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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Reactions and Synthesis of Alcohols

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