Section 16 - Reactions and Synthesis of Alcohols

Reactions and Synthesis of Alcohols -- Section 16 of Organic Chemistry Notes is 19 pages in length (page 16-1 through page 16-19) and covers ALL you'll need to know on the following lecture/book topics:

SECTION 16 – Reactions and Synthesis of Alcohols

16-1 -- Nomenclature of Alcohols
  · Principle Group/Chain Contains -OH
  · Alkane --> Alkanol, Alkanediol, etc…
  · Common Names of Alcohols
16-2 -- Alcohols and Hydrogen Bonding
  · Bond Dissociation Energy (BDE) of a Hydrogen Bond ~ 5kcal/mol in Energy
16-2 -- Acidities of Alcohols
  · The Alkoxide Anion, RO-
  · Factors that Stabilize the Alkoxide Ion
  · pKa
16-3 -- Three Factors that Stabilize the Alkoxide Ion, RO-
  · Inductive Effects and Electronegative Substituents
  · Resonance Effects
  · Branching – Steric Hindrance Considerations
16-5 -- Formation of Alkoxide Ions
  · Deprotonation of the Alcohol
  · Acid-Base Reactions
  · Strong Bases Required for Deprotonation
16-6 -- Converting Alkenes --> Alcohols
  · 4 Ways
  · Various Reagents that Can Be Used (4 Reaction Types)
  · Markovnikov vs. non-Markovnikov Regiochemistry
  · Diol Formation
16-6 -- Converting Alkyl Halides --> Alcohols
  · Occurs via SN2 or SN1 Chemistry
16-7 -- Converting Alcohols --> Alkenes
  · Possible Carbocation Rearrangements
  · Use of POCl3 to Avoid Rearrangement
16-7 -- Converting Alcohols --> Alkyl Halides
  · 4 Ways
  · Use of HX, -or- SOCl2, -or- PBr3, -or- Ts-Cl
16-8 -- Reactions of Grignard Reagents with Carbonyl Compounds (C=O)
  · R’-MgX + Ketone --> 3° Alcohol
  · R’-MgX + Aldehyde --> 2° Alcohol
  · R’-MgX + Formaldehyde --> 1° Alcohol
  · Alkyllithium Reagents (R-Li) Can Also Be Used
  · Esters Add 2 Equivalents of R’-MgX
16-9 -- Grignard Reaction and Carboxylic Acids?
  · No Reaction – The Acid “Kills” the Grignard Reagent
16-10 -- Oxidation and Reduction
  · “OIL RIG”
  · Oxidation Levels and Oxidation Numbers
  · Assignment Rules for Oxidation Numbers of Carbon
16-12 -- Hydride (:H-) Reduction Reactions
  · Use of Lithium Aluminum Hydride (LiAlH4) or “LAH”
  · Use of Sodium Borohydride (NaBH4)
  · Solvents Used with LiAlH4 = Diethyl Ether (Et2O) or Tetrahydrofuran (THF)
16-13 -- Types of Hydride Reactions – 2 Types
  · Reduction of Ketones and Aldehydes to Form Alcohols
  · Reduction of Esters and Carboxylic Acids to Form Alcohols
  · Why Can’t NaBH4 Reduce Carboxylic Acids??
16-14 -- Oxidation of Alcohols with Chromium VI Reagents (Cr+6)
  · Jones Reagent
  · H2Cr2O7 as the Oxidizing Agent
  · Use of the Milder Oxidizing Agent Pyridinium Chlorochromate (PCC)
16-16 -- Use of Protecting Groups
  · Protecting the Alcohol Functional Group (-OH)
  · Use of TBS-Cl
  · TBS-Cl vs. TMS-Cl
  · Protection / Deprotection Steps
16-18 -- Thiols = “Mercaptans”
16-18 -- Nomenclature of Thiols
16-18 -- Preparation of Thiols – 2 Ways

  · Use of Hydrosulfide Anion, HS- in an SN2 Reaction
  · Use of Thiourea, (NH2)2C=S
16-19 -- Oxidation of Thiols to Produce Disulfides (R-S-S-R’)

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