Structure and Synthesis

Alcohols
By: Isman Kurniawan

Monday, July 21, 14

Introduction
Compounds containing hydroxyl (-OH)
groups.

Monday, July 21, 14

Structure and
Classification

Monday, July 21, 14

Structure and
Classification

Monday, July 21, 14

Physical Properties of
Alcohols

Boiling points

Monday, July 21, 14

Physical Properties of
Alcohols

Solubility properties

Monday, July 21, 14

Acidity of Alcohols and

Phenols
Hydroxyl proton of an alcohol is weakly
acidic.

Monday, July 21, 14

Acidity of Alcohols and

Phenols
Effects on acidity

Monday, July 21, 14

Acidity of Alcohols and

Phenols
Effects on acidity

Monday, July 21, 14

Acidity of Alcohols and

Phenols
Formation of sodium and potassium
alkoxides

Monday, July 21, 14

Acidity of Alcohols and

Phenols
Acidity of phenols

Monday, July 21, 14

Acidity of Alcohols and

Phenols
Acidity of phenols

Monday, July 21, 14

Synthesis of Alcohols:
Introduction and Review
Nucleophilic substitution on an alkyl halide

Monday, July 21, 14

Synthesis of Alcohols:
Introduction and Review
Synthesis of alcohols from alkenes
Acid-catalyzed hydration

Monday, July 21, 14

Synthesis of Alcohols:
Introduction and Review
Synthesis of alcohols from alkenes
Hydroxylation

Monday, July 21, 14

Organometallic Reagents
for Alcohol Synthesis
Grignard reagents

Monday, July 21, 14

Exercise
Predict the products of the following
reactions

Monday, July 21, 14

Addition of Organometallic
Reagents to Carbonyl Compounds

Mechanism

Monday, July 21, 14

Addition of Organometallic
Reagents to Carbonyl Compounds

Mechanism

Monday, July 21, 14

Addition of Organometallic
Reagents to Carbonyl Compounds

Addition to formaldehyde: formation of

primary alcohols

Monday, July 21, 14

Exercise
Show how you would synthesize the

following alcohols by adding an appropriate

Grignard reagent to formaldehyde

Monday, July 21, 14

Addition of Organometallic
Reagents to Carbonyl Compounds

Addition to aldehydes: formation of

secondary alcohols

Monday, July 21, 14

Exercise
Show how you would synthesize the

following alcohols by adding an appropriate

Grignard reagent to aldehyde

Monday, July 21, 14

Addition of Organometallic
Reagents to Carbonyl Compounds

Addition to ketones: formation of tertiary

alcohols

Monday, July 21, 14

Exercise
Show how you would synthesize the

following alcohols by adding an appropriate

Grignard reagent to ketone

Monday, July 21, 14

Addition of Organometallic
Reagents to Carbonyl Compounds

Addition to ethylene oxide

Monday, July 21, 14

Exercise
Show how you would synthesize the

following alcohols by adding an appropriate

Grignard reagent to ethylene oxide

Monday, July 21, 14

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 NaBH

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and LiAlH4

Reduction of the
Carbonyl Group
Uses of NaBH

Monday, July 21, 14

and LiAlH4

Reduction of the
Carbonyl Group
Uses of NaBH

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and LiAlH4

Exercise
Show how you would synthesize the

following alcohols by reducing appropriate

carbonyl compounds

Monday, July 21, 14

Assignment
th
Deadline : August 4 2014
1. Draw the organic products you would
expect to isolate from the following
reactions (after hydrolysis)

Monday, July 21, 14

Assignment
th
Deadline : August 4 2014

Monday, July 21, 14

Assignment
th
Deadline : August 4 2014
2. Show how you would accomplish the
following transformations.You may use any
additional reagents you need.

Monday, July 21, 14

Assignment
th
Deadline : August 4 2014

Monday, July 21, 14