Nucleophilic aromatic substitution provides one of the common methods for making phenols. (Another method is discussedin Section 19-17.) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic startingmaterial, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol (c) p-chlorophenol(d) m-cresol (e) p-n-butylphenol

Nucleophilic aromatic substitution provides one of the common methods for making phenols. (Another method is discussedin Section 19-17.) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic startingmaterial, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol (c) p-chlorophenol(d) m-cresol (e) p-n-butylphenol

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.60P: Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A....

See similar textbooks

Similar questions

Nucleophilic aromatic substitution provides one of the common methods for making phenols. (Another method is discussedin Section 19-17.) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic startingmaterial, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol
To synthesize trans-cinnamic acid from benzaldehyde (PhCHO) and acetic anhydride (Ac2O) under basic, refluxing conditions to exemplify the Perkin condensation. 1. Draw the complete chemical reaction to be carried out. 2. Provide a complete arrow-pushing mechanism for the synthesis of trans-cinnamic acid. 3. Briefly describe the role of water, Na2CO3, and HCl in the isolation of the product. Draw the structure of the product at basic pH (after Na2CO3 addition) and at acidic pH (after HCl addition).
Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.)m-Nitrobenzenesulfonic acid
Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.)p-Chlorobenzoic acid
Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.) m-Chlorobenzoic acid
The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
Nucleophilic aromatic substitution provides one of the common methods for making phenols. ) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases. (a) m-cresol (b) p-n-butylphenol
(17, 18, 5) Give the relative rates of reaction of the four carboxylic acid derivatives below with aqueous sodium hydroxide to give the sodium carboxylate salt.
Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Write equations to show that Step 6 can be brought about using either methanol or diazomethane (CH2N2) as a source of the -CH3 in the methyl ester.
Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.) 1-Bromo-3-nitrobenzene
1.Describe the ozonolysis of alkenes 2.one mole of a hydrocarbon(A) reacts with one mole of beomine giving a dibromo compound C5H10Br2.Substance A on treatment with cold dilute kMnO4 solution forms a compound C5C12O2(C5H12O2) on ozonolysis A,gives equimolar quantities of propanone and ethanol.Deduce the structure of substance A.
Starting with benzene, outline a procedure for synthesizing m-chloroaniline.