This reaction shows that an aldol-type reaction can be performed with a deprotonated imine as the nucleophile. On hydrolysis, the product is the normal B-hydroxycarbonyl compound. Notice that LDA is used H3C N. 1. LDA Но ? as the base instead of HO¯. H3C H. H. (a) Explain why HO¯ cannot be used as a base for this 2. reaction. (b) Provide a detailed mechanism for this reaction, including the structure of the intermediate species not shown.

This reaction shows that an aldol-type reaction can be performed with a deprotonated imine as the nucleophile. On hydrolysis, the product is the normal B-hydroxycarbonyl compound. Notice that LDA is used H3C N. 1. LDA Но ? as the base instead of HO¯. H3C H. H. (a) Explain why HO¯ cannot be used as a base for this 2. reaction. (b) Provide a detailed mechanism for this reaction, including the structure of the intermediate species not shown.

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

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Draw the major product of the aldol addition reaction between two equivalents of this ketone with the conditions provided. Ignore inorganic byproducts. 1. H3O+ 2. Neutralizing work-up &
B. Dieckmann Condensations Just as there can be intramolecular Aldol condensations, so can there be intramolecular Claisen condensations. These are called Dieckmann condensations. 1) Identify all the a hydrogens in the diester shown. Draw the enolate anion(s) that form when the hydrogen(s) is/are removed. H3CH₂CO OCH₂CH3 2) Draw a mechanism and provide the product(s) formed when the anion(s) attack(s) the other carbonyl carbon in the molecule. All electron movement must be shown with arrows.
2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible). NaOH/H₂O A CH3 a. b. C. H₂C Draw the structure for the enolate ion (show both of the relevant resonance structures). Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)
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4. In the following compound: (a). Circle the good leaving group. (b). Explain why it is a good leaving group. HO,