Electrophilic bromination of an equimolar mixture of methylbenzene (toluene) and (trifluoromethyl)benzene with one equivalent of bromine gives exclusively 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene. Explain why none of the (trifluoromethyl)benzene reacts Explain the regiochemical outcome of the reaction In other words, why are 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene formed from the toluene?

Electrophilic bromination of an equimolar mixture of methylbenzene (toluene) and (trifluoromethyl)benzene with one equivalent of bromine gives exclusively 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene. Explain why none of the (trifluoromethyl)benzene reacts Explain the regiochemical outcome of the reaction In other words, why are 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene formed from the toluene?

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.47P: When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and...

See similar textbooks

Similar questions

When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.
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.
-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
In an aqueous solution containing sodium bicarbonate, aniline reacts quickly with bromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions, however, and the yields (mostly m-nitroaniline) are poor.Explain why nitration of aniline is so sluggish and why it gives mostly metasubstitution.
we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
Which set of reagents would be appropriate to synthesize bromobenzene from benzene? 1. HNO3 in H2SO4; 2. H2Cr04 and heat 1. H2CrO4 and heat; 2. H2 Pd/C Br2 and FeBr3 1. CH3CH2CHCI and AICI3; 2. H204 and heat 4B12 and Fe Heat and Br2 Br2, HCI
Q1/ Do as required: 1- The role of HSO, in Preparation of Nitrobenzene. Explain 2- The using of NaOH with 2-naphthol in preparation of azo dye? 3- Preparation of Nitrobenzene in cool phase. 4- Adding HCI in the preparation of aniline from nitrobenzene. 5- When acetanilide reacts with bromine (x), acetanilide gives p-bromo acetanilide only, why? 6- In an experiment Hydrolysis of Acetanilide What color does the litmus naner
Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran. Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.
Electrophilic bromination of an equimolar mixture of methylbenzene (toluene) and (trifluoromethyl)benzene with one equivalent of bromine (in the presence of FeBr3) gives exclusively 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene. 1. Explain why none of the (trifluoromethyl)benzene reacts 2. Explain the regiochemical outcome of the reaction In other words, why are 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene formed from the toluene?
Provide the reagents necessary to carry out the conversion shown. H₂O/H₂SO4, PCC/CH₂Cl₂ CPCC/ CH₂Cl₂ 9-BBN: H₂O₂/NaOH/H₂O O: Zn/acetic acid 9-BBN: H₂O2/NaOH/H₂O: CrO:/H₂SO/H₂O O H
Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition–eliminationmechanism. 1-fluoro-2,4-dinitrobenzene, 4-chloro-3-nitrotoluene, 4-fluoro-3-nitrotoluene
Alkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzene