Organic Chemistry

1. Organic Chemistry The study of Carbon and its compounds

2. ORGANIC CHEMISTRY • The study of compounds containing Carbon atoms. • Carbon has 4 valence electrons, always draw it with 4 covalent bonds around it. • When it forms all single bonds the shape of around the carbon is TETRAHEDRAL.

3. Properties • Solubility • Most nonpolar (like dissolves like) • Most compounds are insoluble in water • Soluble in non-polar solvents O H O

4. Properties • Most are non-electrolytes • Covalent, no conductivity • (an exception is organic acids)

5. Properties • Low Melting/ Boiling Points

6. Properties • Rate of Reaction • Slower than inorganic compounds • High activation energy

7. Properties • Bonding • Nonpolar covalent • Carbon has 4 valance electrons- tetrahedron • Carbon can bond with itself indefinitely (in dif. shapes, many variations) Always make 4 bonds C

8. HYDROCARBONS • Compounds containing only C and H. • 3 open chain families • ALKANES • ALKENES • ALKYNES

9. Homologous Series or families Group of related compounds in which each member differs from the next by one carbon and 2 hydrogens

10. Alkanes • Single-bonded hydrocarbons • Hydrocarbon= only carbon and hydrogen atoms IUPAC nameMolecular FormulaGeneric Formula methane CH4 ethane C2H6 propane C3H8 butane C4H10 pentane C5H12 hexane C6H14 CnH2n+2 heptane C7H16 octane C8H18 nonane C9H20 decane C10H22 • As the molecular size and dispersion forces increase, the boiling point and freezing point increase

11. Table Q

13. Alkenes • have one Double-bonded hydrocarbon • Unsaturated • Same prefix as alkanes, with suffix -ene Dienes contain TWO double bonds, and are not alkenes!

14. Alkynes • one Triple-bonded hydrocarbon • Unsaturated • Same prefix as alkanes, and alkenes, with suffix -yne

15. Saturated vs Unsaturated compounds Single Bonds Double/Triple Bonds

16. Cyclic Hydrocarbons • Benzene • 6 carbon atoms in a ring Aromatic Hydrocarbon Only structure really needs to be known for the regents.

17. June 2 • How to draw and name different organic compounds? • ISOMERS • HW : Read Wkbk pg 194-197 #’s 1 TO 18

18. Isomers Although these structures look different, they both have the same molecular formula of C4 H10 • Compounds with: • the same molecular formulas • different structural formulas C4 H10 Normal Butane 2-Methyl Propane

19. ISOMERS • Same molecular formula but different structural formula. Have different chemical and physical properties.

20. Alkyl Groups • Have 1 less hydrogen (H) than the corresponding alkane • Ex: • Methyl CH3 • 1 less H than CH4 • Ethyl C2H5 • 1 less H than C2H6 3-ethylpentane 2-Methyl Propane

21. Rules for naming organic compounds For Straight or continuous chains: normal form n-alkanes. For branched compounds: 1.Find the longest continuous chain and name the compound. Branches are alkyl groups and end with –yl. 2. The location of the alkyl group is determined by assigning numbers to the carbon atoms of the longest chain, beginning at the end that will give the lowest number to the carbon that contains the alkyl or special group.

22. Drawing Rules It’s as easy as 1, 2, 3…. Step 1 Step 2 Step 3 -ane, Alkane: draw all single bonds -ene, Alkene: draw all single bonds except draw a double on the number carbon that is present in the name -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that is present in the name Make sure all carbons have 4 bonds

23. Draw Hexane Draw Hexane Condensed Formula: CH3-CH2-CH2-CH2-CH2-CH3 1st Task: Hexane -ane = only single bonds Hexane CCCCCC

24. Draw 1-Pentene -ane, Alkane: draw all single bonds -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows 2nd Task: -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows 1 2 3 4 5 5 4 3 2 1

25. Draw 2-butyne -ane, Alkane: draw all single bonds -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows 3rd Task: -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows 1 2 3 4

26. Draw: 2, 3-dimethylbutane

27. Practice Problems • Using Table Q, what type of homologous structure is this and why? • Why? • General formula • Structure • Name

28. June 4 • Objective : Functional groups . • How to distinguish them and what do they do to an organic compound? • Table R • HW P 201-204 #’s 34 TO 48

29. Table R Organic compounds and their functional groups

31. Halides (Halocarbons) • A halide is formed when one or more halogen elements attach themselves to a chain of carbons atoms • Halogen include all the elements in group 17

32. Naming Halocarbons • Halocarbons are usually formed from Alkenes • This is because the double bonds that are present break; leaving empty bonds on the carbons where the halogens are now able to form H H H H C C C H H Double Bond

33. Naming Halocarbons • Every halogen has its own prefix to put at the beginning of its name • It is listed in Table R • When the bonds brake;the halogens fill the empty space 1,2-DiFluoropropane H H H H C C C H H F F

35. Alcohols • Contain 1 less Hydrogen and in its place there is an –OH group instead. • Even though alcohols have an –OH group, they are not considered a base. • This is because there are covalent bonds holding the –OH to the carbons and bases don’t have covalent bonds present on the –OH. • When in solution, acids only release an H+ and bases release OH- H H H C C H H H O H

36. Naming Alcohols • You start with Alkane. (In this case, Methane) • Take away one of the Hydrogen atoms. • Add an –OH group to the empty space • For the name; drop the –e at the end of the prefix (Methane) and add –ol to name the Alcohol! H H Methanol H C C H H H O H

38. Ether • In an ether, there is always an oxygen atom in between two carbons. • And there can be any number of carbons on each side of the oxygen. H H H H C C O C H H H

39. Naming Ethers • Count the amount of carbons on the left side of the Oxygen first. • Count the number of carbons on the right side of the oxygen. • The carbons on the left make Methyl and the carbons on the right make Ethyl, then put Ether at the end. H H H H C C O C H Methyl Ethyl Ether H H H

41. Aldehyde • Aldehydes are known when there is one double bonded oxygen atom at the beginning or the end of a carbon chain. H H H O H C C C C H H H H

42. Forming Aldehydes • Start with a carbon chain (butane). • Drop off two Hydrogen atoms. • Add a double bonded oxygen to the open carbon. H H O H H H H C C C C H H H H

43. Name It! • Four Carbons = butane • Since all aldehydes end in –al. Drop the –e and add –al to the end. Butanal H H O H H C C C C H H H H

45. Ketone • Ketones can be identified by the oxygen double bonded to a carbon in the middle of a carbon chain. H O H H H C C C H C H H H

46. Name a Ketone • We have a chain of carbons (4=butane) • If the double bonded oxygen is found in the middle of a carbon chain then it is a ketone and the –e must be dropped and add –one in its place Butan one e H O H H H C C C H C H H H

48. Organic Acids!!!!!! • Contains a double bonded oxygen and an –OH to the last carbon in the chain • Called acids because H+ ions are released when dissolved in water • Since ions are present when dissolved, an electric current can be conducted through the water • Organic acids are electrolytes! H O H H C C C O H H H

49. Name the acid Form the Acid Start with the carbon chain REMOVE: -e • Hexane Drop off the three hydrogen atoms at the end of the chain ADD: -oic Acid Hexan oic Acid e Add a double bonded oxygen atom and an –OH group to the open carbon atom AND THERE YOU HAVE IT!! O H H H H H H C C H H C C C C H H H H H H O H