Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 23, Problem 25P
Interpretation Introduction
Interpretation:
The missing reagents and the structure of compound A in the synthesis of tamoxifen are to be determined.
Concept introduction:
The grignard reagent is prepared by the reaction of alkyl or aryl bromide with magnesium metal in the presence of ether.
The reaction of the grignard reagent with an
Oxidation reaction involves an increase in the
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Outline a synthesis for the following transformation and provide a justification for your chosen strategy. (More than one steps may be required)
Cancer of the prostate is the second leading cause of cancer deaths among American males, exceeded only by lung cancer. One treatment of prostate cancer is based on the fact that testosterone and androsterone (both androgens) enhance the proliferation of prostate tumors. The drug flutamide (an antiandrogen) reduces the level of androgens in target tissues and is currently used to prevent and treat prostate cancer.Propose a synthesis of flutamide from trifluoromethylbenzene
Diazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed, diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the 2° amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous NaOH followed by careful acidification with HCl.
Q. Is diazepam chiral? If so, how many of the possible stereoisomers are formed in this synthesis?
Chapter 23 Solutions
Organic Chemistry - Standalone book
Ch. 23.1 - Prob. 1PCh. 23.3 - Problem 23.2 One of the hydroxybenzoic acids is...Ch. 23.4 - Prob. 3PCh. 23.5 - Prob. 4PCh. 23.6 - Problem 23.5 The compound shown was required for...Ch. 23.8 - Prob. 6PCh. 23.8 - Prob. 7PCh. 23.9 - Prob. 8PCh. 23.9 - Prob. 9PCh. 23.10 - Prob. 10P
Ch. 23.12 - Prob. 11PCh. 23 - The IUPAC rules permit the use of common names for...Ch. 23 - Prob. 13PCh. 23 - Prob. 14PCh. 23 - Prob. 15PCh. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 23 - Prob. 18PCh. 23 - Prob. 19PCh. 23 - Prob. 20PCh. 23 - Prob. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Choose the reaction in each of the following pairs...Ch. 23 - Pentafluorophenol is readily prepared by heating...Ch. 23 - Prob. 29PCh. 23 - Treatment of p-hydroxybenzoic acid with aqueous...Ch. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Treatment of 2,4,6-tri-tert-butylphenol with...Ch. 23 - Prob. 34PCh. 23 - Prob. 35PCh. 23 - Prob. 36DSPCh. 23 - Prob. 37DSPCh. 23 - Prob. 38DSPCh. 23 - Prob. 39DSP
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 widely used anticoagulant warfarin (see Chemical Connections: From Moldy Clover to a Blood Thinner in Chapter 18) is synthesized from 4-hydroxycoumarin, benzaldehyde, and acetone as shown in this retrosynthesis. Show how warfarin is synthesized from these reagents.arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardDiazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed, diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the 2° amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous NaOH followed by careful acidification with HCl. Q.Given this retrosynthetic analysis, propose a synthesis for diazepamarrow_forward
- Methamphetamine is a long-lasting, potent stimulant sold as a street drug. The synthesis is quite simple and one step in the synthesis is shown below. Using your knowledge of the reactions of amines, provide all the reagents necessary to complete the reaction below. Provide the reagents for step 1 and step 2 ,arrow_forwardPropose the structure of a starting material that would allow you to use the procedures given to synthesize acetaminophenarrow_forwardPrepare the following compound by the synthesis of malonic acidarrow_forward
- The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Show how this same synthetic strategy can be used to prepare ethosuximide and methsuximide.arrow_forward17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifenarrow_forward(A)Complete reaction between benzil and sodium borohydride to from benzoin b) complete reaction below between benzil and sodium borohydride to from hydrobenzoinarrow_forward
- Draw a complete arrow pushing mechanism for the specific Friedel Crafts acylation which involves the acylation of 1,3-benzodioxole using propionyl chloride as the acylating agent in the presence of zinc oxide nanoparticles as a catalyst. This reaction results in the formation of a propionylated product. The reaction is facilitated by the Lewis acid catalysis provided by zinc oxide nanoparticles.arrow_forwardProvide a mechanism for the following transformationarrow_forwardA certain compound is known to contain an aromatic benzene ring but failed to produce a fragrant yellow solution upon subjecting it to the nitration test. What may be a possible explanation for this? A. The benzene ring is part of a highly conjugated, blue dye molecule. B. The benzene ring contains a strong electron-withdrawing group. C. The benzene ring has no available sites left for electrophilic attack. D. All of the given. Kindly explain your answer in detail.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
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