The two steps, an intramolecular Michael reaction and the following intramolecular aldol reaction, involved in the reaction along with their mechanisms are to be given. Concept introduction: The steps involved are i) Deprotonation of an acidic hydrogen ii) Internal Michael addition iii) Proton exchange iv) Internal aldol condensation v) Protonation. To give: The two steps, an intramolecular Michael reaction and the following intramolecular aldol reaction, involved in the reaction along with their mechanisms.

Question

Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

Answer 1

Question

Chapter 23.SE, Problem 41MP

Interpretation Introduction

Interpretation:

The two steps, an intramolecular Michael reaction and the following intramolecular aldol reaction, involved in the reaction along with their mechanisms are to be given.

Concept introduction:

The steps involved are i) Deprotonation of an acidic hydrogen ii) Internal Michael addition iii) Proton exchange iv) Internal aldol condensation v) Protonation.

To give:

The two steps, an intramolecular Michael reaction and the following intramolecular aldol reaction, involved in the reaction along with their mechanisms.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?

1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH