Exam 15: Reactions of Aromatic Compounds

Based on your knowledge of electrophilic aromatic substitution,and assuming the furan ring of benzo[b]furan (shown)is activated toward electrophilic aromatic substituted more so than the benzenoid ring,predict the preferential position of attack of an electrophile,i.e.,does the electrophile E⁺ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 or 4 product in the electrophilic aromatic substitution of pyridine.

Which reagent(s)would you use to carry out the following transformation? toluene $\to$ benzoic acid

Based on your knowledge of electrophilic aromatic substitution,and assuming the pyrrole ring of indole (shown)is activated toward electrophilic aromatic substituted more so than the benzenoid ring,predict the preferential position of attack of an electrophile,i.e.,does the electrophile E⁺ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on pyrrole,i.e.,does the electrophile E⁺ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

The reaction of benzene with (CH₃)₃CCH₂Cl in the presence of anhydrous aluminum chloride produces principally which of these?

The major product(s)of the following reaction, would be:

What product would result from the following series of reactions,

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination?

The major product(s)of the following reaction, would be:

When two different groups are present on a benzene ring,the ___ generally determines the outcome of an EAS reaction.

Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide.Which resonance form contributes most to the overall resonance hybrid?

S_N1 solvolysis of C₆H₅CH=CHCH₂Cl in water produces:

Draw a mechanism that explains the formation of the following product in this Friedel-Crafts alkylation:

The electrophilic bromination or chlorination of benzene requires,in addition to the halogen:

Acid-catalyzed hydration of 1-phenyl-1-pentene gives 1-phenyl-1-pentanol almost exclusively; the other possible hydration product,1-phenyl-2-pentanol,is not detected at all.Explain clearly.

What would you expect to be the major product obtained from the following reaction?