Interpretation:
Using the resonance structures of the potential intermediates, the position and the ring in which nitration of 4-bromobiphenyl is expected to occur is to be stated and explained.
Concept introduction:
In
Resonance structures differ only in the position of the lone pair of electrons and those present in π bonds. There is no change in the position of atoms in the different forms. Curved arrows are used to represent the shift of the electrons. The actual structure of the compound is a hybrid of all possible forms. The stability of a resonance hybrid depends on the number of stable resonance forms that contribute to the actual structure.
To state and explain:
Using the resonance structures of the potential intermediates the position and the ring in which nitration of 4-bromobiphenyl is expected to occur.
Trending nowThis is a popular solution!
Chapter 16 Solutions
Organic Chemistry
- p-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?arrow_forwardPropose a feasible synthesis for diphenylacetylene from bromobenzene. Draw the reaction scheme and briefly describe the reaction.arrow_forwardWhen 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_forward
- The reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin. Write down the reaction mechanisms of these reactions and explain why.arrow_forwardWrite the etherification reactions of isopropyl bromide and 2-bromo-1-nitropropane with phenol . Which reaction takes place faster and why?arrow_forwardDescribe which products will be formed as a result of the reaction with nitronium ion in the electrophilic aromatic substitution reaction by drawing the structures of the compounds given below.a) methoxybenzene,b) benzoic acidarrow_forward
- The reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin production. Write down the reaction mechanisms of these reactions and explain why.arrow_forwardThe nitro groups on the benzene ring in the reactant serve two purposes.One is to let you know what atoms in the reactant correspond to what atomsin the product. But what role do the nitro groups play electronically – whywould the reaction be much slower if these nitro groups weren’t attached tothose benzene carbons? Draw any relevant structures to support youranswer.arrow_forwardFuran 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_forward
- List at least three (3) physical or spectroscopic methods that can be used to differentiate between benzophenone and benzhydrol. Explain how you would differentiate them. What are the most likely impurities to be found in the product of benzhydrol synthesis? How will they affect performance? How can its presence in the final product be reduced?arrow_forwardRank the compounds in order of increasing reactivity in electrophilic aromatic substitution. Briefly explain your answer. CóH5OH, C6H5SO3H, C6H5CIarrow_forwardDiphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY