Follow Up Questions from Chapter 13: Natural Polymers

1. Follow Up Questions from Chapter 13: Natural Polymers Natural Latex Rubber Natural precursor Industrial precursor Spider Silk Cellulose

2. CHAPTER 14 Oxygen, Halogens, & Sulfur General, Organic, & Biological Chemistry Janice GorzynskiSmith

3. CHAPTER 14: Oxygen, Halogen, & Sulfur • Learning Objectives: • Name organic compounds with carbon-heteroatom single bonds (oxygen, halogens, sulfur) • Identify 1°, 2°, 3° alcohols and alkyl halides • Predict the products or reactants for following reactions: • Alcohol dehydration • Alcohol oxidation • Sulfur oxidation • Sulfur reduction Smith. General Organic & Biolocial Chemistry 2nd Ed.

4. Functional Groups Overview Alkyl halides Alcohols Ethers Thiols Single Bond to a Heteroatom Functional Groups Smith. General Organic & Biolocial Chemistry 2nd Ed.

5. Alcohols & Alkyl Halides 1°, 2°, 3°

6. Nomenclature Alcohols OH 6 4 2 3 5 1 + + prefix parent suffix First give location and type of substituents Second give location of double bond prefix How many carbons in longest chain? parent How many of the functional group and what is it? Alcohol = “ol” suffix 2-methyl 4- hexan ol *Note: after the greek root of the parent use “an”, iehexan * Second Note: when we have more then 1 multiple bond the parent name has an “a” after the greek root: hexa Smith. General Organic & Biolocial Chemistry 2nd Ed.

7. Functional Groups Alcohols Fermentation Smith. General Organic & Biolocial Chemistry 2nd Ed.

8. Rxns of Alcohols Elimination Reaction: Dehydration Zaitsev Rule: The major product in elimination is the alkene that has more alkyl groups bonded to it.

9. Rxns of Alcohols Oxidations Oxidation requires breaking C-H bonds and forming new C-O bonds. When alcohol is the starting material the products always have a carbonyl group.

10. Rxns of Alcohols Alcohol Metabolism Find notes from arthur’sexplaination

11. Nomenclature Ethers 1 4 2 O 3 + + prefix parent suffix Use alkyl substitutant naming roots, but drop the “yl” and use “oxy” for the simplest alkyl group bonded to the ether oxygen. prefix parent How many carbons in longest chain? suffix Use alkane ending: ane 2-ethoxy but ane Smith. General Organic & Biolocial Chemistry 2nd Ed.

12. Functional Groups Ethers Diethyl Ether The first anesthetic administered in 1842 by Crawford Long Heterocycles O Smith. General Organic & Biolocial Chemistry 2nd Ed.

13. Nomenclature Thiols SH 2 4 5 3 1 + + prefix parent suffix Give location and type of substituents, then give location of thiolgroup. prefix How many carbons in longest chain? parent Hydrocarbon functional group suffix + “thiol” suffix 2,4-dimethyl 1- hept anethiol Smith. General Organic & Biolocial Chemistry 2nd Ed.

14. Functional Groups Thiols Insulin Smith. General Organic & Biolocial Chemistry 2nd Ed. Jean-Philippe Cartailler, Ph.D. The Beta Cell Consortium

15. Rxns of Thiols Oxidation & Reduction

16. Nomenclature Alkyl Halides 1 2 6 4 Cl 3 5 + + prefix parent suffix Give location and type of substituents. Replace “ine” in halide name with “o”, ie Chlorine = chloro prefix parent How many carbons in longest chain? What is the hydrocarbon functional group? If alkane then “ane” suffix suffix 2-chloro 4-methyl hex ane Smith. General Organic & Biolocial Chemistry 2nd Ed.

17. Functional Groups Alkyl Halides

18. Rxns of Alkyl Halides Substitution Reactions with Alkyl Halides Substitution Reactions at 1° Carbons Halides (Cl, Br) are good leaving groups (L) because they form very polar covalent bonds with carbon. Nucleophiles (Nu-) include negatively charged molecules or amines (RNH2). Common Nucleophiles: NaOH ( OH-), NH3, RS-, I-.

19. Rxns of Alkyl Halides Substitution Reactions Substitution Reactions at 1° Carbons Substitution Reactions at 3° Carbons

20. Rxns of Alkyl Halides Substitution Reactions