CHM 234|Alcohol (cont.) and Ethers and Epoxides
CHM 234|Alcohol (cont.) and Ethers and Epoxides CHM 234
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This 8 page Class Notes was uploaded by Alvin Notetaker on Saturday February 20, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 17 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.
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Date Created: 02/20/16
Alcohol Oxidation of Alcohol Increase CZ bonds Decrease CH bonds Primary alcohol ● Strong oxidation reagent will not stop at aldehyde. ● 2 α−H ● Produce a carboxylic acid group Secondary alcohol ● Strong or mild oxidation reagent will stop and produketone group. ● 1 α−H Tertiary alcohol ● Does not do anything to the molecule. ● 0 α−H Strong oxidation agent:2O4 ● CrO 3with an acid and acetone ● Na 2 2 7ith 2O4and water (mostly used) Mild oxidation agent: pyridinium chlorochromate (PCC) ● PCC with CH 2 2 ● Used to stop ataldehyde. Summary NaCrO / HSO PCC / CH Cl 2 2 7 2 4 2 2 1° alcohol Acid Ketone 2° alcohol Ketone Ketone 3° alcohol None None Example: Oxidation of Phenol Phenol still under oxidation even though it does not have an alpha hydrogen. Synthesis strategies Look for: ● Change in the carbon skeleton ● Change in the functional group Ethers and Epoxides Introduction to Ethers Two alkyl onded to anxygen atom. Can be alkyl, aryl, or vinyl group Nomenclature of Ethers 1. Name each R group 2. Arrange alphabetically 3. End with “ether” tbutyl methyl ether diethyl ether IUPAC names 1. Parent chain: larger R group 2. Name the smaller R group “alkoxy substituent” 2methoxybutane (E)3chloro1ethoxy2methylbut2ene Structure and Properties of Ethers Bond angle is similar to water and alcohol Hydrogen bond acceptor, not hydrogen bond donator ● Meaning that it can interact with protons like in alcohol, but not with itself. Crown Ether Metal atom are stabilized by ether solvent. Crown ether have a strong attraction toward metal atom. Naming Crown Ether XCrownY ● X Total number of atom in crown ● Y Total number of oxygen atom 12Crown4 Crown Ether in Reaction The fluorine anion is very reactive because the potassium cation bonded itself to the crown ether. ● Crown ether is called h ost. + ● The metal atom, for example, the K ion, is calleguest. Smaller crown binds to smaller cation. Preparation of Ether Prepared by acidcatalyzed dehydration of ethanol ● Symmetrical ether only Mechanism: Williamson Ether Synthesis Mechanism: ● Can be for nonsymmetrical and symmetrical ether ● Halide goes oness hindered alkyl group ● Alkoxide ion goes onmore hindered alkyl group Example: Alkoxymercuration–Demercuration __________________________________________________________________ Review __________________________________________________________________ If alcohol is in the reaction instead of water, than the reaction is a Markovnikov addition of the alcohol. Example: Reactions of Ether Acid cleavage ● Ether is a poor leaving group ● Only HBr and HI can be used because they are strong acid and god nucleophile SN1 or SN reaction are depended on the R group When phenyl ether is under cleavage, it will produce a phenol and an alkyl halide. Neither of the two substitution reaction will work because of the sp2 hybridization . If The R group a secondary carbocation , the reaction will be a S N reaction because it is faster. Nomenclature of Epoxides Cyclic ethers are rings with an oxygen atom Oxirane Oxetane Oxolane Oxane Oxiranes = Epoxides Two ways of naming 1. Oxygen is given the 1position 2. Naming similar to alkane, but an “epoxy” is placed into the name for the carbon bonded to the oxygen. 2ethyloxirane (top) 2,2dimethyloxirane (top) 1,2epoxybutane (bottom) 1,2epoxy2methylpropane
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