Carboxylic Acid Derivatives

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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Nucleophilic Acyl Substitution Reactions

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