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CHM 234|Alcohol (cont.) and Ethers and Epoxides

by: Alvin Notetaker

CHM 234|Alcohol (cont.) and Ethers and Epoxides CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Alcohol cont and Ethers and Epoxides
Alvin Notetaker
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Topic: Final section of alcohol introduction to ether and epoxides
General Organic Chemistry II
Class Notes
Organic Chemistry
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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:2​O​4   ● CrO​ 3​with an acid and acetone  ● Na​ 2​ 2​ 7​ith 2​O​4​and water (mostly used)    Mild oxidation agent: pyridinium chlorochromate (P​CC) ​  ● PCC with CH​ 2​ 2  ● Used to ​stop​ ataldehyde.​       Summary      Na​Cr​O​  / 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 an​xygen 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 on​ess 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    SN​1 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 sp​2 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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