Chapter 17 September 28 - New Method: 6 Reactions of...

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1 Protection of Alcohols: Sometimes the reaction conditions necessary for the conversion of specific functional groups are incompatible with other groups present in the molecule Example: 3 General Steps of Protection Group Chemistry: 1.) 2.) 3.) Introduction of a protecting group to block interference (reactivity) Primary reaction execution (protecting group must be stable in these reaction conditions) Removal of the protecting group
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2 Common Alcohol Protecting Group: TMS Mechanism: Example Reaction: Use Chlorotrimethyl silane (w/ Et 3 N) to form a trimethyl silyl ether with the alcohol group
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3 TMS Reactivity: TMS ethers are relatively unreactive due to the fact that they have no acidic hydrogens: Mechanism of Deprotection: No Oxidation No Reduction No grignard reactions or deprotonations
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4 Sample Synthesis Problem:
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5 Preparation of Phenol: Review:
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Unformatted text preview: New Method: 6 Reactions of Phenols Oxidation Redox Reactions Numerous electrophilic aromatic substitutions (Review) Oxidations reactions (quinone formation) 7 Spectroscopy of Alcohols and Phenols Infrared Spectroscopy: 8 Proton NMR Spectroscopy of Alcohols and Phenols: Reason: H's on the carbon atom adjacent to a hydroxyl group are deshielded (EWG effect) and end up downfield These same H's do not show any spin spin splitting with regards to the hydroxyl group hydrogen Alcohol group hydrogen typically absorbs at 2.5 5 9 Chapter 18: Ethers, Epoxides, Thiols, and Sulfides Ethers: Quick Structural Comparisons: Alcohols: Ethers: Thiols: Sulfides: Relatively unreactive/stable. Good for solvents. Can form explosive peroxides (ROOR') Attachments Nitration Rxn Quiz.doc...
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This note was uploaded on 12/20/2011 for the course CHEM 234-54 taught by Professor Morrison during the Fall '09 term at University of Georgia Athens.

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Chapter 17 September 28 - New Method: 6 Reactions of...

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