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?

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?

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.48P: The Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following...

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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. a. Explain why none of the (trifluoromethyl)benzene reacts b. 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
Arrange the compounds in order of INCREASING reactivity towards bromination. I. Toluene, Nitrobenzene, Iodobenzene, Acetanilide II. Phenol, Acetophenone, Anisole, Chlorobenzene III. Aniline, Benzaldehyde, Benzonitrile, Benzenesulfonic acid
Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition-elimination mechanism.a. chlorobenzene, p-uoronitrobenzene, m-uoronitrobenzeneb. 1-fluoro-2,4-dinitrobenzene, 1-fluoro-3,5-dinitrobenzene, 1-fluoro-3,4-dinitrobenzenec. 1-fluoro-2,4-dinitrobenzene, 4-chloro-3-nitrotoluene, 4-fluoro-3-nitrotoluene
The Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following are two reactions intended to give benzyl tert-butyl ether. One reaction gives the ether in good yield, and the other reaction does not. Which reaction gives the ether? What is the product of the other reaction, and how do you account for its formation?
SN2 Reaction lodide ion is an effective nucleophile in S2 displacements. In acetone solution, other alkyl halides can be converted to alkyl iodides: CH;CH2 CH,CH3 I-C H;C H acetone X- Na I- H CH3 Na X X-Clor Br TR) Although you might expect such a reaction to be reversible, it can be made to proceed in the forward direction by using anhydrous acetone as the solvent because sodium iodide is soluble in this solvent, but sodium chloride and sodium bromide are not. We can detect whether a reaction has occurred by the formation of a precipitate of sodium chloride or bromide.
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
Arrange the compounds in order of INCREASING reactivity towards bromination. 1. Toluene, Nitrobenzene, Anisole, Aniline 2. Acetanilide, Benzaldehyde, Toluene, Iodobenzene 3. Acetophenone, Bromobenzene, Aniline, Phenol
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 nitration of benzoic acid gives almost exclusively 1,3-nitrobenzoic acid. By drawing the appropriate resonance forms of the intermediate cations resulting from attack of [NO2]+, explain this result.
Select from the Table provided the reagent you would use to carry out each of the transformations below. Reagents Available а. КОН e. Hg(OAc)2, H20; then NaBH4 i. O3; then Zn, H3O* b. KMNO4, H3O* f. Os04; then NaHSO3 j. H2SO4 с. На, Pd g. BH3; then H,O2, "OH k. Cl2 d. CH212, Zn(Cu) h. CHCI3, КОН I. CI CO,H , then H30* HO ? ? OH H3C- H3C- H3C H3C
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Draw the structure(s) of the major organic product(s) of the following reaction. H,C. 1. NaOCH3 / CH3OH 2. 1 eq. 2-bromo-2-methylpropane • You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr)2. • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu.