Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 24, Problem 24.17P
The following transformation involves a series of four consecutive Heck reactions and the formation of the four-ring steroid nucleus (Section 26.4) as a racemic mixture. Propose structural formulas for the palladium-containing intermediates involved in this reaction.
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Propose the synthesis for the following transformation.
Complete the statements by providing the reagents necessary to complete each step of the synthesis.
Ketone reacted with
CO₂H
and then
yielded a derivative, which was treated with
1) (i) C6H5MgBr (ii) H3O+
2) (i) DIBAL-H (ii). H3O+
3) Sia2BH,H202, NaOH
4) CH2N2 (diazamethane)
CO₂C2H5
5) PCC (an oxidant)
6) H2SO4, H2O, heat
7) HgSO4/ H2SO4
8) C₂H5OH, H3O*, heat
TABLE OF REAGENTS
to form an unsaturated carboxylic acid, treatment with
to yield unsaturated aldehyde as the final product.
CHO
MacBook Air
9) C6H5 CH2 P(C6H5)3; NaOH
10) PCC (an oxidant)
11) NaCN, H₂SO4
12) PhCH2CHO, H3O*
Propose the reaction mechanism for the two possible products formation from the following reaction of acetophenone and butanal using naoh.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.3 - Prob. 24.1PCh. 24.3 - Prob. 24.2PCh. 24.4 - Prob. 24.3PCh. 24.5 - Show how the following compound can be prepared...Ch. 24.5 - Prob. 24.5PCh. 24.5 - Prob. 24.6PCh. 24.6 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Treatment of cyclohexene with iodobenzene under...Ch. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - The aryl diene undergoes sequential Heck reactions...Ch. 24 - Heck reactions take place with alkynes as well as...Ch. 24 - Prob. 24.16PCh. 24 - The following transformation involves a series of...Ch. 24 - Show the sequence of Heck reactions by which the...Ch. 24 - Prob. 24.19PCh. 24 - Write the steps that are critical in the following...Ch. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Show how the following compound could be prepared...Ch. 24 - It is typically very difficult to do a...Ch. 24 - The compound eutypine is an antibacterial agent...Ch. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - The following transformation can be accomplished...Ch. 24 - Prob. 24.35PCh. 24 - Prob. 24.36PCh. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - E. J. Coreys 1964 total synthesis of...Ch. 24 - Prob. 24.40P
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