Concept explainers
Interpretation:
The observation that Friedel-Crafts alkylations often give polysubstituted products but Friedel-Crafts acylations do not is to be explained.
Concept introduction:
Friedal-Crafts reaction is an electrophilic substitution reaction in which an
To explain:
The observations that Friedel-Crafts alkylation reactions give polysubstituted products but Friedel-Crafts acylations do not.
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Chapter 16 Solutions
Organic Chemistry
- 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.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_forwardGive the products of the following substitution reactions. For every reaction, show electron pairs on both nucleophile and leaving group.arrow_forward
- When bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.arrow_forwardExplain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardThe Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?arrow_forward
- Describe the product formed as a result of the reaction between cyclohexanone and 3-butene-2-one by also writing the mechanism of the reaction.arrow_forwardThe carbocation electrophile in a Friedel-Crafts reaction can be generated in ways other than by reaction of an alkyl chloride with AlCl3. For example, reaction of benzene with 2-methylpropene in the presence of H3PO4 yields tert-butylbenzene. Draw a structure for the electrophile.arrow_forwardHow does the reactivity of an aldehyde or a ketone toward nucleophiles compare with thereactivity of the carbonyl compounds whose reactions you studied in Chapter 15?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning