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H 1. LDA 2. CH31 H J = J -H CH₂ Monocarbonyl compounds can be alkylated at the a position via the use of lithium diisopropylamide, a strong, sterically hindered base. Because only one carbonyl group is available to participate in resonance stabilization of the enolate, the a-hydrogens are less acidic than those of ẞ-dicarbonyl compounds and so a stronger base is necessary to completely convert the compound to the enolate. The reaction occurs in a polar aprotic solvent such as THF. Compounds such as esters, ketones, and nitriles are commonly alkylated via this procedure. Aldehydes, however, rarely give high yields in this procedure because they tend to undergo carbonyl condensation instead. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: & H :0: ga H

H 1. LDA 2. CH31 H J = J -H CH₂ Monocarbonyl compounds can be alkylated at the a position via the use of lithium diisopropylamide, a strong, sterically hindered base. Because only one carbonyl group is available to participate in resonance stabilization of the enolate, the a-hydrogens are less acidic than those of ẞ-dicarbonyl compounds and so a stronger base is necessary to completely convert the compound to the enolate. The reaction occurs in a polar aprotic solvent such as THF. Compounds such as esters, ketones, and nitriles are commonly alkylated via this procedure. Aldehydes, however, rarely give high yields in this procedure because they tend to undergo carbonyl condensation instead. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: & H :0: ga H

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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H 1. LDA 2. CH31 H J = J -H CH₂ Monocarbonyl compounds can be alkylated at the a position via the use of lithium diisopropylamide, a strong, sterically hindered base. Because only one carbonyl group is available to participate in resonance stabilization of the enolate, the a-hydrogens are less acidic than those of ẞ-dicarbonyl compounds and so a stronger base is necessary to completely convert the compound to the enolate. The reaction occurs in a polar aprotic solvent such as THF. Compounds such as esters, ketones, and nitriles are commonly alkylated via this procedure. Aldehydes, however, rarely give high yields in this procedure because they tend to undergo carbonyl condensation instead. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: & H :0: ga H
Transcribed Image Text:H 1. LDA 2. CH31 H J = J -H CH₂ Monocarbonyl compounds can be alkylated at the a position via the use of lithium diisopropylamide, a strong, sterically hindered base. Because only one carbonyl group is available to participate in resonance stabilization of the enolate, the a-hydrogens are less acidic than those of ẞ-dicarbonyl compounds and so a stronger base is necessary to completely convert the compound to the enolate. The reaction occurs in a polar aprotic solvent such as THF. Compounds such as esters, ketones, and nitriles are commonly alkylated via this procedure. Aldehydes, however, rarely give high yields in this procedure because they tend to undergo carbonyl condensation instead. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: & H :0: ga H
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