Structure and Synthesis Alcohols
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Structure and Synthesis Alcohols By: Isman Kurniawan Monday, July 21, 14
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Structure and Synthesis Alcohols
Transcript of Structure and Synthesis Alcohols
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Structure and Synthesis AlcoholsBy: Isman Kurniawan
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Introduction
Compounds containing hydroxyl (-OH) groups.
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Structure and Classification
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Structure and Classification
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Physical Properties of Alcohols
Boiling points
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Physical Properties of Alcohols
Solubility properties
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Acidity of Alcohols and Phenols
Hydroxyl proton of an alcohol is weakly acidic.
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Acidity of Alcohols and Phenols
Effects on acidity
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Acidity of Alcohols and Phenols
Effects on acidity
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Acidity of Alcohols and Phenols
Formation of sodium and potassium alkoxides
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Acidity of Alcohols and Phenols
Acidity of phenols
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Acidity of Alcohols and Phenols
Acidity of phenols
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Synthesis of Alcohols:Introduction and Review Nucleophilic substitution on an alkyl halide
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Synthesis of Alcohols:Introduction and Review Synthesis of alcohols from alkenes Acid-catalyzed hydration
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Synthesis of Alcohols:Introduction and Review Synthesis of alcohols from alkenes Hydroxylation
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Organometallic Reagents for Alcohol Synthesis
Grignard reagents
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Exercise
Predict the products of the following reactions
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Addition of Organometallic Reagents to Carbonyl Compounds
Mechanism
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Addition of Organometallic Reagents to Carbonyl Compounds
Mechanism
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Addition of Organometallic Reagents to Carbonyl Compounds
Addition to formaldehyde: formation of primary alcohols
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Exercise
Show how you would synthesize the following alcohols by adding an appropriate Grignard reagent to formaldehyde
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Addition of Organometallic Reagents to Carbonyl Compounds
Addition to aldehydes: formation of secondary alcohols
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Exercise
Show how you would synthesize the following alcohols by adding an appropriate Grignard reagent to aldehyde
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Addition of Organometallic Reagents to Carbonyl Compounds
Addition to ketones: formation of tertiary alcohols
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Exercise
Show how you would synthesize the following alcohols by adding an appropriate Grignard reagent to ketone
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Addition of Organometallic Reagents to Carbonyl Compounds
Addition to ethylene oxide
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Exercise
Show how you would synthesize the following alcohols by adding an appropriate Grignard reagent to ethylene oxide
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Reduction of the Carbonyl Group
The two most useful hydride reductor reagents: NaBH4 and LiAlH4
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Reduction of the Carbonyl Group
Mechanism
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Reduction of the Carbonyl Group
Uses of NaBH4 and LiAlH4
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Reduction of the Carbonyl Group
Uses of NaBH4 and LiAlH4
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Reduction of the Carbonyl Group
Uses of NaBH4 and LiAlH4
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Exercise
Show how you would synthesize the following alcohols by reducing appropriate carbonyl compounds
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1. Draw the organic products you would expect to isolate from the following reactions (after hydrolysis)
AssignmentDeadline : August 4th 2014
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AssignmentDeadline : August 4th 2014
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AssignmentDeadline : August 4th 20142. Show how you would accomplish the
following transformations. You may use any additional reagents you need.
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AssignmentDeadline : August 4th 2014
Monday, July 21, 14
