SECTION 16 ² REACTIONS AND SYNTHESIS OF ALCOHOLS
16-1 -- Nomenclature of Alcohols
x Principle Group/Chain Contains -OH
x Alkane Æ Alkanol, Alkanediol, etc«
x Common Names of Alcohols
16-2 -- Alcohols and Hydrogen Bonding
x Bond Dissociation Energy (BDE) of a Hydrogen Bond ~ 5kcal/mol in Energy
16-2 -- Acidities of Alcohols
x The Alkoxide Anion, ROx Factors that Stabilize the Alkoxide Ion
x pKa
16-3 -- Three Factors that Stabilize the Alkoxide Ion, ROx Inductive Effects and Electronegative Substituents
x Resonance Effects
x Branching ² Steric Hindrance Considerations
16-5 -- Formation of Alkoxide Ions
x Deprotonation of the Alcohol
x Acid-Base Reactions
x Strong Bases Required for Deprotonation
16-6 -- Converting Alkenes Æ Alcohols
x 4 Ways
x Various Reagents that Can Be Used (4 Reaction Types)
x Markovnikov vs. non-Markovnikov Regiochemistry
x Diol Formation
16-6 -- Converting Alkyl Halides Æ Alcohols
x Occurs via SN2 or SN1 Chemistry
16-7 -- Converting Alcohols Æ Alkenes
x Possible Carbocation Rearrangements
x Use of POCl3 to Avoid Rearrangement
16-7 -- Converting Alcohols Æ Alkyl Halides
x 4 Ways
x Use of HX, -or- SOCl2, -or- PBr3, -or- Ts-Cl
16-8 -- Reactions of Grignard Reagents with Carbonyl Compounds (C=O)
x R·-MgX + Ketone Æ 3° Alcohol
x R·-MgX + Aldehyde Æ 2° Alcohol
x R·-MgX + Formaldehyde Æ 1° Alcohol
x Alkyllithium Reagents (R-Li) Can Also Be Used
x Esters Add 2 Equivalents of R·-MgX
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16-9 -- Grignard Reaction and Carboxylic Acids?
x No Reaction ² The Acid ´Killsµ the Grignard Reagent
16-10 -- Oxidation and Reduction
x ´OIL RIGµ
x Oxidation Levels and Oxidation Numbers
x Assignment Rules for Oxidation Numbers of Carbon
16-12 -- Hydride (:H-) Reduction Reactions
x Use of Lithium Aluminum Hydride (LiAlH4) or ´LAHµ
x Use of Sodium Borohydride (NaBH4)
x Solvents Used with LiAlH4 = Diethyl Ether (Et2O) or Tetrahydrofuran (THF)
16-13 -- Types of Hydride Reactions ² 2 Types
x Reduction of Ketones and Aldehydes to Form Alcohols
x Reduction of Esters and Carboxylic Acids to Form Alcohols
x Why Can·t NaBH4 Reduce Carboxylic Acids??
16-14 -- Oxidation of Alcohols with Chromium VI Reagents (Cr+6)
x Jones Reagent
x H2Cr2O7 as the Oxidizing Agent
x Use of the Milder Oxidizing Agent Pyridinium Chlorochromate (PCC)
16-16 -- Use of Protecting Groups
x Protecting the Alcohol Functional Group (-OH)
x Use of TBS-Cl
x TBS-Cl vs. TMS-Cl
x Protection / Deprotection Steps
16-18 -- Thiols = ´Mercaptansµ
16-18 -- Nomenclature of Thiols
16-18 -- Preparation of Thiols ² 2 Ways
x Use of Hydrosulfide Anion, HS- in an SN2 Reaction
x Use of Thiourea, (NH2)2C=S
16-19 -- Oxidation of Thiols to Produce Disulfides (R-S-S-R·)
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SECTION 16 – REACTIONS AND SYNTHESIS OF
ALCOHOLS
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