Ch. 7 Alcohols and Ethers
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| pKa | pKa=-logKa. strong acids have high Ka's and small pka's. Phenol has small pka so most acidic of alcohols listed
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| how can alcohols be prepared | from the reduction of aldehydes, ketones, carboxylic acids, or esters. Lithium aluminum hydride (LiAlH4 or LAH) and sodium borohydride (NaBH4) two most common reducing reagents
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| how can phenols be synthesized | arylsulfonic acids with hot NaOH. Or hydrolysis of diazonium salts.
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| Reducing agents | Have lots of H's (NaBH4 and LiAlH4), oxidizing agents have lots of O's (KMnO4 and CrO3)
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| oxidation of alcohols | generally involves some form of chromium (VI) as oxidizing agents. PCC is only mild oxidizing agent, partially oxidizes 1^o alcohols to aldehyde
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| Jones's oxidation | chromium trioxide, CrO3 dissolved with dilute sulfuric acid in acetone. oxidized primary alcohols to carboxylic acids and secondary alcohols to ketones
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| treatments of phenols with oxidizing reagents produces what | quinones
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| ethers | do not H bond, boil approx. same temp as alaknes of comparable weight, only slightly polar, and slightly soluble in water. Most inert organic reagent so freq. used as solvents
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| williamson either synthesis | produces ethers from the reaction of metal alkoxides with primary alkyl halides or tosylates
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| epoxide or oxrine formation | oxidation of an alkene with peroxy acid (RCOOOH)
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| peroxides and ether | ethers react with oxygen in air to form highly explosive compounds called peroxides
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| strong bases as leaving group | are poor leaving groups
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| symmetric and asymmetric epoxides | sym. either C can be attacked, asyn. most substituted C nuclophilically attacked when catalyzed with acid, least sub. attacked with a nucleophile (basic conditions)
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