Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Office Hours: MTW 8: :00 am; ThF 9: :00 am 1:00 - 2:00 pm. December 19, 2014: Test 1 (Chapters 12-13) January 26, 2015: Test 2 (Chapters 14-16) February 13, 2015: Test 3 (Chapters 17-19) March 2, 2015: Test 4 (Chapters 20-22) March 3, 2015: Make Up Exam: Chapters 12-22) Bring Scantron Sheet 882-E Chemistry 121(001) Winter CHEM 121 Winter 15

Slides & GHW Questions GHW#1 2 CHEM 121 Winter 15

Chapter 12. Saturated Hydrocarbons 12.1 Organic and Inorganic Compounds, Bonding Characteristics of the Carbon Atom, Hydrocarbons and Hydrocarbon Derivatives, Alkanes: Acyclic Saturated Hydrocarbons, Structural Formulas, Alkane Isomerism, Conformations of Alkanes, IUPAC Nomenclature for Alkanes, Line-Angle Structural Formulas for Alkanes, Classification of Carbon Atoms, Branched-Chain Alkyl Groups, Cycloalkanes, IUPAC Nomenclature for Cycloalkanes, Isomerism in Cycloalkanes, Sources of Alkanes and Cycloalkanes, Physical Properties of Alkanes and Cycloalkanes, Chemical Properties of Alkanes and Cycloalkanes, Halogenated Alkanes and Cycloalkanes, 371 3CHEM 121 Winter 15

1. Circle the correct compound type (ionic or covalent) for the following: formula compound type a) NBr 3 (ionic or covalent) b) NaCl (ionic or covalent) c) C 2 H 5 OH(inorganic or organic) d) NH 4 NO 3 (inorganic or organic) 4CHEM 121 Winter 15

Shapes of Atomic Orbitals – A s orbital consists of sphere with the center at the nucleus – A p orbital consists of two lobes arranged in a straight line with the center at the nucleus 5CHEM 121 Winter 15

Shapes of p Atomic Orbitals – A p orbital consists of two lobes arranged in a straight line with the center at the nucleus 6CHEM 121 Winter 15

Hybridizations of Atomic Orbitals – sp 3 tetrahedral  – sp 2 trigonal planar 120  – sp linear 180  7CHEM 121 Winter 15

Electronic Configuration of atoms Ground state electronic configuration Ground state electronic configuration of atoms in core format Carbon (C): [He] 2s 2, 2p 2 or [He] 2s 2, 2p x 1 3p y 1 3p z 0 Potassium (K): [Ar] 4s 1 Phosphorous (P):[Ne] 3s 2, 3p 3 Valence shell electronic configuration Carbon (C): 3s 2, 3p 2 Potassium (K): 4s 1 Phosphorous (P):3s 2, 3p 3 How you get the electronic configuration of an atom from the periodic table? 8CHEM 121 Winter 15

2.For the atoms and ions below, circle the correct ground state valence electron configuration of carbon in core format: a)Carbon (C):2s 1, 2p x 1 2p y 1 2p z 1 b)Carbon (C): 4s 1 or 3s 2, 3p 6 c)Carbon (C):[Ne] 3s 2, 3p 3 d) Carbon (C): [He] 2s 2, 2p x 1 2p y 1 2p z 0 9CHEM 121 Winter 15

Lewis structure of atoms (Review) Slide - 10CHEM 121 Winter 15

a) N b) C 3. Circle the Lewis structures of the following atoms: 11CHEM 121 Winter 15

Drawing Lewis structure molecules and ions (Review) 1)Add all valence electron 1)Add all valence electron of atoms in the molecule from the formula. Add the ion charge 2) Add the ion charge for negative ions or subtract for positive ions. Draw the skeletal structure 3) Draw the skeletal structure by connecting the atoms with single bonds. Give each of the atoms an octet 4) Give each of the atoms an octet (8 e-). Adding unshared pairs of electrons Count the total number of e- 5) Count the total number of e- used through step 4 and compare to the number calculated in 12CHEM 121 Winter 15

a) CH 3 OH 4. Circle the correct Lewis structure for following compounds: 13CHEM 121 Winter 15

