1. Chapter 9 Organic Chemistry

2. Some Definitions Hydrocarbon Saturated hydrocarbon Unsaturated hydrocarbon Cyclic hydrocarbon Structural formula Condensed structural formula Isomer Functional Group

3. General Uses of Hydrocarbons Halogenated –CFCs –Teflon –Perfluoro Solvents Anesthetics Perfumes, flavorings Building blocks of the body Source: http://www.worldofmolecules.com/pesticides/ddt.htm Teflon: polytetrafluoroethane (PTFE)

4. Alkanes Hydrocarbons that contain only single bonds General formula C n H 2n+2 Named from the number of carbons Can have isomers Can be cyclic (different formula)

5. Properties of Alkanes State of matter –Less than 5 carbons = gas –Between 5 and 16 carbons = liquid –Greater than 16 carbons = solid Non-polar molecules (insoluble in water) Very flammable: used for combustion Physiological effects: dissolve fats, can act as emollients

6. Functional Groups Any variation on the single carbon chain Hydrocarbon stem called an alkyl group Additions of bonds, halogens, oxygen or nitrogen –Alkene –Alkyne –Alcohol –Carboxylic Acid –Ester –Amine –Amide

7. Functional Groups

8. Alkenes Hydrocarbons that contain at least one double bond General formula C n H 2n Named from the number of carbons Can be cyclic –A–Aromatic hydrocarbons: benzene

9. Alkynes Hydrocarbons that contain at least one triple bond General formula C n H 2n-2 Named from the number of carbons

10. Properties of Alkenes & Alkynes State of matter –Contain 2-4 carbons = gas –Contain 5-18 carbons = liquid –Greater than 18 carbons = solid Non-polar molecules (insoluble in water) Flammable Undergo saturation and addition reactions Physiological effects: unsaturated fats, aromatics act as narcotics, many toxic (DDT, phosgene) Source: http://www.worldofmolecules.com/pesticides/ddt.htm DDT

11. Alcohols Alkanes that contain an –OH substituted for any hydrogen –Called a hydroxyl functional group Named according to number of carbons in alkyl group -e on alkane name changes to -ol

12. Properties of Alcohols State of matter –Liquid Soluble in water Formed by fermentation or catalyzed chemical reactions Many are toxic! Other common alcohols: –Propylene glycol: antifreeze –Glycerol: moisturizer, food additive for moisture Source: http://www.worldofmolecules.com/pesticides/ddt.htm Source: http://www.sonarestaurant.com/wine.php

13. Carboxylic Acids Called a carboxyl group May see it written as --COOH Named from the number of carbons + “oic acid” –M–Methanoic acid (in ant and bee stings) –E–Ethanoic acid (acetic acid in vinegar) –P–Propanoic acid –B–Butanoic acid (rancid butter, body odor)

14. Properties of Carboxylic Acids Weak acids Sour taste, neutralize base Produce H + ions in water Carboxylic acid salts = used as anti-mold food additives

15. Esters Contain a carbon double-bonded to one oxygen, single bonded to another Named according to number of carbons 2 words, end in –ate Methyl Butyrate Source: http://www.iff.com/Ingredients.nsf/0/73944D7BC97392548525699F006C522BSource: http://leonlab.bio.uci.edu/images/2D/ethylbutyrate.gif Ethyl Butyrate

16. Properties of Esters Formed by combination of an alcohol and an acid Some soluble in water, some insoluble Fragrant: used in foods and perfumes –Many fruity Other important esters: –Salicylic acid Antipyretic Analgesic Blood thinner Source: http://www.worldofmolecules.com/pesticides/ddt.htm

17. Amines Contain at least one –N group –Called an amino functional group Named according to number of carbons attached to the amino –Names depend on where amino is in chain Name examples: –CH 3 NH 2 = methylamine –CH 3 CH 2 NH 2 = ethylamine –CH 3 NHCH 3 = dimethylamine –CH 3 CH 2 CH 2 NH 2 = propylamine –CH 3 NHCH 2 CH 3 = methylethylamine –CH 3 CH 2 NHCH 3 = ethylmethylamine

18. Properties of Amines Formed from ammonia by replacing hydrogens with alkyl groups Soluble in water (low MW) Many are toxic & carcinogenic Unpleasant odors Act as weak bases Biological importance –Amino acids –Proteins –Drugs Source: http://www.worldofmolecules.com/pesticides/ddt.htm Adrenaline

19. Complex Amines: Heterocyclic Carbon rings with nitrogens replacing carbons Hetero = not evenly spaced Source: http://www.worldofmolecules.com/pesticides/ddt.htm Purine Pyrimidine

20. Amides Contain a carbon double-bonded to oxygen, single bonded to nitrogen Soluble in water (low MW) High boiling points and melting points Most (more than 1 carbon) are solid at room temperature Most important amides are complex –Proteins –Nylon, wool, silk Nylon = hydrocarbons with amide linkages Source: http://www.worldofmolecules.com/pesticides/ddt.htm

21. Try It! Category? Properties? Are isomers possible? Name? CC HH HH HH C H H

22. Try It! Category? Properties? CCN HH HH HHH

23. Try It! Category? Properties? Name? CC HO H H O H

24. Of our 8 molecule types, can you… Name the 3 types of hydrocarbons? Name the hydrocarbon with a triple bond? Name the molecules that include any double bonds? Name the molecules that include any nitrogens? Name the molecules that include any oxygens? Name the molecules that are soluble in water? Name the molecules that are insoluble in water?

25. Practice 1.Which of the molecules below: –Are soluble in water? –Are saturated hydrocarbons? –Are isomers of each other? 2.Name each molecule.

26. Practice 3.Draw a molecule that contains 4 carbons single bonded to each other, and one amine group. Hydrogens make up the rest of the bonds. –Name 2 physical properties of this molecule. 4.Draw a molecule of propene. –Name 3 physical properties of this molecule.

27. Practice 5.Which of the molecules below: –Are insoluble in water? –Are unsaturated hydrocarbons? –Are hydrocarbons that are liquid at room temperature?

28. Practice 6.Draw a molecule that contains 5 carbons single-bonded to each other and one hydroxyl group. Hydrogens make up the rest of the bonds. –Name this molecule –Name 2 physical properties of this molecule. 7.Draw a molecule of pentyne. –Name 3 physical properties of this molecule.

29. Practice 6.Draw a molecule that contains 5 carbons and one ester group. Hydrogens make up the rest of the bonds. –Name 2 physical properties of this molecule. 7.Draw a molecule of pentyne. –Name 3 physical properties of this molecule. 8.Write the molecular formula and name of an alkene that contains 18 hydrogens.

30. Practice CC HH HOH HH CCC HHH HH HHH C H H CC HH HH H CH H H C H H CCN HO HH HH COC OH HH H AB C D E