Chem 263 - Lecture Outline & Assignment #4
Readings
Problems
Outline
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Readings:
TWG Solomons and CB Fryhle "Organic Chemistry" 8th Edition (2004):
- Functional Group List on pp 70-71 and (Periodic Table) one page back from Inside Back Cover
- Relative Strength of Acids and Bases on Inside Front Cover - same table page 105
- Chapter 18 – Carboxylic Acids and their Derivatives
- Chapter 19 – More Chemistry of Enolate Ions
- Sections 19.1 to 19.9 and 19.12
- Chapter 23 – Lipids
Problems:
Do Not turn in, answers available in "Study Guide and Solutions Manual for Organic Chemistry " by Marc Loudon and Joseph Stowell. This is available in the Bookstore or can be borrowed from Cameron Library's Reserve Reading Room.
Chapter 18:
18.1; 18.3; 18.5 to 18.11; 18.14; 18.19; 18.20; 18.24; 18.25; 18.29; 18.37; 18.39; 18.52
Chapter 19:
19.1; 19.2; 19.4; 19.6; 19.8; 19.15
Chapter 23:
23.9; 23.12
Lecture Outline 4: Carboxylic Acids and Their Derivatives
- Structure and Nomenclature - The Acyl Group
- Acids - RCOOH
- Acid Halides - RCOX
- Anhydrides - (RCO)2O
- Esters - RCOOR'
- Amides - RCONH2, RCONHR, RCONR2
- Carboxylic Acids
- Acidity and Physical Properties
- Preparation
- Oxidation of Alkenes
- Oxidation of Alcohols and Aldehydes
- Oxidation of Alkylbenzenes
- Oxidation of Methyl Ketones (Haloform reaction)
- Hydrolysis of Nitriles
- Carbonation of Grignard Reagents (RMgX + CO2)
- Reactions
- Salt formation
- Ester formation
- Reduction
- Acid Halides
- Physical Properties and Reactivity
- Preparation from Carboxylic Acids
- Reactions on Carbonyl Carbon - (Nucleophilic Substitution)
- Hydrolysis to Carboxylic Acids
- Anhydride Formation with Carboxylates
- Alcoholysis to Esters
- Ammonolysis to Amides
- Reduction to Alcohols or Aldehydes
- Friedel Crafts Acylations
- Reaction on alpha-carbon - Perkin Reaction
- Anhydrides
- Physical Properties
- Preparation
- From Acid Halides and Carboxylates
- Cyclic Dehydration of Diacids
- Reactions on Carbonyl Carbon
- Hydrolysis to Carboxylic Acids
- Alcoholysis to Ester and Acid
- Ammonolysis to Amide and Salt of Acid
- Reduction to Alcohols
- Friedel Crafts Acylations
- Reaction on alpha-carbon - Perkin Reaction
- Esters
- Physical Properties
- Preparation
- Alcoholysis of Acid Halides
- Alcoholysis of Anhydrides
- Esterification of Carboxylic Acids
- Primary and Secondary ROH
- Tertiary ROH
- Lactone formation
- Reactions at Carbonyl Carbon
- Acidic Hydrolysis - Acyl - Oxygen and Alkyl - Oxygen Cleavage
- Alkaline Hydrolysis - Acyl - Oxygen Cleavage
- Transesterification with Alcohols
- Ammonolysis to Amide and Alcohol
- Reduction to Alcohols
- Grignard Reaction
- Reactions at alpha-carbon
- Ester-Ester Condensation - Claisen and Dieckmann
- Ester-Ketone and Ester-Aldehyde Condensation
- Fats, Waxes, and Soaps
- Amides
- Physical Properties
- Preparation
- Ammonolysis of Acid Halides, Anhydrides, Esters
- Partial Hydrolysis of Nitriles
- Reactions at Carbonyl Carbon
- Hydrolysis
- Reduction to Amines
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