ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22.17, Problem 20P
Interpretation Introduction
Interpretation:
The proper sequence of synthetic transformationsin the conversion of benzene to
Concept Introduction:
>The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution, an electron rich species attacks the species that is deficient in electrons.
>The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate, which results in the removal of leaving group from the substrate.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Bupropion, sold under the trade name of Zyban, is an antidepressantthat was approved to aid smoking cessation in 1997. Devise a synthesisof bupropion from benzene, organic compounds that have fewer thanfive carbons, and any required inorganic reagents.
β-Vetivone is isolated from vetiver, a perennial grass that yields a variety of compounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process:Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (See Problem 23.61 for another method to form the bicyclic ring system of β-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.
Devise a synthesis of compound A from the given starting materials. Youmay use any other inorganic reagents or organic alcohols. A was used toprepare aliskiren, a drug used to treat hypertension
Chapter 22 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.4 - Prob. 5PCh. 22.4 - Prob. 6PCh. 22.4 - Prob. 7PCh. 22.4 - Prob. 8PCh. 22.4 - Prob. 9PCh. 22.7 - Prob. 10P
Ch. 22.8 - Problem 22.11 Three of the following amines can be...Ch. 22.9 - Prob. 12PCh. 22.10 - Prob. 13PCh. 22.13 - Prob. 14PCh. 22.14 - Prob. 15PCh. 22.15 - Prob. 16PCh. 22.15 - Prob. 17PCh. 22.17 - Prob. 18PCh. 22.17 - Prob. 19PCh. 22.17 - Prob. 20PCh. 22.17 - Prob. 21PCh. 22.18 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Arrange the following compounds or anions in each...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - The compound shown is a somewhat stronger base...Ch. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Write the structure of the product formed on...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - Devise efficient syntheses of each of the...Ch. 22 - Prob. 46PCh. 22 - Prob. 47PCh. 22 - Prob. 48PCh. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - Prob. 52PCh. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56DSPCh. 22 - Prob. 57DSPCh. 22 - Prob. 58DSPCh. 22 - Prob. 59DSPCh. 22 - Synthetic Applications of Enamines The formation...Ch. 22 - Prob. 61DSP
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
- Devise a synthesis of muscalure, the sex pheromone of the common housefly, from acetylene and any other required reagents.arrow_forwardBupropion, sold under the trade name of Zyban, is an antidepressant that was approved to aid smoking cessation in 1997. Devise a synthesis of bupropion from benzene, organic compounds that have fewer than five carbons, and any required inorganic reagents.arrow_forwardDevise a synthesis of compound A from the given starting materials. You may use any other inorganic reagents or organic alcohols. A was used to prepare aliskiren, a drug used to treat hypertension (see also Problem 5.7).arrow_forward
- Devise a synthesis of muscalure, the sex pheromone of the common housey, from acetylene and any other required reagents.arrow_forwardDraw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug pitavastatin, marketed in Japan as a calcium salt under the name Livalo.arrow_forwardWhat product is formed when A is treated with Grubbs catalyst underhigh-dilution conditions? This reaction was a key step in the synthesis ofstemoamide, the naturally occurring amide described in the opening paragraph.arrow_forward
- Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).arrow_forwardOne step in the synthesis of the antihistamine fexofenadine involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forwardMuscalure, the sex pheromone of the common housefly, can be preparedby a reaction sequence that uses two nucleophilic substitutions. Identifycompounds A–D in the following synthesis of muscalure.arrow_forward
- Carboxylic acid X is an intermediate in the multistep synthesis ofproparacaine, a local anesthetic. Devise a synthesis of X from phenoland any needed organic or inorganic reagents.arrow_forwardIdentify C and D in the following reaction scheme, two steps in the synthesis of the cholesterol-lowering drug atorvastatin (trade name Lipitor).arrow_forwardDraw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY