Section 16 - Reactions and Synthesis of Alcohols
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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:
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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