Lecture38 - Ammonia and amines react with the carbonyl...

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11/29/09 1 Addition of Alcohols Formation of Acetals and Ketals Addition of one molecule of alcohol to an aldehyde forms a hemiacetal: a hemiacetal Addition of Alcohols Formation of Acetals and Ketals Addition of one molecule of alcohol to a ketone forms a hemiketal: a hemiketal
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11/29/09 2 Addition of Alcohols Formation of Acetals and Ketals Hemiacetals and hemiketals react further with alcohols to form acetals and ketals. These reactions are acid catalyzed . a hemiacetal Addition of Alcohols Formation of Acetals and Ketals Hemiacetals and hemiketals react further with alcohols to form acetals and ketals. These reactions are acid catalyzed . 1,1-dimethoxyethane (a dimethyl acetal) a hemiacetal
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11/29/09 3 Addition of Alcohols Formation of Acetals and Ketals Hemiacetals and hemiketals react further with alcohols to form acetals and ketals. These reactions are acid catalyzed . a hemiketal 2,2-diethoxypropane (a diethyl ketal) Addition of Ammonia and Its Derivatives
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Unformatted text preview: Ammonia and amines react with the carbonyl group of aldehydes and ketones in the presence of an acid catalyst to give products that contain a carbonnitrogen double bond: 11/29/09 4 Addition of Ammonia and Its Derivatives Ammonia and amines react with the carbonyl group of aldehydes and ketones in the presence of an acid catalyst to give products that contain a carbonnitrogen double bond: an imine (a Schiff base) Mechanism for Imine Formation Step One Protonation of carbonyl: 11/29/09 5 Mechanism for Imine Formation Step One Protonation of carbonyl: Mechanism for Imine Formation Step Two Nucleophilic addition of amine: 11/29/09 6 Mechanism for Imine Formation Step Two Nucleophilic addition of amine: Mechanism for Imine Formation Step Three Proton reorganization: 11/29/09 7 Mechanism for Imine Formation Step Four Elimination: Mechanism for Imine Formation Step Four Elimination:...
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Lecture38 - Ammonia and amines react with the carbonyl...

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