Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Question
Chapter SRP, Problem 22P
Interpretation Introduction
Interpretation:
A stereoselective synthesis of methyl trans-4 isopropyl cyclohexanecarboxylate is to be outlined from phenol.
Concept Introduction:
Stereo selectivity is the property of
This arises due to difference in steric and electronic effects that leads to different products.
The efficiency of stereo selectivity lies totally with the stereochemistry of the products that are formed.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
how to synthesize 2-phenylclohexanone from cyclohexanone?
The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxide
For following substituted benzenes:
[1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3:
Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?
Chapter SRP Solutions
Organic Chemistry
Ch. SRP - 1. Arrange the compounds of each of the following...Ch. SRP - 2. Arrange the compounds of each of the following...Ch. SRP - Predict the final product from each of the...Ch. SRP - Prob. 4PCh. SRP - Write detailed mechanisms for each of the...Ch. SRP - Prob. 6PCh. SRP - Prob. 7PCh. SRP - Give stereochemical structures for compounds AD:Ch. SRP - Prob. 9PCh. SRP - The remaining steps in the industrial synthesis of...
Ch. SRP - Prob. 11PCh. SRP - Prob. 12PCh. SRP - Prob. 13PCh. SRP - Prob. 14PCh. SRP - 17. Show how you would modify the synthesis given...Ch. SRP - Prob. 16PCh. SRP - Give structures for compounds AD. Compound D gives...Ch. SRP - The tranquilizing drug meprobamate (Equanil or...Ch. SRP - Prob. 19PCh. SRP - 22. Outlined here is the synthesis of a central...Ch. SRP - 23. What are compounds A and B? Compound B has a...Ch. SRP - Prob. 22PCh. SRP - Prob. 26PCh. SRP - 28. Compound Y shows prominent IR absorption...Ch. SRP - Prob. 24PCh. SRP - Consider this reaction involving peracetic acid:...
Knowledge Booster
Similar questions
- Show how to convert carboxylic acids to other functional groups, and devisemultistep syntheses using carboxylic acids as starting materials and intermediates.Explain how acid chlorides are used as activated derivatives of carboxylic acidsarrow_forwardPropose a feasible synthesis for diphenylacetylene from bromobenzene. Draw the reaction scheme and briefly describe the reaction.arrow_forwardSynthesize 2-methylbutanoic acid from 2-methylbutene. Please provide all steps and reagents used.arrow_forward
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward2-Butene-1-thiol is one component of skunk spray. how would you synthesize this substance from methyl-2-butenoate? from 1,3-butadiene?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
- Propose a synthesis of the topical anesthetic cyclomethycaine from 4-hydroxybenzoic acid, 2-methylpiperidine, and any other necessary reagents. HN' + HO. НО Cyclomethycaine 4-Hydroxybenzoic acid 2-Methylpiperidinearrow_forwardReaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.arrow_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_forward
- 2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl p-methylcinnamate. Show how this alcohol could be synthesized (a) by an aldol condensation of butanal and (b) by a malonic ester synthesis starting with diethyl malonate.arrow_forwardThe following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forwardAs a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde? (b) What was the other product?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