厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十一章 醇和醚（11.4-11.13）Synthesis of Alcohols From Alkenes

ORGANIC CHEMISTRY Chapter ll 11. 4 Synthesis of Alcohols from Alkenes Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.4 Synthesis of Alcohols From Alkenes

ORGANIC CHEMISTRY Chapter ll C=C、——C-C-OH g Acid-Catalyzed hydration of alkenes o Oxymercuration-Demeruration o Hydroboration-Oxidation Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 C C C C H OH Acid-Catalyzed hydration of Alkenes Oxymercuration-Demeruration Hydroboration-Oxidation

ORGANIC CHEMISTRY Chapter ll 11.5 Alcohols From Alkenes Through Oxymercuration-Demercuration (1)Hg(OAc), H2O CH3 )CH3 (2) Nabha OH929 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.5 Alcohols From Alkenes Through Oxymercuration-Demercuration CH3 (1) Hg(OAc)2, H2O (2) NaBH4 CH3 OH 92%

ORGANIC CHEMISTRY Chapter ll 11.6 Hydroboration: Synthesis of Organoboranes HI:B-H H,δ H H H B H B---H CH H CH H CH3 H≈ B H H HC Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.6 Hydroboration: Synthesis of Organoboranes H H H H CH3 B H HH H CH3 B δ− δ+ δ+ H B H H CH3 H B H H H H H3C

ORGANIC CHEMISTRY Chapter ll 11.7 Alcohols from Alkenes Though Hydroboration-Oxidation 3RCH=CH2 B2H6 (RCH2 CH2)3B Hydroboration (RCH CH2)3B BRCHoCHOOH OH Oxidation B(OH)3 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.7 Alcohols from Alkenes Though Hydroboration-Oxidation 3RCH CH2 + B2H6 3RCH2CH2OH + B(OH)3 (RCH2CH2)3B (RCH2CH2)3B H2O2 OH Oxidation Hydroboration

ORGANIC CHEMISTRY Chapter ll 11. 8 Reactions of alcohols Nucleophile Nucleophilic substitution C-0 H H Oxidation Acidity Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.8 Reactions of Alcohols C H O H δ+ δ δ+ Nucleophile Nucleophilic substitution Oxidation Acidity

ORGANIC CHEMISTRY Chapter ll Unstable Alcohols CH -CH-OH Ch c-H OH CHrch CH3 C-H +H,O OH CH3-C-CH3 CH3C-CH3 H2O OH OH CH3CH CH3C-H +hc CI Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 Unstable Alcohols CH2 CH OH CH3C O H CH3CH OH OH CH3C O H C OH OH CH3 CH3 C O CH3 CH3 CH3CH OH Cl CH3C O H + H2O + H2O + HCl

ORGANIC CHEMISTRY Chapter ll 11 9 Alcohols as acids Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.9 Alcohols as Acids

ORGANIC CHEMISTRY Chapter ll Compounds (CH3)3 COH 18.00 CHrCH,OH 16.00 HOH 15.74 ChOH 15.54 CF3 CHOH 12.43 (CF3) COH 54 HCl 7.00 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 18.00 16.00 15.74 15.54 12.43 5.4 7.00 Compounds pKa (CH3)3COH CH3CH2OH HOH CH3OH CF3CH2OH (CF3)3COH HCl

ORGANIC CHEMISTRY Chapter ll ROH Na RONa +h Reactivity Ch3oH> CH3,OH> CH3 CH,CH,OH> CH3)2CHOH >(CH3)3COH CH3 CH,ONa H,O ch choo naoh Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 + Na RONa + H2 Reactivity CH3OH > CH3CH2OH > CH3CH2CH2OH > (CH3)2CHOH > (CH3)3COH ROH CH3CH2ONa + H2O CH3CH2OH + NaOH