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

CHAPTER 14 Oxygen, Halogens, & Sulfur General, Organic, & Biological Chemistry Janice Gorzynski Smith

CHAPTER 14: Oxygen, Halogen, & Sulfur 3 Smith. General Organic & Biolocial Chemistry 2nd Ed. 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

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

Alcohols & Alkyl Halides 1°, 2°, 3°

Nomenclature Alcohols 6 # Greek Root Straight Chain Alkane Name 1meth methane 2eth ethane 3prop propane 4but butane 5pent pentane 6hex hexane 7hept heptane 8oct octane 9non nonane 10dec decane # CarbonsStructure Alkyl Group Name 1CH3-methyl 2CH3CH2-ethyl 3CH3CH2CH2-propyl 4CH3CH2CH2CH2-butyl 5CH3CH2CH2CH2CH2-pentyl 6CH3CH2CH2CH2CH2CH2-hexyl Smith. General Organic & Biolocial Chemistry 2nd Ed. parentsuffixprefix ++ parent suffix First give location and type of substituents Second give location of double bond How many carbons in longest chain? How many of the functional group and what is it? Alcohol = “ol” hexan ol 2-methyl 4- *Note: after the greek root of the parent use “an”, ie hexan * Second Note: when we have more then 1 multiple bond the parent name has an “a” after the greek root: hexa OH

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

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

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.

Rxns of Alcohols Alcohol Metabolism Find notes from arthur’s explaination

Nomenclature Ethers 11 # Greek Root Straight Chain Alkane Name 1meth methane 2eth ethane 3prop propane 4but butane 5pent pentane 6hex hexane 7hept heptane 8oct octane 9non nonane 10dec decane # CarbonsStructure Alkyl Group Name 1CH3-methyl 2CH3CH2-ethyl 3CH3CH2CH2-propyl 4CH3CH2CH2CH2-butyl 5CH3CH2CH2CH2CH2-pentyl 6CH3CH2CH2CH2CH2CH2-hexyl Smith. General Organic & Biolocial Chemistry 2nd Ed. parentsuffixprefix ++ parent suffix Use alkyl substitutant naming roots, but drop the “yl” and use “oxy” for the simplest alkyl group bonded to the ether oxygen. How many carbons in longest chain? Use alkane ending: ane but ane 2-ethoxy O

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

Nomenclature Thiols 13 # Greek Root Straight Chain Alkane Name 1meth methane 2eth ethane 3prop propane 4but butane 5pent pentane 6hex hexane 7hept heptane 8oct octane 9non nonane 10dec decane # CarbonsStructure Alkyl Group Name 1CH3-methyl 2CH3CH2-ethyl 3CH3CH2CH2-propyl 4CH3CH2CH2CH2-butyl 5CH3CH2CH2CH2CH2-pentyl 6CH3CH2CH2CH2CH2CH2-hexyl Smith. General Organic & Biolocial Chemistry 2nd Ed. parentsuffixprefix ++ parent suffix Give location and type of substituents, then give location of thiol group. How many carbons in longest chain? Hydrocarbon functional group suffix + “thiol” hept anethiol 2,4-dimethyl 1- SH

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

Rxns of Thiols Oxidation & Reduction

Nomenclature Alkyl Halides 16 # Greek Root Straight Chain Alkane Name 1meth methane 2eth ethane 3prop propane 4but butane 5pent pentane 6hex hexane 7hept heptane 8oct octane 9non nonane 10dec decane # CarbonsStructure Alkyl Group Name 1CH3-methyl 2CH3CH2-ethyl 3CH3CH2CH2-propyl 4CH3CH2CH2CH2-butyl 5CH3CH2CH2CH2CH2-pentyl 6CH3CH2CH2CH2CH2CH2-hexyl Smith. General Organic & Biolocial Chemistry 2nd Ed. parentsuffixprefix ++ parent suffix Give location and type of substituents. Replace “ine” in halide name with “o”, ie Chlorine = chloro How many carbons in longest chain? What is the hydrocarbon functional group? If alkane then “ane” suffix hex ane 2-chloro 4-methyl Cl 6

Functional Groups Alkyl Halides

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 (RNH 2 ). Common Nucleophiles: NaOH ( OH - ), NH 3, RS -, I -.

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

Rxns of Alkyl Halides Substitution Reactions