Chem 164/261 - Lecture Outline & Assignment #5

Readings
Problems
Outline
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Readings:

Organic Chemistry, L Wade, UA Custom Edition, 2013, Volume 1 (Chem 164/261)

• Functional Group List - Inside Front Cover (also Handout)
  • Chapter 7 – Review Substitution Reactions of Alkyl Halides to Give Alcohols and Ethers
  • Chapter 9 – Review Reactions of Alkenes to form Alcohols and Ethers
  • Chapter 11 – Structure and Synthesis of Alcohols
  • Course Handout on Carbohydrates: Nomenclature & Properties

Problems:

Do Not turn in, answers available in "Student Solutions Manual for Organic Chemistry" for LG Wade

(do all “solved problems” in chapters listed below)

• Chapter 11: 11-1 to 11.5; 11.7 to 11.16; 11.31 to 11.33; 11.39

 

Lecture Outline 5:
Alcohols, Ethers & Introduction to Carbohydrates

1. Structure and Nomenclature of Alcohols and Ethers
   
   
   1. Aliphatic Alcohols
      1. IUPAC system
      2. Common names – carbinol system, "alcohol" names
   
   
   2. Aromatic Alcohols (Phenols)
   
   
   3. Ethers
      1. Common names
      2. IUPAC system – “alkoxy"
   
   


2. Physical Properties
   
   
   1. Alcohols and Phenols – general properties
      1. MP, BP, solubility, density – hydrogen bonding
      2. Acidity of aliphatic alcohols (ROH) and ArOH
   
   
   2. Physical Properties of Ethers
   
   


3. Preparation of Alcohols and Phenols (Review – Parts A & B Previously Discussed in Class)
   
   
   1. From Alkenes – Aliphatic Alcohols (ROH)
      1. Hydration (H20, H+)
      2. Oxymercuration – Demercuration [Hg(OAc)2 then NaBH4]
      3. Hydroboration – Oxidation [B2H6 then H2O2, KOH ]
   2. From Alkyl Halides: Nucleophilic Substitution Reactions (SN1 and SN2)
   
   
   3. Grignard Reagents & Grignard Reactions – Addition to Carbonyl
   
   
   4. Hydride Addition to Carbonyls (Ketones & Aldehydes)


4. Reactions of Alcohols and Phenols
   
   
   1. Reactions Breaking O–H Bond
      1. Acid–base – alcohols as acids
      2. Ester formation
      3. Ether formation
      4. Oxidation
   
   
   2. Reactions Breaking C–O Bond
      1. Dehydration to alkenes
      2. Formation of alkyl halide
   
   


5. Ethers (Review – Previously Discussed in Class)
   
   
   1. Preparation
      1. Mercuration – Demercuration of alkenes in alcohols
      2. Epoxidation of alkenes
      3. From alcohols by removal of H2O
      4. From alkyl halides or sulfonates
   
   
   2. Reaction of Ethers
      1. Cleavage of ethers to alcohols
   
   


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