2. Chapter 4: Carbon Do Now: How many bonds can carbon form?

3. Carbon (The Backbone of life) Body consists of carbon based compounds (ex: proteins, lipids, carbohydrates, DNA) Carbon can form up to 4 bonds Most frequent partners are O, H, N Carbon chains form the skeleton of most organic molecules

4. Fig. 4-4 Hydrogen (valence = 1) Oxygen (valence = 2) Nitrogen (valence = 3) Carbon (valence = 4) H O N C

5. Organic Chemistry The study of compounds that contain carbon Most contain Hydrogen atoms as well as carbon.

6. Carbon can form 4 covalant bonds with a variety of atoms

7. Hydrocarbons Organic molecules consisting of only carbon and hydrogen Non-polar molecules (fats)

8. Carbon Skeletons

9. Isomers Molecules with same molecular formula but different structures (shapes) –different chemical properties –different biological functions 6 carbons

10. Fig. 4-7 Pentane (a) Structural isomers (b) Geometric isomers 2-methyl butane cis isomer: The two Xs are on the same side. trans isomer: The two Xs are on opposite sides. (c) Enantiomers L isomer D isomer Structural: different covalent arrangement Geometric: same covalent arrangements, different spatial arrangements Enantiomers: isomers that are mirror images

11. Isomers- Form affects function Structural differences create important functional significance –medicines L-version active but not D-version –sometimes with tragic results…

12. Form affects function Thalidomide –prescribed to pregnant women in 50s & 60s –reduced morning sickness, but… –stereoisomer caused severe birth defects

13. Fig. 4-8 Drug Ibuprofen Albuterol Condition Pain; inflammation Asthma Effective Enantiomer S-Ibuprofen R-Albuterol R-Ibuprofen S-Albuterol Ineffective Enantiomer

14. Functional groups Parts of organic molecules that are involved in chemical reactions –give organic molecules distinctive properties hydroxyl amino carbonyl sulfhydryl carboxyl phosphate Affect reactivity –makes hydrocarbons hydrophilic –increase solubility in water

15. Hydroxyl –OH –organic compounds with OH = alcohols –names typically end in -ol ethanol

16. Carbonyl C=O –O double bonded to C if C=O at end molecule = aldehyde if C=O in middle of molecule = ketone

17. Carboxyl –COOH –C double bonded to O & single bonded to OH group compounds with COOH = acids –fatty acids –amino acids

18. Amino -NH 2 –N attached to 2 H compounds with NH 2 = amines –amino acids NH 2 acts as base –ammonia picks up H + from solution

19. Sulfhydryl –SH –S bonded to H compounds with SH = thiols SH groups stabilize the structure of proteins

20. Phosphate –PO 4 –P bound to 4 O connects to C through an O lots of O = lots of negative charge –highly reactive transfers energy between organic molecules –ATP

21. Look at the difference Basic structure of male & female hormones is identical –identical carbon skeleton –attachment of different functional groups –interact with different targets in the body different effects

22. Diversity of molecules Substitute other atoms or groups around the carbon –ethane vs. ethanol H replaced by an hydroxyl group (–OH) nonpolar vs. polar gas vs. liquid biological effects! ethane (C 2 H 6 ) ethanol (C 2 H 5 OH)