Section 20 - Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions
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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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