Ch_322a_8.06

Ch_322a_8.06 - Addition of Sulfuric Acid to Alkenes Alkenes dissolve in cold concentrated H2SO4 because of an addition reaction that produces alkyl

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Addition of Sulfuric Acid to Alkenes Alkenes dissolve in cold concentrated H 2 SO 4 because of an addition reaction that produces alkyl hydrogen sulfates : CH 3 CH=CH 2 + H-O-S-O-H O = O CH 3 CHCH 3 + + O-S-O-H O - electrophilic addition nucleophilic addition CH 3 CHCH 3 + + O-S-O-H O - CH 3 CHCH 3 O-SO 3 H isopropyl hydrogen sulfate This reaction is regioselective and follows Markovnikov's rule: CH 3 -C=CH 2 CH 3 conc. H 2 SO 4 cold CH 3 CCH 3 CH 3 O-SO 3 H tert-butyl hydrogen sulfate
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Alcohols by Hydrolysis of Alkyl Hydrogen Sufates Alcohols (ROH) are formed by heating alkyl hydrogen sulfates in water. The sulfate ester bond is hydrolyzed: CH 3 CH OSO 3 H CH 3 isopropyl hydrogen sulfate H 2 O heat CH 3 CH OH CH 3 + HOSOH O = O isopropyl alcohol via RO-S-OH O alkyl hydrogen sulfate + O-H H : : H + The nucleophilic water attacks the sulfate ester function releasing the alcohol. Note:
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_8.06 - Addition of Sulfuric Acid to Alkenes Alkenes dissolve in cold concentrated H2SO4 because of an addition reaction that produces alkyl

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