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UH CHEM 3332 - Esters

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CHEM 3332 1st Ediiton Lecture 6Outline of Last Lecture I. Ester FormationA. Fischer Esterfication (intermolecular dehydration) – mechanism this semester!B. Nucelophillic acyl substitution of acid chlorideII. Unique reactions of 1,2 diolsA. Periodic acid cleavage B. Pinacol – Pinacolone RearrangementSpectroscopy ReviewOutline of Current Lecture Chapter 14: Ethers, Epoxides, SulfidesImportance: ether, not a goof synthetic intermediate, it’s an important solvent. Epoxide is excellent synthetic intermediate Structure/ Polarity/ Physical PropertiesEthers as solvents:- Limited reactivity- Not as toxic as chlorinated solvents such as CCl4/ChCl3/CH2CL2- Low boiling, so easily removed- Large diploe moments and H – bond acceptors, so dissolve polar substances- No H- bonds between ether molecules, so dissolve nonpolar substances (no-H bonds to disrupt)- No acidic hydrogens, so can serve as solvents under strong basic conditionsEther Complexes:a. Grignard reagen-b. Boron reagents-c. Crown ether/ cations –Nomenclature of EthersI. Acyclic Ethers – 2 accepted systemsA. As alkyl alkyl ether: Name each alkyl group attached to oxygen in alphabetical order and add “ether” (common name)B. As alkoxy alkane: Name the RO- group as an alkoxy group. The larger or more complexgroup is chosen as the parent name.II. Cyclic ethers (Epoxides) – 3 accepted systemA. Common name: Name of alkene used to form the epoxide plus “oxide”. (industry uses)B. Name the oxygen of the epoxide ring as an epoxy substituent. Use both numbers of the carbons bonded to oxygen to designate position.C. Name as derivative of oxiraneSynthesis of EthersI. Williamson Ether SynthesisThese notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute.II. Alkoxymercuration/demercurationMechanismIII. Symmetrical ethers through intermolecular dehydration of 1 alcohols. – DO NOT USE THIS!!! LIMITED REACTION!Current LectureChapter 14: Ethers (acyclic or cyclic), Epoxides (Ring size 3) Importance: ether, not a goof synthetic intermediate, it’s an important solvent. Epoxide is excellent synthetic intermediate Structure/ Polarity/ Physical PropertiesEthers as solvents:- Limited reactivity- Not as toxic as chlorinated solvents such as CCl4/ChCl3/CH2CL2- Low boiling, so easily removed- Large diploe moments and H – bond acceptors, so dissolve polar substances- No H- bonds between ether molecules, so dissolve nonpolar substances (no-H bonds to disrupt)- No acidic hydrogens, so can serve as solvents under strong basic conditionsEther Complexes:a. Grignard reagent-b. Boron reagents-c. Crown ether/ cations – KF/ 18-crown-6/ CH3CNNomenclature of EthersI. Acyclic Ethers – 2 accepted systemsA. As alkyl alkyl ether: Name each alkyl group attached to oxygen in alphabetical order and add “ether” (common name)B. As alkoxy alkane: Name the RO- group as an alkoxy group. The larger or more complexgroup is chosen as the parent name.II. Cyclic ethers (Epoxides) – 3 accepted systemA. Common name: Name of alkene used to form the epoxide plus “oxide”. (industry uses)B. Name the oxygen of the epoxide ring as an epoxy substituent. Use both numbers of the carbons bonded to oxygen to designate position.C. Name as derivative of oxiraneSynthesis of EthersI. Williamson Ether SynthesisII. Alkoxymercuration/demercurationMechanism:III. Symmetrical ethers through intermolecular dehydration of 1 alcohols. – DO NOT USE THIS!!! LIMITED


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