Chem 161 - Lecture Outline & Assignment #5

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 (1 page back from Back Cover)
• Chapter 6 – Substitution Reactions (re-read alcohols from alkyl halides)
• Chapter 8 – Alkenes (re-read alcohols from alkenes)
• Chapter 11 – Alcohols and Ethers
• Chapter 21 – Phenols (read for overview sections 21.1 – 21.3 only)
• Chapter 22 – Carbohydrates (read sections 22.1 – 22.4 and sections 22.12 – 22.13)

Problems:

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

Chapter 11:
11.2 to11.4; 11.9; 11.13 to 11.16; 11.25 to 11.27; 11.34

Chapter 22:
22.1; 22.2; 22.6; 22.11; 22.20 (a, b, c, h, i, j, k, l, p, q, r)

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 – 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. By Nucleophilic Substitution Reactions (SN1 and SN2)
      1. Definitions: SN1 and SN2
      2. Mechanisms
   
   
   3. SN2 Reactions
      1. Stereochemistry – Walden Inversion (inversion of configuration)
      2. Substitution of primary and secondary alkyl halides
   
   
   4. SN1 Reactions
      1. Stereochemical aspects (loss of stereochemistry via carbocations)
      2. Substitution of tertiary alkyl halides and other tertiary carbons
      3. Synthesis of alcohols, ethers
   
   


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