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Section 20 - Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions - Section 20 of Organic Chemistry Notes is 27 pages in length (page 20-1 through page 20-27) and covers ALL you'll need to know on the following lecture/book topics:


SECTION 20 – Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions

20-1 -- General Classes and Nomenclature of Carboxylic Acid Derivatives
  · Acid Halides (“Alkanoyl Halides”)
  · Acid Anhydrides
  · Esters: Straight-Chained Esters and Cyclic Esters (“Lactones”)
  · Amides (“Alkanamides”; 1°, 2°, and 3°)
  · Cyclic Amides (“Lactams”)
  · Imides – 2 Fused Amides
  · Nitriles, R-CΞN: (“Alkanenitriles”)
20-5 -- Priority Order of Principle Groups in Carboxylic Acid Derivatives
  · Main Chain vs. Substituents (“Branches”)
  · Some Common Substituents
20-5 -- Structures, Properties, & Spectrosopy of Carboxylic Acid Derivatives
  · Esters Prefer to be Planar (Z-conformation vs. E-conformation)
  · IR Spectroscopy of Esters
  · IR Spectroscopy of Acid Anhydrides (asymmetric stretch & symmetric stretch)
  · Amides Prefer to be Planar
  · IR and 1H NMR for Amides
20-8 -- Reactions of Carboxylic Acid Derivatives (BIG TOPIC) – thru p.20-26
  · The Mechanism of Acyl Substitution Reactions Under Basic Conditions
  · The Mechanism of Acyl Substitution Reactions Under Acidic Conditions
  · Tetrahedral Intermediates, Reaction Rates, and Relative Stabilities
  · Relative Reactivities of Carboxylic Acid Derivatives
20-9 -- Hydrolysis Reactions (Addition of H2O)
  · Acid Halides + H2O --> ?
  · Acid Anhydrides + H2O --> ?
  · Esters (and Lactones) + H2O --> ? (acid-catalyzed vs. base-catalyzed)
  · Amides (and Lactams) + H2O --> ? (acid-catalyzed vs. base-catalyzed)
  · Nitriles + H2O --> ?
20-12 -- Reactions with Nucleophiles Other than Water
  · Acid Chlorides --> Esters (via use of Pyridine)
  · Acid Chlorides --> Amides
  · Acid Chlorides --> Anhydrides (involves use of a Carboxylate Salt)
  · Mixed Anhydrides
  · Dehydration of 2 Carboxylic Acids Produces an Anhydride
  · Anhydrides --> Esters
  · Cyclic Anhydrides --> One Half-Ester + One Half-Acid
  · Transesterification: Converting One Ester to Another Ester
  · Transesterification can be Acid-Catalyzed or Base-Catalyzed
  · Esters --> Amides
  · Acids --> Acid Chlorides
  · Use of SOCl2 (Thionyl Chloride) and PCl3 or PBr3
  · Acids --> Anhydrides (via use of P2O5)
  · Acids --> Esters (via acid-catalyzed mechanism only)
20-19 -- Summary of Carbonyl Substitution Reactions
20-19 -- Reactions of –COOH Derivatives with Carbanionic Nucleophiles, “:R-“
  · R-MgX (Grignard Reagent), R-Li (Alkyllithium Reagent), and R2CuLi Reagent
  · Acid Chlorides + Carbanionic Nucleophiles --> ?
  · Esters + Carbanionic Nucleophiles --> ?
  · Carboxylic Acids + Carbanionic Nucleophiles --> ?
20-21 -- Reactions with Hydride Equivalents (“:H-“) as Nucleophiles
  · “Reductions”
  · LiAlH4 (Lithium Aluminum Hydride) and NaBH4 (Sodium Borohydride)
  · Acid Chlorides --> Alcohols or Aldehydes
  · Use of LiAlH(OtBu)3 – Bulkier Version of LiAlH4
  · Anhydrides --> 2 Alcohols
  · Esters --> Alcohols or Aldehydes
  · Use of DIBAH (Diisobutylaluminum hydride)
  · Acids --> Alcohols (via LiAlH4 or borane, BH3)
  · Amides --> Amines (using LiAlH4)
20-26 – The Chemistry of Nitriles, R-CΞN:
  · Preparation of Nitriles (via SN2, or P2O5, or SOCl2, or POCl3)
20-26 – Reactions of Nitriles
  · Reduction with LiAlH4 or DIBAH
  · Reduction with Grignard Reagent (R’-MgX)

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