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Chapter 11 - Wade(1)

Chapter 11 - Wade(1) - Introduction to General and Organic...

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Chapter 11 Reactions of Alcohols Dr. David P. Brown St. John’s University Introduction to General and Organic Chemistry III _____________________________
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Chapter 11 2 Typical Alcohol Reactions Dehydration to alkenes Oxidation to aldehydes or ketones Substitution to form alkyl halides Reduction to alkanes Esterification Tosylation Williamson synthesis of ethers =>
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Chapter 11 3 Oxidation Easy for inorganic salts
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Chapter 11 4 Oxidation of 1° Alcohols 1° alcohol initially oxidizes to aldehyde Difficult to stop at aldehyde Use pyridinium chlorochromate (PCC) to limit the oxidation . PCC can also be used to oxidize 2° alcohols to ketones. CH 3 CH 2 CH 2 CH 2 OH N H CrO 3 Cl CH 3 CH 2 CH 2 CH O
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Chapter 11 5 Oxidation of 2° Alcohols A 2° alcohol oxidizes to a ketone • Reagent is Na 2 Cr 2 O 7 /H 2 SO 4 Active reagent probably H 2 CrO 4 Color change : orange to greenish-blue CH 3 CHCH 2 CH 3 OH Na 2 Cr 2 O 7 / H 2 SO 4 CH 3 CCH 2 CH 3 O
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Chapter 11 - Wade(1) - Introduction to General and Organic...

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