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MCAT O Chem

Ch. 7 Alcohols and Ethers

QuestionAnswer
pKa pKa=-logKa. strong acids have high Ka's and small pka's. Phenol has small pka so most acidic of alcohols listed
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
how can phenols be synthesized arylsulfonic acids with hot NaOH. Or hydrolysis of diazonium salts.
Reducing agents Have lots of H's (NaBH4 and LiAlH4), oxidizing agents have lots of O's (KMnO4 and CrO3)
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
Jones's oxidation chromium trioxide, CrO3 dissolved with dilute sulfuric acid in acetone. oxidized primary alcohols to carboxylic acids and secondary alcohols to ketones
treatments of phenols with oxidizing reagents produces what quinones
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
williamson either synthesis produces ethers from the reaction of metal alkoxides with primary alkyl halides or tosylates
epoxide or oxrine formation oxidation of an alkene with peroxy acid (RCOOOH)
peroxides and ether ethers react with oxygen in air to form highly explosive compounds called peroxides
strong bases as leaving group are poor leaving groups
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)
Created by: adam87
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