Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 11.3, Problem 9P
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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.
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 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.
Explain why maleic anhydride reacts rapidly with 1,3-butadiene but does not react at all with ethene under thermal conditions.
Chapter 11 Solutions
Organic Chemistry - Standalone book
Ch. 11.1 - Prob. 1PCh. 11.1 - Prob. 2PCh. 11.2 - The two compounds shown differ by a factor of 60...Ch. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.2 - Prob. 6PCh. 11.3 - Prob. 7PCh. 11.3 - Prob. 8PCh. 11.3 - Evaluate 2,3,3-trimethyl-1-butene as a candidate...Ch. 11.4 - After heating a solution of allyl tert-butyl...
Ch. 11.5 - Prob. 11PCh. 11.6 - Prob. 12PCh. 11.8 - Prob. 13PCh. 11.9 - What dienes containing isolated double bonds are...Ch. 11.10 - Prob. 15PCh. 11.10 - Prob. 16PCh. 11.11 - Prob. 17PCh. 11.12 - Dicarbonyl compounds such as quinones are reactive...Ch. 11.12 - 2,3-Di-tert-butyl-1,3-butadiene is extremely...Ch. 11.12 - Methyl acrylate (H2C=CHCO2CH3) reacts with...Ch. 11.13 - Prob. 21PCh. 11.14 - What diene and dienophile could you use to prepare...Ch. 11.14 - Write equations in the synthetic direction for the...Ch. 11.16 - Prob. 24PCh. 11.16 - Prob. 25PCh. 11 - Write structural formulas for each of the...Ch. 11 - Give an acceptable IUPAC name for each of the...Ch. 11 - A certain species of grasshopper secretes an...Ch. 11 - Which of the following are chiral?...Ch. 11 - Describe the molecular geometry expected for...Ch. 11 - Prob. 31PCh. 11 - What compound of molecular formula C6H10 gives...Ch. 11 - Prob. 33PCh. 11 - Prob. 34PCh. 11 - Prob. 35PCh. 11 - Prob. 36PCh. 11 - Identify the more reactive dienophile in each of...Ch. 11 - Prob. 38PCh. 11 - Prob. 39PCh. 11 - Prob. 40PCh. 11 - Prob. 41PCh. 11 - Prob. 42PCh. 11 - Prob. 43PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Show how to prepare each of the following...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Compound A was converted to compound B by the...Ch. 11 - Suggest reasonable explanations for each of the...Ch. 11 - Prob. 53PCh. 11 - Prob. 54PCh. 11 - Prob. 55DSPCh. 11 - Prob. 56DSPCh. 11 - Prob. 57DSPCh. 11 - Prob. 58DSPCh. 11 - Prob. 59DSP
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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?arrow_forwardExplain why the ratio of reactants of Nitration of Bromobenzene and reactants of friedel-crafts alkylation of p-Xylene with 1-Bromopropane are different.arrow_forwardWhat is the function of N-bromosuccinimide in allylic bromination reactions?arrow_forward
- Electrophilic nitration of benzoic acid gives almost exclusively 3-nitrobenzoic acid. By drawing the appropriate resonance forms of the intermediate cations resulting from attack of [NO2]+, explain this result.arrow_forward2-methoxypyrrole is brominated exhaustively by treatment with Br2, while 2-methoxypyridine is selectively brominated at the 5-position. Explain thedifferences in reactivity, and the regioselectivity of the pyridine bromination,using resonance structures as part of your explanation.arrow_forwardRank 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-nitrotoluenearrow_forward
- Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition-elimination mechanism. a. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene b. 1-fluoro-2,4-dinitrobenzene, 1-fluoro-3,5-dinitrobenzene, 1-fluoro-3,4-dinitrobenzene c. 1-fluoro-2,4-dinitrobenzene, 4-chloro-3-nitrotoluene, 4-fluoro-3-nitrotoluenearrow_forwardAnswer the following question pertaining to the reaction of maleic anhydride and 1,3-butadiene: Why does 1,3-butadiene react more rapidly with maleic anhydride than with another molecule of itself?arrow_forward1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with(a) buta-1,3-dienearrow_forward
- What are the possible causes of low percentage yield in the preparation of tetraphenylcyclopentadienon using a reaction between benzil and dibenzyl ketonearrow_forwardIn the electrophilic aromatic substitution of toluene formation of 4-chlorotoluene is favored over 3-chlorotoluene. Explain this observation by writing the reaction mechanism.?arrow_forwardIn the synthesis of 1-phenylazo-2-naphthol (or Sudan I), phenyldiazonium reacts with β-naphthol. Draw the resonance structures of the intermediate formed when the diazonium ion attacks a) carbon 1 and b) carbon 3 of β-naphthol. Based on the resonance structures, explain why attack on carbon 1 is preferred.arrow_forward
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