Electronegativities of Elements Electronegativity The ability of one atom in a molecule to attract electrons to itself. H-O-H 14CHEM 121 Winter 15

Classify following bonds nonpolar-covalent, polar-covalent or ionic bonds N-H 3.0 and 2.1 = 0.9 O-H 3.5 and 2.1 = 1.4 C-H 2.5 and 2.1 = 0.4 C-F 2.5 and 4.0 = 1.5 Na-Cl 0.9 and 3.0 = 2.1 Al-Cl 1.5 and 3.0 = 1.5 Pure Covalent: Polar Covalent: Ionic Bond: <1.5 15CHEM 121 Winter 15

5. Circle the most polar bond in the following molecule : 16CHEM 121 Winter 15

Classifying Organic Compounds (hydrocarbon derivatives) Examples Functional Group Ending HydrocarbonsC and H only -ane Alcohols OH R-OH -ol Haloalkanes Cl R-Cl -halide(chloride) Ethers O-R’ R-O-R’ -ether Acids COOH R-COOH -oic acid Amines NH 2 R-NH 2 -amine Ketones C=O R(C=O)R’ -one Aldehydes CHO R-CHO -al 17CHEM 121 Winter 15

Types of formula for organic compounds Chemical formula: Indicate the kind and number of each type of atom in the molecule. Condensed formula: Shows skeletal atoms in a molecule and places them in a sequential order that indicates bonding. Condensed Structural formula: Shows each atom and bonds in a molecule. Expanded Structural formula: Shows each atom and bonds in a molecule. Line-angle formula: The hydrogen atoms are removed from carbon chains, leaving just a carbon line skeleton with functional groups attached to it. Slide - 18CHEM 121 Winter 15

Acyclic Alkanes Are saturated hydrocarbons: Noncyclic alkanes: Noncyclic alkanes: General molecular formula, C n H 2n+2 Structural formula: Normal alkanes n-alkane Normal alkanes n-alkane 19CHEM 121 Winter 15

6. Name the functional group in each of the following molecules 20CHEM 121 Winter 15

7) Give the formulas for each of the following: a) i) Molecular formula: ii) Condensed formula: 21CHEM 121 Winter 15

7) Give the formulas for each of the following: b) i) Molecular formula: ii) Condensed formula: iii) Line-angle formula: b)b 22CHEM 121 Winter 15

8) Give the following for an straight alkane with five carbons atoms i) Molecular formula: ii) Condensed formula: iii) Line-angel formula: iv) IUPAC name: 23CHEM 121 Winter 15

24 General molecular formula: C n H 2n+2 All bond angles about tetrahedral carbon are approximately 109.5° Nomenclature: Unbranched or straight chain alkanes CHEM 121 Winter 15

Nomenclature: Unbranched or straight chain alkanes General molecular formula: C n H 2n+2 All bond angles about tetrahedral carbon are approximately 109.5° 25CHEM 121 Winter 15

Rules of IUPAC Nomenclature of Branched Alkanes Parent name: the longest carbon chain Substituent: a group bonded to the parent chain Alkyl group: a substituent derived by removal of a hydrogen from an alkane; given the symbol R- written in alphabetical order CH 4 becomes CH 3 - (methyl) CH 3 CH 3 becomes CH 3 CH 2 - (ethyl) Prefixes: di-, tri-, tetra-, etc. are not included in alphabetization 26CHEM 121 Winter 15

Naming Branched Alkanes Parent name: the longest carbon chain Substituent: a group bonded to the parent chain Alkyl group: a substituent derived by removal of a hydrogen from an alkane; given the symbol R- written in alphabetical order 27CHEM 121 Winter 15

Common alkyl groups 28CHEM 121 Winter 15 Primary H: hydrogen attached to C atom which is attached to one carbon atoms Secondary H: hydrogen attached to C atom which is attached to two carbon atoms Tertiary H: hydrogen attached to C atom which is attached to three carbon atoms

Common alkyl groups 29CHEM 121 Winter 15

9) IUPAC name of the following branched alkane: 30CHEM 121 Winter 15

10) Give the names of following alkyl groups: 31CHEM 121 Winter 15