CHEM 3410 1st Edition Lecture 12Outline of CurrentI. Table of Rules II. Alcohols IntroductionA. Primary, Secondary, Tertiary B. NamingC. Propertiesi. Hydrogen Bondingii. Rule of 8iii. Acidity/ Basicity Outline of Last LectureIII. Table of RulesIV. Directing Effects and ReactivityV. Synthesis VI. Nucleophilic Aromatic Substitution A. Resonance Mechanisms Current LectureI. Table of RulesSubstituent More or less reactive than BenzeneReactivity Directing EffectInductive Effect Resonance EffectH N/A N/A N/A N/A N/ACH3 (or anyR group)Slightly more reactive Activating O,P Donating N/aOH, NH2A lot more reactiveActivating O,P Donating DonorF, Cl, Br, I Slightly less reactiveDeactivating O,P Withdrawing DonorNO2, Cyano A lot less reactiveStrongly DeactivatingM (Strongly) Withdrawing(Strongly) WithdrawingThese notes represent a detailed interpretation of the professor’s lecture. These notesare best used as a supplement to your own notes, not as a substitute.Carbonyls A lot less reactiveStronglyDeactivating M (Strongly) Withdrawing(Strongly) WithdrawingII.Introduction to AlcoholsA. Primary, Secondary, Tertiary Alcohols are polar and organic. They mix well with organic and inorganic materials.B. NamingC. PropertiesHydrogen bondingCompared to other molecules, alcohols will have higher viscosity, melting points, boiling points….alcohols will have higher physical properties than alkenes and other organic molecules because of hydrogen bonding. Charge distribution interaction:This is why alcohols are fully miscible with water.Rule of 88 or more carbons on an alcohol will not mix with water because the charge distribution interaction is disrupted through the addition of 8 or more carbons. Also, remember that the more atoms, the higher the physical properties.Acidity/ BasicityGeneral Rules:Withdrawing groups make alcohol more acidic. Higher substitution causes the molecule to be less acidic.Primary > Secondary > TertiaryPhenols are more acidic than linear alcoholsThe closer the EWD effects to the oxygen of the alcohol, the more acidic it will be. Inductive effects diminish through
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