1. 1-1 Chemistry 121, Winter 2008, LA Tech Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@chem.latech.edu Office: 311 Carson Taylor Hall ; Phone: 318-257-4941; Office Hours: MTW 9:00 am - 11:00 am; TR 9::00 - !0:00 am & 1:00-2:00 pm. December 19, Test 1 (Chapters 12-14) January 2 Test 1 (Chapters 15-16) February 6 (Chapters 17-19) February 27, (Chapters 20-22) March 2, 2009, Make Up Exam: Bring Scantron Sheet 882-E Chemistry 121(01) Winter 2009

2. 1-2 Chemistry 121, Winter 2008, LA Tech Introduction to Organic and biochemistry Chapter 1-12

3. 1-3 Chemistry 121, Winter 2008, LA Tech Introduction to organic & Biochemistry Test 1 12. Saturated Hydrocarbons 13. Unsaturated Hydrocarbons 14. Alcohols, Phenols, and Ethers Test 3 18. Carbohydrates 19. Lipids 20. Proteins Test 2 15. Aldehydes and Ketones 16. Carboxylic Acids, Esters, and Other Acid Derivatives 17. Amines and Amides Test 4 21. Enzymes and Vitamins 22. Nucleic Acids 23. Biochemical Energy Production Self Study 24. Carbohydrate Metabolism 25. Lipid Metabolism 26. Protein Metabolism

4. 1-4 Chemistry 121, Winter 2008, LA Tech Introduction to organic & Biochemistry 12.1 Organic and Inorganic Compounds 12.2 Bonding Characteristics of the Carbon Atom 12.3 Hydrocarbons and Hydrocarbon Derivatives

5. 1-5 Chemistry 121, Winter 2008, LA Tech Organic and Inorganic compounds Ionic Compounds: Have cations and anions are also called salts made of metlas and non-metals Covalent Compounds: Consists of neutral molecules connected by covalent bonds to non metallic elements. Organic Compounds : have carbon atoms sharing electrons in covalent bonds. Carbon atoms form chains, and many atoms can be joined by covalent bonds. Inorganic Compounds: Consist of ions produced by loss or gain of electrons between a metal and non metal.

6. 1-6 Chemistry 121, Winter 2008, LA Tech Covalent or Ionic Identify covalent and ionic compounds: H 2 O, NaCl, C 2 H 5 OH, CH 3 COOH, Na 2 CO 3, CH 3 OK, KOH Covalent : Ionic:

7. 1-7 Chemistry 121, Winter 2008, LA Tech Organic or Inorganic Identify organic and inorganic compounds: H 2 O, NaCl, C 2 H 5 OH, CH 3 COOH, Na 2 CO 3, C 3 H 8, KOH Organic : Inorganic:

8. 1-8 Chemistry 121, Winter 2008, LA Tech Introduction Organic chemistry is the study of the compounds of carbon with H, N, O and S. Biochemistry is the study of the chemical processes in living organisms. It deals with the structure and function of cellular components.

9. 1-9 Chemistry 121, Winter 2008, LA Tech More details.. Organic vs. Inorganic Organic compounds are produced by living things. Inorganic compounds are produced by non-living naturalprocesses or by human intervention in the laboratory. This was the most common definition of "organic" until Wohler's 1828 synthesis of urea (an organic compound) from ammonium cyanate (a salt, and therefore? Organic/inorganic). But we no longer use this definition, for the simple reason that many compounds that everyone agrees are organic -- including "natural products" which are routinely made by living things -- have been synthesized by humans. Organic compounds contain carbon. Inorganic compounds don't. Inorganic compounds don't. Organic compounds contain carbon-hydrogen bonds. Inorganic compounds don't. Organic compounds contain carbon-hydrogen bonds. Inorganic compounds don't.

10. 1-10 Chemistry 121, Winter 2008, LA Tech Bonding Characteristics of the Carbon Atom C is a small atom it forms four bonds consisting of single, double, and triple carbon to carbon bonds or other atoms it forms four bonds consisting of single, double, and triple carbon to carbon bonds or other atoms Shows tetrahedral (all 4 - ), trigonal planar (2 - & 1 =) and linear ( 1 - & 1  ) Shows tetrahedral (all 4 - ), trigonal planar (2 - & 1 =) and linear ( 1 - & 1  ) it forms strong bonds with C, H, O, N, and some metals it forms strong bonds with C, H, O, N, and some metals form stable covalent bonds to other carbon atoms – catenation: Long carbon chains can be produced. form stable covalent bonds to other carbon atoms – catenation: Long carbon chains can be produced.

11. 1-11 Chemistry 121, Winter 2008, LA Tech Four sp 3 hybrids Four sp 3 hybrids Three sp 2 hybrids Three sp 2 hybrids Two sp hybrids Two sp hybrids s and p hybrids

12. 1-12 Chemistry 121, Winter 2008, LA Tech Hybrid Atomic Orbitals Hybridization is the mixing up of two or more atomic orbitals There are three types of hybrid atomic orbitals for carbon sp 3 sp 3 (one s orbital + three p orbitals give four sp 3 orbitals) sp 2 sp 2 (one s orbital + two p orbitals give three sp 2 orbitals) sp sp (one s orbital + one p orbital give two sp orbitals)

13. 1-13 Chemistry 121, Winter 2008, LA Tech  and  bonds in single and multiple bonds single bond - one shared pair of electrons between two atoms; a  bond double bond - two shared pairs of electrons between two atoms; one s bond and one  bond triple bond - three shared pairs of electrons between two atoms; one s bond and two p bonds

14. 1-14 Chemistry 121, Winter 2008, LA Tech  and  bonds Overlap of hybrid orbitals can form two types of bonds, depending on the geometry of the overlap  bonds  bonds are formed by “direct” overlap  bonds  bonds are formed by “parallel” overlap of unhybrid p prbitlas

15. 1-15 Chemistry 121, Winter 2008, LA Tech Predicting hybridization of atoms in a Lewis structure Count sigma bonds and unshared electrons around the atom If the total number of pairs: 2 sp hybridization 3 sp 2 hybridization 4 sp 3 hybridization

16. 1-16 Chemistry 121, Winter 2008, LA Tech Counting  and  bonds in Lewis structure

17. 1-17 Chemistry 121, Winter 2008, LA Tech Draw Lewis structure of molecules CHCl 3 C 2 H 4 C 3 H 8 O CH 3 CH 2 CH 2 OH CH 3 CH 2 OCH 3 CH 3 CO 2 H CH 3 CHO

18. 1-18 Chemistry 121, Winter 2008, LA Tech Resonance For many molecules and ions with double bonds, two or more Lewis structure could be written

19. 1-19 Chemistry 121, Winter 2008, LA Tech Curved arrow Electron pushing Curved arrow: a symbol used to show the redistribution of valence electrons In using curved arrows, there are only two allowed types of electron redistribution: from a bond to an adjacent atom from an atom to an adjacent bond Electron pushing by the use of curved arrows is also used in explaining reaction mechanisms

20. 1-20 Chemistry 121, Winter 2008, LA Tech Drawing Curved Arrows To show the movement of electrons in breaking and forming bonds. The tail of the arrow is started at the site of electron density (negative character such as a pi bond or lone pair of electrons) and proceeds to the arrowhead which is drawn to the site of electron deficiency (positive character). NEGATIVE TO POSITIVE! Arrows can be drawn from: 1) lone pair bond 2) bond lone pair 3) bond bond

21. 1-21 Chemistry 121, Winter 2008, LA Tech Bond Properties Bond strength: strongest weakest Bond length: longest shortest

22. 1-22 Chemistry 121, Winter 2008, LA Tech Formula Molecular formula kind and number of each type of atoms Structural formula each atom and bond in a molecule

23. 1-23 Chemistry 121, Winter 2008, LA Tech Condensed formula Condensed formula Shorthand way of writing a formula. Lists all atoms in order and tells how they are bound together. Example.Example. Propane C3H8C3H8C3H8C3H8 CH 3 CH 2 CH 3 This is a convenient format for describing a molecule using text.

