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Reactions of Alcohols • • • • • • • • Reaction Summary: 4. Hydration: Alkene + water --> alcohol 7. Dehydration: Alcohol + heat --> alkene + H2 8. Oxidation: Pri. Alcohol + (O) --> aldehyde 9. Oxidation: Sec. Alcohol + (O) --> ketone 9B. Oxidation: Tert. Alcohol + (O) --> no reaction 10.Oxidation: Aldehyde + (O) --> Acid 11. Ether Synthesis: Alcohol + alcohol --> ether + HOH 4. Hydration Reaction • Alkene + HOH --> alcohol • HOH molecule adds to carbons with double bond. H3C H3C CH CH3 H C CH2 + HOH H3C H C HO C H H HO H Mark's Rule H H3C C H C OH H H 7. Dehydration of Alcohol to Alkene • Subtraction: Remove -OH from alcohol carbon • Remove -H from a neighbor carbon H H3C CH OH H3C H H H H H C C H3C O CH2 OH H 3C CH Reactions of Alcohols 8. Oxidation of Primary Alcohol to Aldehyde • Subtraction: Remove -H from alcohol group • Remove -H from alcohol carbon H H3 C H2 C C H2 OH H2 H O C H3C C O H (O) + H H H3C H2 C O C H Reactions of Alcohols 9. Oxidation of Secondary Alcohol to Ketone • Subtraction: Remove -H from alcohol group • Remove -H from alcohol carbon H H3C H H OH CH O O CH3 H3C C H + (O) CH3 O H3C C CH3 Reactions of Alcohols Reactions of Alcohols Reactions of Alcohols Reactions of Alcohols Reactions of Alcohols CH3 CH H3C CH3 CH + (O) OH CH3 H2C H3C CH H2C H2 C H3C + (O) OH H2 C + SH H 3C + (O) SH 10. Oxidation of Aldehyde to Acid • Add oxygen from oxidizing agent • Insert O between H of carbon double oxygen H3C H2 C O C H H3C H2 C C O + (O) H O H 3C C H2 C OH 11. Ether synthesis from 2 alcohols • Subtraction: Remove -H from one alcohol group • Remove -OH from other alcohol carbon • Join two parts O H H3C H2 C O H + HO H2 C CH3 H3 C H2 C O H H2 C CH3 Reactions of Alcohols CH3 CH3 HO CH CH3 + HO CH CH3