Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Question
Chapter 8, Problem 62P
Interpretation Introduction
Interpretation: The best route to form the target molecule A needs to be determined considering the prices of the starting materials.
Concept Introduction: The
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Ethers/Aldehydes/Ketones SynthesisDraw and Prepare the following compounds from any simple alkyl halide having four carbons or less,cyclohexane, and/or benzene. You may also use ethylene oxide (oxacyclopropane). SHOW ALLSTEPS AND REAGENTS with arrows.
Synthesis. Developments in medicine follows advances in synthetic
chemistry. Anyone that disagrees would perhaps be well served to
imagine the state of surgery if organic chemists had not developed local
anesthetics. The following structure is the free base of hexylcaine (1), a
local anesthetic developed by Merck. Propose a synthesis of 1 starting
(1)
from benzene and acyclic components containing five carbons or less. Justify any chemo-, regio- or
stereo selective steps in your synthesis. (
Chemistry
Provide reagents/conditions to accomplish the following syntheses. Several steps are required in some cases.
Chapter 8 Solutions
Organic Chemistry: Structure and Function
Ch. 8.1 - Prob. 8.1ECh. 8.1 - Prob. 8.2ECh. 8.3 - Prob. 8.4TIYCh. 8.3 - Prob. 8.5ECh. 8.3 - Prob. 8.6ECh. 8.4 - Prob. 8.7ECh. 8.5 - Prob. 8.8ECh. 8.5 - Prob. 8.9ECh. 8.5 - Prob. 8.10ECh. 8.5 - Prob. 8.11E
Ch. 8.5 - Prob. 8.12ECh. 8.6 - Prob. 8.14TIYCh. 8.7 - Prob. 8.15ECh. 8.7 - Prob. 8.16ECh. 8.8 - Prob. 8.18TIYCh. 8.8 - Prob. 8.19ECh. 8.8 - Prob. 8.21TIYCh. 8 - Prob. 24PCh. 8 - Prob. 25PCh. 8 - Prob. 26PCh. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Prob. 46PCh. 8 - Prob. 47PCh. 8 - Prob. 48PCh. 8 - Prob. 49PCh. 8 - Prob. 50PCh. 8 - Prob. 51PCh. 8 - Prob. 52PCh. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - Prob. 55PCh. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - Prob. 59PCh. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - Prob. 65PCh. 8 - Prob. 66P
Knowledge Booster
Similar questions
- Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases.arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.arrow_forwardDevise a synthesis of each of the following compounds. Besides inorganic reagents, you may use hydrocarbons and halides having ≤ 6 C′s, and CH2=CHCOOCH3 as starting materials. Each synthesis must use at least one of the carbon–carbon bond-forming reactions.arrow_forward
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forwardThe academic version of the process invention program (PIP) contains several examples, as follows: HDAl-hydrodealkylation of toluene to produce benzene CYHEXl-cyclohexane production by hydrogenation of benzene STYRl-styrene production from ethylbenzene XYLl-production of m-xylene from toluene ANHYDl-reaction of acetone and acetic acid to form acetic anhydride BUTALl-alkylation reaction of butene-1 and isobutane to produce iso-octane Select the “new plant design” mode and the “look at existing flow sheet” option, and follow the synthesis steps for one of these processes. ‘Obtain the current flow sheet as output at each level of the synthesis procedure. Also list the heuristics used at each step.arrow_forwardBenzoic acid, Ph-COOH (C6H5CO2H), is not soluble in water while it dissolves in ether (diethyl ether), (CH3CH2)2O. Yet upon treatment with sodium hydroxide, benzoic acid turns hydrophilic and dissolves in water. Provide chemical explanation of this observation.arrow_forward
- Syntheses of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short sequences of reactions that would be appropriate for each transformation. (a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanonearrow_forwardWhich of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4arrow_forwardDevise a synthesis of 1-phenyl-5-methylhexane [C6H5(CH2)4CH(CH3)2] from acetylene, alkyl halides, and any required inorganic reagents.arrow_forward
- Provide reagents/conditions to accomplish the following syntheses.arrow_forwardProvide reagents/conditions to accomplish the following syntheses. Several steps are required in some cases.arrow_forward3. An alcohol containing natural product A (C10H200) that is a common ingredient in cough drops yields two structurally isomeric alkenes, 1 and 2, on dehydration. Ozonolysis followed by an oxidative workup or a reductive workup as shown yields 3 and 4 from 1 and 2, respectively. Hydroboration of alkene 1 yields the starting alcohol A as the major product from 1. Hydroboration yields a mixture of the starting alcohol A and a diastereomer of A starting from alkene 2. Given this information deduce the structure of A, 1, and 2. Show the correct absolute and relative stereochemistry for A (the alcohol group is cis to a methyl group), 1, and 2 and correctly name these three compounds. H2SO4 heat 1) O3 Н. 1 (C10H18) 2. Zn, H3O* 3 H. A (C10H200) H2SO4 1) O3 н СНО heat 2 (C10H18) 2. Zn, H3O* Н 4arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles 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 Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary 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