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chem 1152 survey of chemistry ii

www.karentimberlake.com. The John Hopkins School of Medicine flatly states:that we cannot say we know what a disease is until we know its chemistry, and organic chemical principles are at the heart of this knowledge.. www.karentimberlake.com. The study of structures, properties, and synthesisof organic compounds.Organic Chemistry is at the core of the study for those seeking education in :BiochemistryMedicinal ChemistryPharmaceutical chemistryPolymer chemistryMolecular BiologyPrima14

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chem 1152 survey of chemistry ii

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    1. www.karentimberlake.com

    2. www.karentimberlake.com

    3. www.karentimberlake.com What is Organic Chemistry??

    4. www.karentimberlake.com Contain carbon Have covalent bonds Have low melting points Have low boiling points Burn in air (oxygen) Are soluble in nonpolar solvents Form large molecules

    5. www.karentimberlake.com Vital Force Theory

    6. www.karentimberlake.com Discovery

    7. www.karentimberlake.com Present

    8. www.karentimberlake.com Organic vs. Inorganic Covalent bonding (nonpolar) Made of Carbon bonded to each other and other nonmetals Small attraction between molecules Ionic bonding Made of metals and nonmetals Strong attraction between molecules Water soluble

    9. www.karentimberlake.com Molecular Polarities

    10. www.karentimberlake.com Lewis Model of Bonding Nitrogen forms 3 covalent bonds and has one unshared pair of electrons .. . N . . Carbon forms 4 covalent bonds w/ no unshared pairs . . C . .

    11. www.karentimberlake.com Lewis Model of Bonding Hydrogen forms 1 covalent bonds w/ no unshared pair of electrons H . Oxygen forms 2 covalent bonds w/ 2 unshared pairs .. . O . ..

    12. www.karentimberlake.com Lewis Model of Bonding Chlorine(and fluorine, bromine, and iodine as well) forms 1 covalent bonds w/ 3 unshared pairs of electrons .. . Cl: ..

    13. www.karentimberlake.com Structure of Organic Compounds

    14. www.karentimberlake.com Learning Check

    15. www.karentimberlake.com

    16. www.karentimberlake.com Structure of Organic Compounds

    17. www.karentimberlake.com Structure of Organic Compounds

    18. www.karentimberlake.com Alkanes Functional Group Haloalkanes

    19. www.karentimberlake.com What is a functional group??

    20. www.karentimberlake.com Functional Groups Part of an organic molecule where chemical reactions take place Composed of an atom or group of atoms Replace an H in the corresponding alkane Provide a way to classify organic compounds Serve as basis for naming organic compounds

    21. www.karentimberlake.com Some Types of Functional Groups Haloalkane -F, -Cl, -Br CH3Cl Alcohol -OH CH3OH Ether -O- CH3-O-CH3 Aldehyde Ketone

    22. www.karentimberlake.com More Functional Groups Carboxylic acid -COOH CH3COOH Ester -COO- CH3COOCH3 Amine -NH2 CH3NH2 Amide -CONH2 CH3CONH2 Thiol -SH CH3SH

    23. www.karentimberlake.com Alkanes and Aromatic Hydrocarbons Organic Compounds Bonding in Hydrocarbons Naming Alkanes Properties of Alkanes

    24. www.karentimberlake.com Alkanes Contain C and H only Contain single bonds C-C Have 4 bonds to every carbon (C) atom Are nonpolar

    25. www.karentimberlake.com Complete Structural Formulas Show the bonds between each of the atoms H H ? ? H ? C ? H H C H ? ? H H CH4 , methane In methane, CH4 the four valence electrons of carbon are shared with the single electrons of four hydrogen (H) atoms. Each pair of electrons is a single bond, which can be drawn as a line. When a structure is drawn to show each bond, it is called a complete structural formula.In methane, CH4 the four valence electrons of carbon are shared with the single electrons of four hydrogen (H) atoms. Each pair of electrons is a single bond, which can be drawn as a line. When a structure is drawn to show each bond, it is called a complete structural formula.

    26. www.karentimberlake.com More Alkanes H H Condensed Structural Formulas H C C H CH3 CH3 H H Ethane H H H H C C C H CH3 CH2 CH3 H H H Propane The complete structural formula for ethane shows the single bonds between two carbon atoms and six H atoms. The complete structural formula of propane shows the 3-carbon chain with single bonds to the attached H atoms. To write a condensed structural formula, the H atoms are written as a group next to their respective C atoms. The complete structural formula for ethane shows the single bonds between two carbon atoms and six H atoms. The complete structural formula of propane shows the 3-carbon chain with single bonds to the attached H atoms. To write a condensed structural formula, the H atoms are written as a group next to their respective C atoms.

    27. www.karentimberlake.com Nomenclature

    28. www.karentimberlake.com Alkyl Groups Branches on carbon chains H H C CH3 methyl H H H H C C CH3CH2 ethyl H H An alkyl group is composed of one or more carbon atoms attached to a carbon chain. An alkyl group is derived from an alkane by removing one hydrogen. The ending –ane of the alkane is changed to –yl. The carbon branch from methane is the methyl group. The carbon branch from ethane is the ethyl group.An alkyl group is composed of one or more carbon atoms attached to a carbon chain. An alkyl group is derived from an alkane by removing one hydrogen. The ending –ane of the alkane is changed to –yl. The carbon branch from methane is the methyl group. The carbon branch from ethane is the ethyl group.

    29. www.karentimberlake.com IUPAC Names Name # carbons Structural Formula Methane 1 CH4 Ethane 2 CH3CH3 Propane 3 CH3CH2CH3 Butane 4 CH3CH2CH2CH3 Pentane 5 CH3CH2CH2CH2CH3 The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.

    30. www.karentimberlake.com IUPAC NAMES Name # carbons Structural Formula Hexane 6 CH3CH2CH2CH2CH2CH3 Heptane 7 CH3CH2CH2CH2CH2CH2CH3 Octane 8 CH3CH2CH2CH2CH2CH2CH2CH3 Nonane 9 CH3 CH2 CH2CH2CH2CH2CH2CH2CH3 Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

    31. www.karentimberlake.com Learning Check Alk1 A. What is the condensed formula for H H H H H C C C C H H H H H B. What is its molecular formula? C. What is its name?

    32. www.karentimberlake.com Solution Alk1 A. CH3CH2CH2CH3 B. C4H10 C. butane

    33. www.karentimberlake.com Alkanes and Aromatic Hydrocarbons Branched Alkanes Structural Formulas

    34. www.karentimberlake.com Branched Alkanes CH3 CH3CHCH3 methyl groups CH3 CH3 CH3CHCH2CHCH3 In the structural formula of an alkane, the alkyl group is typically attached vertically above or below the carbon chain.In the structural formula of an alkane, the alkyl group is typically attached vertically above or below the carbon chain.

    35. www.karentimberlake.com Naming Summary 1. Count the C’s in the longest chain 2. Name each attached group 3 Count the longest carbon chain to give the first attached group the smallest number 4. Name and locate each group

    36. www.karentimberlake.com Naming Branched Alkanes CH3 methyl branch CH3CH2CH2CHCH2CH3 6 5 4 3 2 1 Count Branches on carbon chains H H C CH3 methyl H A branched-chain alkane is named by indicating the attached groups on the longest carbon chain. In this example, the longest carbon chain has 6 carbon atoms. A branched-chain alkane is named by indicating the attached groups on the longest carbon chain. In this example, the longest carbon chain has 6 carbon atoms.

    37. www.karentimberlake.com Naming Branched Alkanes CH3 methyl branch CH3CH2CH2CHCH2CH3 6 5 4 3 2 1 Count 3-Methylhexane on third C CH3 six carbon chain group The chain is numbered to give the side group or methyl group a location on carbon 3 in the chain. The chain is numbered to give the side group or methyl group a location on carbon 3 in the chain.

    38. www.karentimberlake.com Learning Check Alk4 A. CH3 CH3 CH3CHCH2CHCH3 B. CH3 CH3 CH3CH2CHCH2CCH2CH3 CH3

    39. www.karentimberlake.com Solution Alk4 A. CH3 CH3 CH3CHCH2CHCH3 2,4-dimethylpentane B. CH3 CH3 CH3CH2CHCH2CCH2CH3 CH3 3,3,5-trimethylheptane

    40. www.karentimberlake.com Learning Check Alk5 Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

    41. www.karentimberlake.com Solution Alk5 A. 3,4-dimethylheptane CH3 CH3CH2CHCHCH2CH2CH3 CH3 2,2-dimethyloctane CH3 CH3CCH2CH2CH2CH2CH2CH3 CH3

    42. www.karentimberlake.com Nomenclature

    43. www.karentimberlake.com Nomenclature

    44. www.karentimberlake.com Nomenclature

    45. www.karentimberlake.com Nomenclature

    46. www.karentimberlake.com Branched Chain Alkyl Groups

    47. www.karentimberlake.com Nomenclature

    48. www.karentimberlake.com Nomenclature

    49. www.karentimberlake.com Nomenclature

    50. www.karentimberlake.com Isomers Same molecular formula Same number and types of atoms Different arrangement of atoms Structural isomers are compounds that have the same molecular formula with different arrangements of the atoms.Structural isomers are compounds that have the same molecular formula with different arrangements of the atoms.

    51. www.karentimberlake.com Isomers

    52. www.karentimberlake.com Recognizing Isomers

    53. www.karentimberlake.com Examples of Isomers The formula C4H10 has two different structures CH3 CH3CH2CH2CH3 CH3CHCH3 Butane 2-methylpropane When a CH3 is used to form a branch, it makes a new isomer of C4H10.

    54. www.karentimberlake.com Learning Check Alk6 Write 3 isomers of C5H12 and name each.

    55. www.karentimberlake.com Solution Alk7 Write the structural formulas of 3 isomers that have the formula C5H12. Name each. CH3CH2CH2CH2CH3 pentane CH3 CH3 CH3CHCH2CH3 CH3CCH3 CH3 2-methylbutane 2,2-dimethylpropane

    56. www.karentimberlake.com Haloalkanes An alkane in which one or more H atoms is replaced with a halogen (F, Cl, Br, or I) CH3Br 1-bromomethane Br (methyl bromide) CH3CH2CHCH3 2-bromobutane

    57. www.karentimberlake.com Substituents List other attached atoms or group in alphabetical order Br = bromo, Cl = chloro Cl Br CH3CHCH2CHCH2CH2CH3

    58. www.karentimberlake.com Substituents List other attached atoms or group in alphabetical order Br = bromo, Cl = chloro Cl Br CH3CHCH2CHCH2CH2CH3 4-bromo-2-chloroheptane

    59. www.karentimberlake.com Learning Check HA2 The name of this compound is: Cl CH3 CH3CH2CHCH2CHCH3

    60. www.karentimberlake.com Solution HA2 The name of this compound is: Cl CH3 CH3CH2CHCH2CHCH3 4-chloro-2-methylhexane

    61. www.karentimberlake.com Haloalkanes as Anesthetics Halothane (Fluothane) F Cl F C C Br F H Fluothane is a haloalkane that is widely used as an anesthetic, which is a compound that decreases the ability of the nerve cells to conduct pain.

    62. www.karentimberlake.com Ozone Layer Ozone layer Stratosphere (10-30 miles Above Earth)

    63. www.karentimberlake.com ozone O3 layer absorbs most of the sun’s harmful radiation. CFCs - chlorofluorocarbons - are depleting that ozone layer. CFCs are used as Freons in refrigeration, air conditioning, and foam insulation. Their use in spray cans is no longer allowed. Chlorofluorocarbons CFCs and the Ozone Layer

    64. www.karentimberlake.com Chlorofluorocarbons and the Ozone Layer To become stable, the Cl? acquires an electron from ozone O3 and produces ClO. Cl? + O3 ClO + O2 The presence of ClO in the atmosphere is an indicator of the disappearance of ozone.

    65. www.karentimberlake.com Impact of Loss of Ozone Layer According to the National Academy of Sciences, each 1% loss of ozone increases by 2% the amount of UV radiation reaching the earth. More UV radiation means more skin cancer and cataracts in humans, more intense photochemical smog, and lower crop yields.

    66. www.karentimberlake.com Alkanes and Aromatic Hydrocarbons Cycloalkanes

    67. www.karentimberlake.com Chlorofluorocarbons and the Ozone Layer In the stratosphere, the CFCs react with the high-energy UV radiation from the sun UV light CF2Cl2 CF2Cl? + Cl? Freon-12 free radical

    68. www.karentimberlake.com Cyclic Hydrocarbons

    69. www.karentimberlake.com Line –Angle Drawing

    70. www.karentimberlake.com Cycloalkanes Cyclopropane CH2 CH2 CH2 Cyclobutane CH2 CH2 CH2 CH2 The is a group of alkanes that have a cyclic structure. These cycloalkanes contain a carbon chain that is in a ring. Each cycloalkane has a formula that is 2C less than the corresponding alkane. For example, propane is C3H8 whereas cyclopropane ic C3H6. Butane is C4H10 and cyclobutane is C4H10. The names of the cyclic structures use the prefix cyclo in from of the alkane name for the carbon chain.The is a group of alkanes that have a cyclic structure. These cycloalkanes contain a carbon chain that is in a ring. Each cycloalkane has a formula that is 2C less than the corresponding alkane. For example, propane is C3H8 whereas cyclopropane ic C3H6. Butane is C4H10 and cyclobutane is C4H10. The names of the cyclic structures use the prefix cyclo in from of the alkane name for the carbon chain.

    71. www.karentimberlake.com More Cycloalkanes Cyclopentane CH2 CH2 CH2 CH2 CH2 Cyclohexane CH2 CH2 CH2 CH2 CH2 CH2

    72. www.karentimberlake.com Naming Cycloalkanes with Side Groups Number of Naming side groups 1 Side group name goes in front of the cycloalkane name. 2 or more Number the ring in the direction that gives the lowest numbers to the side groups.

    73. www.karentimberlake.com Cycloalkanes with Side Groups

    74. www.karentimberlake.com Learning Check Alk8

    75. www.karentimberlake.com Solution Alk8

    76. www.karentimberlake.com Learning Check HA1 Name the following:

    77. www.karentimberlake.com Solution HA1 Name the following: bromocyclopentane 1,3-dichlorocyclohexane

    78. www.karentimberlake.com Shapes of Alkanes

    79. www.karentimberlake.com Shapes of Cycloalkanes

    80. www.karentimberlake.com Shapes of Alkanes and Cycloalkanes

    81. www.karentimberlake.com Shapes of Alkanes and Cycloalkanes

    82. www.karentimberlake.com Cis –Trans Isomerism

    83. www.karentimberlake.com Cis –Trans Isomerism

    84. www.karentimberlake.com Cis –Trans Isomerism

    85. www.karentimberlake.com Physical Properties

    86. www.karentimberlake.com Physical Properties

    87. www.karentimberlake.com Physical Properties

    88. www.karentimberlake.com Physical Properties

    89. www.karentimberlake.com Fractional Distillation

    90. www.karentimberlake.com Reactions of Alkanes Combustion alkane + O2 CO2 + H2O + heat

    91. www.karentimberlake.com Combustion In the Cell Metabolic oxidation is combustion C6H12 O6 + 6O2 6CO2 + 6H2O + heat glucose

    92. www.karentimberlake.com Learning Check Alk2 Complete the combustion reaction for C3H8 + O2 + Balance your equation

    93. www.karentimberlake.com Solution Alk2 Step 1 C3H8 + O2 CO2 + H2O Step 2 C3H8 + O2 3 CO2 + 4 H2O Step 3 C3H8 + 5 O2 3 CO2 + 4 H2O To balance the atoms in the formula C3H8, we place a coefficient of 3 in front of CO2 and a coefficient of 4 in front of H2O. The total O in the products is 10 O (6 O in 3CO2 and 4 O in 4 H2O). To balance the 10 O, a coefficient of 5 is placed in front of the O2.To balance the atoms in the formula C3H8, we place a coefficient of 3 in front of CO2 and a coefficient of 4 in front of H2O. The total O in the products is 10 O (6 O in 3CO2 and 4 O in 4 H2O). To balance the 10 O, a coefficient of 5 is placed in front of the O2.

    94. www.karentimberlake.com Learning Check Alk3 Complete and balance the reaction for the complete combustion of C7H16

    95. www.karentimberlake.com Solution Alk3 Step 1 C7H16 + O2 CO2 + H2O Step 2 C7H16 + O2 7 CO2 + 8 H2O Step 3 C7H16 + 11 O2 7 CO2 + 8 H2O The carbon has a subscript 7, which means we need to place a coefficient of 7 in front of CO2. The H subscript 16 is balanced by placing a coefficient of 8 in front of H2O. Finally, the total O of 22 ( 14 + 8) indicates that a coefficient of 11 in front of O2 will balance the O atoms.The carbon has a subscript 7, which means we need to place a coefficient of 7 in front of CO2. The H subscript 16 is balanced by placing a coefficient of 8 in front of H2O. Finally, the total O of 22 ( 14 + 8) indicates that a coefficient of 11 in front of O2 will balance the O atoms.

    96. www.karentimberlake.com Reactions of Alkanes Halogenation of Alkanes (Substitution) alkane + halogen light/heat haloalkane CH4 + Cl2 CH3Cl + HCl

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