Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
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.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Identify A, B, and C, intermediates in the synthesis of the five-membered ring called an α- methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.
The following set of reactions convert phenylacetylene to butylbenzene.
Give the appropriate reagents for each step of the following reaction sequence.
The acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be
visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid
conditions, and decarboxylation.
Br
H₂C
H3C
1. NaOEt
2. H₂O*
3. heat
H₂C.
OEt
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
H
X
CO2
CH3
+
EtOH
:OH
На
CH3
CO2
CH3
CH3
CH3
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardTreatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardOne step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.arrow_forward
- Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.arrow_forwardThe acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7barrow_forwardEsters can be prepared by the reaction of carboxylic acids with alcohols. Bearing this in mind, propose a route to the preparation of γ-Butyrolactone, the structure of which is shown below.arrow_forward
- The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.arrow_forwardComplete 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*arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License