1. Biochemistry Study of chemical composition and reactions occurring in living matter Inorganic Compounds Do not contain carbon Exceptions - CO 2, CO, bicarbonates Water is the most abundant and important inorganic material, making up 60% - 80% of all cells and 2/3 of body weight

2. Properties Organic (Benzene) –Low melting pts –Low boiling pts –Low solubility in water –Highly flammable –Covalent bonds Inorganic (NaCl) –High melting pts –High boiling pts –Soluble in water –Nonflammable –Ionic bonds

3. –Carbon: normally forms four covalent bonds and has no unshared pairs of electrons. –Hydrogen: forms one covalent bond and no unshared pairs of electrons. –Nitrogen: normally forms three covalent bonds and has one unshared pair of electrons. –Oxygen: normally forms two covalent bonds and has two unshared pairs of electrons. –Halogen: normally forms one covalent bond and has three unshared pairs of electrons. C H N O =...... Cl......

4. Organic chemistry Organic chemistry is the chemistry of carbon. The name “organic” reflect the fact that organic molecules are derived from living organisms. Four families of organic molecules that are grouped together as the hydrocarbons. Some functional groups that define some of the other families of organic molecules.

5. Single bonds: formed when one pair of electrons is shared between two carbon atoms. Double bonds: involve the sharing of two pairs of electrons. Triple bonds: The sharing of three pairs of electrons. Unsaturated carbon compound: when multiple bonds occur between carbon atoms. Saturated carbon compound: when there are only single bonds between the carbon atoms. Functional group: an atom or group of atoms that can be attached to the carbon atoms. Some terms in organic chemistry

6. Structural formula: shows the orientation of the atoms in either two or three dimensions. Condensed structural formula: used to save space and are written in terms of carbon units. Molecular formula: gives the numbers of each type of atom in the molecule. (i.e. Butane’s molecular formula: C 4 H 10.

7. Writing formulas... Condensed: CH 3 CH(CH 3 )CH = CHCH(CH 3 )CH 3 Kekule’ Skeletal

8. Another common way to abbreviate structure in organic compounds includes the following:

9. Hydrocarbon: The most common organic compound and contains just hydrogen and carbon.

10. HydrocarbonsHydrocarbons AromaticAromaticAliphaticAliphatic

11. HydrocarbonsHydrocarbons AromaticAromaticAliphaticAliphatic AlkanesAlkanes AlkynesAlkynes AlkenesAlkenes

12. HydrocarbonsHydrocarbons AliphaticAliphatic AlkanesAlkanes Alkanes are hydrocarbons in which all of the bonds are single bonds. C C H H H HHH

13. Alkanes Alkanes are hydrocarbons that contain only single bonds. Alkanes are said to be saturated hydrocarbons –Because their hydrogen content is at a maximum. Alkane general formula  C n H 2n + 2 The names of alkanes all end in “-ane.” Methane  butane are gases Pentane  C 17 H 36 are liquids C 18 H 38 and higher are solids

14. Naming and Types of Hydrocarbon Compounds Alkanes: Prefixes for the Number of Carbon Atoms Number of CarbonsPrefix 1Meth 2Eth 3Prop 4But 5Pent 6Hex 7Hept 8Oct 9Non 10Dec

15. IUPAC Nomenclature Set up this rules. International Union of Pure and Applied Chemistry Geneva, Switzerland 1892 IUPAC System of Nomenclature

16. IUPAC Rules 1. Name the longest chain in the parent compound. End in –ane. (Root name) –Number each parent carbon 2. Note the alkyl groups attached 3. Number the carbon that the group is attached to. –Must use the lowest number possible.

17. IUPAC Rules parent compound

18. Give the name of: CH 3  CH 3 ─CH─CH 2 ─CH 3 STEP 1 Longest chain is butane. STEP 2 Number chain. CH 3  CH 3 ─CH─CH─CH 3 1 2 3 4 STEP 3 Locate substituents and name. 2-Methylbutane

19. Give the name of: CH 3 CH 3  CH 3 ─CH─CH─CH 3 STEP 1 Longest chain is butane. STEP 2 Number chain. CH 3 CH 3  CH 3 ─CH─CH─CH 3 1 2 3 4 STEP 3 Locate substituents and name. 2,3-dimethylbutane

20. STEP 1 Longest chain is pentane. STEP 2 Number chain from end nearest substituent. Cl CH 3  CH 3 ─CH 2 ─CH─CH─CH 3 5 4 3 2 1 STEP 3 Locate substituents and name alphabetically. 3-chloro-2-methylpentane Cl CH 3  CH 3 ─CH 2 ─CH─CH─CH 3

21. CH 3 CH 3 | | CH 3 ─CH─CH 2 ─CH ─CH 2 ─CH 3 2,4-dimethylhexane 1 2 3 4 5 6 Cl CH 3 | | CH 3 ─CH 2 ─CH─CH 2 ─C─CH 2 ─CH 3 | Cl 7 6 5 4 3 2 1 3,6-dichloro-3-methylheptane

22. IUPAC Rules Con’t 4. Use prefixes to indicate the amount of attached groups 5. If there are more than two or more different substituents, list them in alphabetical order. If at equal points, lower alphabetical order given lowest number. 6. Prefixes not included in alphabetizing

23. Name each of the following

24. A. B. C. D.

25. Give the IUPAC name for each of the following compounds

26. Practice...write skeletal and condensed formulas. 2,3-dimethylhexane 2-ethyl-3-methylpentane 4-ethyl-3,5-dimethylnonane 4-methylheptane 2,3-dimethylpentane

27. Alkyl Group Alkyl group contains one less hydrogen than the corresponding alkane. In naming this group the “-ane” is dropped and “-yl” is added. For example, methane becomes methyl. Ethane becomes ethyl.

