ORGANIC CHEMISTRY

1. ORGANIC CHEMISTRY STUDY OF CARBON COMPOUNDS -CONTAINING Chapter 1

2. SHORT HISTORY OF CHEMISTRY PRE-1828 ERA TWO MAJOR DISCIPLINES EMERGING INORGANIC - MINERAL CHEMISTRY ORGANIC CHEMISTRY - PLANTS AND ANIMALS Chapter 1

3. BERZILIUS’ DEFINITIONS ORGANIC COMPOUNDS CHARACTERISTIC PRODUCTS OF LIVING ORGANISMS SUBSTANCES LIKE SUGAR AND OLIVE OIL INORGANIC COMPOUNDS PRODUCTS FROM NON-LIVING ENVIRONMENT SUBSTANCES LIKE WATER AND IRON Chapter 1

4. 1828 Woehler’s urea synthesis Ammonium isocyanate + heat ------> urea NH4CNO NH2CONH2 “I have been able to make urea without aid of kidney of man or dog. 1828 Chapter 1

5. Liszt - Old Chapter 1

6. BIRTHS JULES VERNE - AROUND THE WORLD IN 80 DAYS LEO TOLSTOY - ANNA KORNINA, KREUTZER SONATA HANS CHRISTIAN ANDERSON WANG TAO - CHINESE SELF-STRENGTHENING MOVEMENT AMEER MINAI - INDIAN SONG WRITER - AAHISTAA MARRIAGES BARTHOLOMEW HEIFNER AND POLLY GRISHAM. IN SHELBY COUNTY, ENGLAND Chapter 1

7. Wang Tao Attempted to bring China into the 19th Century Was put to death Chapter 1

8. IMPORTANT EVENTS ANDREW JACKSON ELECTED PRESIDENT OF USA DEFEATED JOHN Q. ADAMS RUSSO-PERSIAN WAR ENDED FATH ‘ALI SHAH’ AND RUSSIAN COUNTERPART SIGNED TURKMANCHAI TREATY GAVE RUSSIA - GEORGIA, ARMENIA, AND AZERBAIJAN Chapter 1

9. Post 1828 • Over 18,000 million compounds have been synthesized • Pharmaceuticals • Biochemicals • Plastics • Agrichemicals • Paints Chapter 1

10. Why so many organic? FORMS COVALENT BONDS WITH NON-METALS H O N P S Se X FORMS COVALENT BONDS WITH MANY METALS Li Mg Al Cd Fe Chapter 1

11. AND WITH ITSELF No limit Chapter 1

12. => Atomic Structure • protons, neutrons, and electrons • isotopes Chapter 1

13. Multiple Bonding => Chapter 1

14. Naming Hydrocarbons(nomenclature)

15. Drawing Structures: It’s All Good 2-butene On a test, choose a method that shows all Hs This is called the “condensed structure” CH3CH=CHCH3 Using brackets can also shorten some formulas: CH3CH2CH2CH2CH2CH3 vs. CH3(CH2)4CH3

16. Basic Naming of Hydrocarbons Hydrocarbon names are based on: 1) type, 2) # of carbons, 3) side chain type and position 1) name will end in -ane, -ene, or -yne 2) the number of carbons is given by a “prefix” 1 meth- 2 eth- 3 prop- 4 but- 5 pent- 6 hex- 7 hept- 8 oct- 9 non- 10 dec- Actually, all end in a, but a is dropped when next to a vowel. E.g. a 6 C alkene is hexene Q - What names would be given to these: 7C, 9C alkane 2C, 4C alkyne 1C, 3C alkene heptane, nonane ethyne, butyne methene, propene

17. Monkeys • Eat • Peeled • Bananas Mnemonic for First Four Prefixes First four prefixes • Meth- • Eth- • Prop- • But-

18. Other Prefixes • Pent- ? Decade Decimal Decathalon • Oct- • Dec- • Hex-, Hept-, Non-

19. C2H4 Numbering Carbons 1-pentene Q- draw pentene A- Where’s the double bond? We # C atoms. • Naming compounds with multiple bonds is more complex than previously indicated. • When 2+ possibilities exist, #s are needed. • Always give double bond the lowest number. • Q - Name these 2-butene ethene 3-nonyne

20. Formal Charge • Formal charge: The charge on an atom in a molecule or a polyatomic ion. • To derive formal charge 1. Write a correct Lewis structure for the molecule or ion. 2. Assign each atom all its unshared (nonbonding) electrons and one-half its shared (bonding) electrons. 3. Compare this number with the number of valence electrons in the neutral, unbonded atom. 4. The sum of all formal charges is equal to the total charge on the molecule or ion.

21. Formal Charge • Example:Draw Lewis structures, and show which atom in each bears the formal charge.

22. Apparent Exceptions to the Octet Rule • Molecules that contain atoms of Group 3A elements, particularly boron and aluminum.

23. Apparent Exceptions to the Octet Rule • Atoms of third-period elements are often drawn with more bonds than allowed by the octet rule. • The P in trimethylphosphine obeys the octet rule by having three bonds and one unshared pair. • A common depiction of phosphoric acid, however, has five bonds to P, which is explained by invoking the use of 3d orbitals to accommodate the additional bonds.

24. Apparent Exceptions to the Octet Rule • However, the use of 3d orbitals for bonding is in debate. • An alternative representation that gives P in phosphoric acid an octet has four bonds and a positive formal charge on P. The oxygen involved in the double bond of the alternative depiction has one bond and a negative formal charge.

25. Apparent Exceptions to the Octet Rule • Sulfur is commonly depicted with varying numbers of bonds. In each of the alternative structures, sulfur obeys the octet rule.

26. Chapter 1 Bonding and Geometry Chem 30A Lecture 2

27. Functional Groups • Functional group: An atom or group of atoms within a molecule that shows a characteristic set of physical and chemical properties. • Functional groups are important for three reasons: 1. Allow us to divide compounds into classes. 2. Each group undergoes characteristic chemical reactions. 3. Provide the basis for naming compounds.

28. Alcohols • Contain an -OH (hydroxyl) group bonded to a tetrahedral carbon atom. • Ethanol may also be written as a condensed structural formula.

29. Alcohols • Alcohols are classified as primary (1°), secondary (2°), or tertiary (3°) depending on the number of carbon atoms bonded to the carbon bearing the -OH group.

30. Alcohols There are two alcohols with molecular formula C3H8O

31. Amines • Contain an amino group; an sp3-hybridized nitrogen bonded to one, two, or three carbon atoms. • An amine may by 1°, 2°, or 3°.

32. Aldehydes and Ketones • Contain a carbonyl (C=O) group.

33. Carboxylic Acids • Contain a carboxyl (-COOH) group.

34. Carboxylic Esters • Ester: A derivative of a carboxylic acid in which the carboxyl hydrogen is replaced by a carbon group.

35. Carboxylic Amide • Carboxylic amide, commonly referred to as an amide: A derivative of a carboxylic acid in which the -OH of the -COOH group is replaced by an amine. • The six atoms of the amide functional group lie in a plane with bond angles of approximately 120°.