Alkyl halide nomenclature 2. Number the carbon atoms in the parent chain Lowest numbers Lowest number to the first halogen name 3. Insert position numbers 4. Punctuate

63 You try Name the following compound.

64 You try Draw 1-bromo-1,3,5-trichloropentane

65 Ethers Two alkyl groups bonded to the same oxygen atom General formula R-O-R´ R and R´ can be the same or different

66 Ether nomenclature 1. Name the parent compound Ether 2. Add the names of the alkyl groups Alphabetical order Prefix di- if needed 3. Leave appropriate spaces in name Between alkyl names and before ether

67 You try Name the following compound

68 You try Draw dipropyl ether

69 You try Draw cyclopentyl methyl ether.

70 Aldehydes and Ketones Contain carbonyl group Aldehydes have it at end of chain Ketones have it in middle of chain

71 Aldehyde nomenclature 1. Name the parent compound Longest chain containing carbonyl group Change final –e to -al

72 Example Name the following compound

73 You try Draw octanal

74 Ketone nomenclature 1. Name the parent compound Longest chain containing carbonyl group -e to –one 2. Number the carbon atoms Carbonyl group has lowest number 3. Insert position numbers Carbonyl number in front of name 4. Punctuate

75 Example Name the following

76 You try Name the following

77 You try Draw 2-pentanone

78 Carboxylic acids Contain carboxyl group Always at end of chain

79 Carboxylic Acid Nomenclature 1. Name the parent compound If one carboxyl group, change –e to –oic acid If two carboxyl groups, -dioic acid.

80 Esters Contain carboxylic acid groups in which the hydrogen has been replaced by an alkyl group

81 Ester Nomenclature 1. Name the parent compound Name carboxylic acid Change –oic acid to –oate 2. Add the name of alkyl group Front of name 3. Leave space Between alkyl group and parent compound

82 Example Name the following compound.

83 You try Name the following compound.

84 You try Draw propyl ethanoate

85 Amines Derivatives of ammonia Functional group does not contain oxygen

86 Amine nomenclature Uses common names, not IUPAC 1. Name the parent compound Ends in –amine 2. Add the names of the alkyl groups Alphabetical order Prefixes di- or tri- if necessary

87 Amines Primary – one H replaced Secondary – two H replaced Tertiary – three H replaced

88 Substitution reactions One or more atoms replace another atom or group of atoms in a molecule Used to create alkyl halides

89 Addition Reactions An atom or molecule is added to an unsaturated molecule and increases the saturation fo the molecule

90 Hydrogenation Hydrogen atoms added to unsaturated molecule Converts oils (liquids) to fats (solids)

91 Condensation Reactions Two molecules or parts of the same molecule combine A small molecule, like water, is usually removed Used to form proteins from amino acids

92 Elimination Reaction A simple molecule, like water or ammonia, is removed from adjacent carbon atoms of a larger molecule Occurs in reactions in which sulfuric acid is a dehydrating agent

93 Polymer Large molecule made of many small units joined by organic reactions

94 Monomers Small units that make up polymers

95 Copolymer Made from two or more different monomers

96 Thermoplastic polymer Melts when heated Can be reshaped

97 Thermosetting polymer Does not melt when heated Keeps original shape

98 Linear polymer Molecules free to move Easily slide past each other Thermoplastic

99 Branched polymer Side chains prevent sliding Often thermoplastic

100 Cross-linked polymer Adjacent molecules are bonded together Can’t slide past each other thermosetting

101 Addition polymer Formed by chain addition reactions between monomers with double bonds

102 Vulcanization Natural rubber is thermoplastic Adding sulfur to molten rubber makes the rubber form cross links More durable

103 Condensation polymers Formed by condensation reactions Monomers must contain two functional groups Usually copolymers with alternating monomers