28. Alkyl Group This group does not exist independently but occurs bonded to another atom or molecule.

29. Cycloalkanes Carbon atoms that are joined in a ring or circle. Members of the cycloalkane group possess rings of carbon atoms. They have the general formula C n H 2n. Each carbon atom is bonded to a total of four carbon or hydrogen atoms. The smallest possible ring consists of cyclopropane, C 3 H 6.

30. Cyclic Hydrocarbons The prefix cyclo is used to distinguish a ring structure. Cyclohexane would consist of six singly- bonded carbon atoms in a ring structure. Cyclohexene would consist of six atoms with one double bond in a ring structure. Cyclohexyne would consist of six carbon atoms with one triple bond in a ring structure.

31. The First Four Cycloalkanes Note that in the condensed structural formulas, there is a carbon atom at each corner and enough hydrogens are assumed to be attached to give a total of four single bonds.

32. Answers In cycloalkanes cyclo group is the parent compound of the molecule.

33. Draw these structures Cyclopentane 1-ethyl-2-methylcyclopentane 1-ethyl-1,2,5,5-tetramethylcycloheptane

34. HydrocarbonsHydrocarbons AliphaticAliphatic AlkenesAlkenes Alkenes are hydrocarbons that contain a carbon- carbon double bond. C C H H HH

35. Alkenes Members of the alkene group have a double bond between two carbon atoms. One hydrogen atom has been removed from two adjacent carbon atoms, thereby allowing the two adjacent carbon atoms to form a double bond. General formula is C n H 2n Begins with ethene (ethylene) C 2 H 4 Section 14.3

36. Give the location for double and triple bond parent compound

37. IUPAC Rules 1.Name the longest chain. 2.Indicate the position of the double bond with the lowest number possible. 3.Substituent groups named like alkanes 5-methyl-2-hexene

38. CH 2 = CH ─ CH 2 ─ CH 3 1-butene CH 3 ─ CH=CH ─ CH 2 ─ CH 3 2-pentene CH 3 | CH 3 ─ CH 2 ─ CH=C─CH 3 3-methyl-2-pentene CH 3 ─ C=C ─ CH 2 ─ CH 2 ─ CH 3 2-hexene Naming Alkenes 1 2 3 4 1 2 3 4 5 5 4 3 2 1 1 2 3 4 5 6

39. CH 3 CH 3 ─ CH 2 ─ C=CH ─ CH 3 3-methyl-2-pentene CH 3 ─ CH 2 ─ C=CH ─ CH 3 3-ethyl-2-pentene CH 2 – CH 3 Naming Alkenes 54321 54321

40. Name each of the following

41. Answers 6-dimethyl-2-heptene 2-ethyl-1-butene 4-ethyl-2-methyl-2-hexene 1-methylcyclohexene 2,4,4-trimethyl-2-pentene

42. HydrocarbonsHydrocarbons AliphaticAliphatic AlkynesAlkynes Alkynes are hydrocarbons that contain a carbon- carbon triple bond. HCCH

43. Alkynes Members of the alkyne group have a triple bond between two carbon atoms. Two hydrogen atoms have been removed from each of two adjacent carbon atoms, thereby allowing the two adjacent carbon atoms to form a triple bond. General formula is C n H 2n-2 Begins with ethyne (acetylene) C 2 H 2 Section 14.3

44. Alkynes Carbon atoms share 3 pairs of electrons, forming a triple bond Acetylene Alkynes have similar properties to those of alkanes and alkenes Naming is the same, except they end in -yne

46. HydrocarbonsHydrocarbons AromaticAromatic The most common aromatic hydrocarbons are those that contain a benzene ring. H H H HHH

47. Aromatic Compounds Benzene Named because thought to have strong aroma Now define as anything that has a benzene ring Aliphatic compounds—nonaromatic

48. Aromatic Compounds Benzene is a flat molecule, with all C and H atoms lying in the same plane (coplanar atoms). It is also very symmetrical, with each C atom lying at the angle of a regular hexagon. Thus, every bond angle is 120 degrees. Each bond orbital is cylindrically symmetrical about the line joining the atomic nuclei. These structure are designated with sigma bonds.

49. Aromatic Compounds Each C atom has a fourth orbital, a p orbital. This p orbital consists of two equal lobes - one lying above and one lying below the plane of the other three orbitals (i.e. above and below the plane of the ring). This orbital is occupied by a single electron.

50. Aromatic Compounds The p orbital of any one C atom overlaps equally well the p orbitals of both C atoms to which it is bonded. The result is two continuous electron clouds, one lying above and one lying below the plane of the atoms.

51. Naming One substituent…easy

52. Naming 2 substituents…2 different ways One way…same as before Other way…uses the terms ortho, meta, and para –Ortho (1,2 distribution) –Meta (1,3 distribution) –Para (1,4 distribution)

53. Examples

55. Polycyclic Aromatic Hydrocarbons (PAH) PAHs consist of two or more benzene rings which form a planar structure. They are formed from the incomplete combustion of other hydrocarbons.

56. Aryl Groups Sometimes Benzene rings attach to alkanes or alkenes Known as aryl groups Most common one is phenyl