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
Monday, July 21, 14
Reduction of the Carbonyl Group
Uses of NaBH4 and LiAlH4
Monday, July 21, 14
Reduction of the Carbonyl Group
Uses of NaBH4 and LiAlH4
Monday, July 21, 14
Exercise
Show how you would synthesize the following alcohols by reducing appropriate carbonyl compounds
Monday, July 21, 14
1. Draw the organic products you would expect to isolate from the following reactions (after hydrolysis)
AssignmentDeadline : August 4th 2014
Monday, July 21, 14
AssignmentDeadline : August 4th 2014
Monday, July 21, 14
AssignmentDeadline : August 4th 20142. Show how you would accomplish the
following transformations. You may use any additional reagents you need.
Monday, July 21, 14
AssignmentDeadline : August 4th 2014
Monday, July 21, 14
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