Chem 263 - Lecture Outline & Assignment #3

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 11 – Alcohols and Ethers - review, especially nomenclature and properties
• Chapter 12 – Alcohols from Carbonyl Compounds - review
• Chapter 16 – Aldehydes and Ketones - Carbonyl Reactions
• Chapter 17 – Aldehydes and Ketones – Reactions at alpha-Carbon, Aldol
• Chapter 22 – Carbohydrates – read for overview structure and properties

Problems:

Do Not turn in, answers available in "Study Guide and Solutions Manual for Organic Chemistry" by Solomons and Fryhle..

Chapter 11:
11.6; 11.13; 11.25; 11.26

Chapter 12:
12.6; 12.7; 12.11 a to f; 12.12

Chapter 16:
16.2; 16.5; 16.7; 16.9; 16.10; 16.17; 16.23; 16.26; 16.37

Chapter 17:
17.1; 17.2; 17.7; 17.14; 17.19; 17.35 a and b

Chapter 22:
22.1; 22.2; 22.4; 22.11; 22.20; 22.28

Lecture Outline 3: Review of Stereochemistry, Alcohols and Ethers; Aldehydes & Ketones - Properties of the Carbonyl Group

1. Review of Structure, Nomenclature and Physical Properties of Alcohols and Ethers
   
   
   1. Aliphatic Alcohols
      
      
   2. Aromatic Alcohols (Phenols)
      
      
   3. Ethers
      
      
   4. Alcohols and Phenols - general properties
      
      1. MP, BP, solubility, density - hydrogen bonding
      2. Acidity of Aliphatic Alcohols (ROH)
         
         
   5. Acidity of Phenols (ArOH) - resonance
      
      
   6. Physical Properties of Ethers
      
      
      
2. Review of Stereochemistry - "Fixed three dimensional arrangements"
   
   
   1. The Concept of Chirality
      
      1. Identification of chiral objects and molecules - definitions
      2. Types of stereoisomers - enantiomers and diastereomers
      3. Racemic mixtures - 50-50 mixtures of enantiomers
         
         
   2. The R and S  Nomenclature System
      
      1. Rules for assignment of R and S configurations
         
         
   3. Molecules with more than one chiral center
      
      1. Enantiomers and Diastereomers
      2. Meso compounds - chiral centers with plane of symmetry within molecule
      3. Recognition of chiral centers in complex molecules
         
         
         
         
3. Structure, Nomenclature, Properties of Aldehydes and Ketones
   
   
   1. Nature of the Carbonyl Group - Physical Properties
      1. Polarity and Reactivity
      2. Hybridization and shape (sp², planar)
      3. Physical Properties - BP, MP, solubility, smell
         
         
   2. Nomenclature of Aldehydes - RCHO
      1. IUPAC - alkane name, replace "e" with "al"
         
         
   3. Nomenclature of Ketones - RCOR
      1. IUPAC - alkane name - replace "e" with "one"
         
         
         
4. Preparation of Aldehydes and Ketones
   
   
   1. Aldehydes
      1. Oxidation of Primary Alcohol: RCH₂OH  -> RCHO
      2. Reduction of Acyl Halides: RCOX  -> RCHO
         
         
   2. Ketones
      1. Friedel-Crafts Acylations
      2. Oxidation of 2° Alcohols: R₂CHOH to  R₂CO
      3. With Organometals: RMgX, R₂Cd, R₂CuLi
         
         
         
5. Reactions of Aldehydes and Ketones
   
   
   1. Nucleophilic Additions at the Carbonyl Carbon Atom
      1. General considerations - strong vs. weak nucleophiles
      2. Cyanohydrin formation
      3. Grignard reagent addition
      4. Reduction (hydride addition)
      5. Hemiacetal and Acetal formation
         
         
   2. Nucleophilic Addition - Elimination at the Carbonyl Carbon
      1. Wittig Reaction
      2. Addition of Derivatives of Ammonia: formation of oximes, hydrazones, imines
      3. Cannizzaro Reaction of Aldehydes with no alpha hydrogen
         
         
   3. Reactions at the alpha-carbon
      1. Enolate formations - Keto - enol tautomerism
      2. Halogenation and Haloform Reaction
      3. Alkylation
      4. Aldol Addition
         
         
   4. Reactions of alpha,beta-unsaturated aldehydes and ketones
      1. Conjugate Addition vs Simple Addition
         
         
         
6. Carbohydrates
   
   
   1. Monosaccharides
      1. Classification - aldose, ketose, triose, tetrose, etc.
      2. Stereoisomerism
      3. Anomers and Ring Formation (Hemiacetals, Acetals)
      4. Properties and Sweet Taste
         
         
   2. Disaccharides and Polysaccharides
      1. Sucrose
      2. Cellulose, Starch, Glycogen