24. 1-24 Chemistry 121, Winter 2008, LA Tech Structural Formula of hydrocarbons One simple class of compound is the alkane which has only C, H and single bonds. methane ethane propane butane CH 4 CH 3 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 2 CH 3

25. 1-25 Chemistry 121, Winter 2008, LA Tech Line Formula of hydrocarbons One simple class of compound is the alkane which has only C, H and single bonds. methane ethane propane butane CH 4 CH 3 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 2 CH 3

26. 1-26 Chemistry 121, Winter 2008, LA Tech Line formula Similar to structural formula. Each line represents a bond. Carbons are assumed to be present at the end of each line segment. Hydrogen is not shown when bound to carbon. NOHH H 2 C C H 2 C H 2 CH 2 H 2 C H 2 C H 2 C C H 2 C H 2 H 2 C H 2 C H 2 C H 2 C C H 2 C H 2 N H 2 C H 2 C H 2 C C H 2 C H 2 H 2 C H 2 C H 2 C OHOH H H 2 C 3

27. 1-27 Chemistry 121, Winter 2008, LA Tech Models Three dimensional representations Ball and Stick Space Filling Both are models of propane.

28. 1-28 Chemistry 121, Winter 2008, LA Tech Base names of organic compounds Prefix Carbons Meth-1 Eth-2 Prop-3 But-4 Pent-5 Hex-6 Hept-7 Oct-8 Non-9 Dec- 10 I see much memorization in your future!

29. 1-29 Chemistry 121, Winter 2008, LA Tech Functional Groups in Organic Compounds Functional group: an atom or group of atoms within a molecule that shows a characteristic set of physical and chemical properties Functional group divide organic compounds into classes the sites of characteristic chemical reactions the basis for naming organic compounds

30. 1-30 Chemistry 121, Winter 2008, LA Tech Alcohol(carbon, hydrogen and oxygen) CH 3 -CH 2 -OH Thiol (thioalcohol) thio means sulfur CH 3 -CH 2 -SH Amine CH 3 -CH 2 -NH 2 Ether CH 3 -CH 2 -O-CH 2 -CH 3 Common Functional Groups

31. 1-31 Chemistry 121, Winter 2008, LA Tech Carbonyl group or unit Aldehyde ketones Carboxylic acids Common Functional Groups (continued)

32. 1-32 Chemistry 121, Winter 2008, LA Tech Class Functional group Example Classification of organic compounds

33. 1-33 Chemistry 121, Winter 2008, LA Tech IUPAC - a general system: Examples ene prop-en-e = propene anol eth-an-ol = ethanol anone but-an-one = butanone anal but-an-al = butanal anoic acid pent-an-oic acid = pentanoic acid anol cyclohex-an-ol = cyclohexanol yne eth-yn-e = ethyne anamine eth-an-amine = ethanamine en-e cyclo-pent-en-e

34. 1-34 Chemistry 121, Winter 2008, LA Tech The IUPAC system: Naming Organic Compounds As a general system of nomenclature prefix-infix-suffix prefixprefix tells the number of carbon atoms in the parent infixinfix tells the nature of the carbon-carbon bonds suffixsuffix tells the class of compound

35. 1-35 Chemistry 121, Winter 2008, LA Tech Hydrocarbons Composed of only carbon and hydrogen; in petroleum and coal Saturated - hydrocarbons with all C-C single bonds C-C single bonds Unsaturated - hydrocarbons with at least one C-C double bond or triple bonds

36. 1-36 Chemistry 121, Winter 2008, LA Tech Classification of Hydrocarbons

37. 1-37 Chemistry 121, Winter 2008, LA Tech Examples of Alkanes, Alkenes, Alkynes and Arenes : ethaneetheneethyne benzene C 2 H 6 C 2 H 4 C 2 H 2 C 6 H 6 C n H 2n+2 C n H 2n C n H 2n  2 C n H n saturatedunsaturatedunsaturated Aromatic alkanealkenealkyne Arene

38. 1-38 Chemistry 121, Winter 2008, LA Tech Biochemical Principles Structures of Monomers and Polymers found in living systems Carbohydrates (glucose, starch, cellulose) Proteins (amino acids, proteins) Nucleic acids (Nucleotides-A,T,G,C and RNA & DNA) Functions of Biological molecules Enzymes and Vitamins Nucleic Acids and hereditary Biochemical Energy Production Carbohydrate Metabolism Lipid Metabolism Protein Metabolism