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Exam 15: Reactions of Aromatic Compounds

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Question 81

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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?

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3-substitution is preferred,since this l...

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Question 82

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Which of these is a satisfactory synthesis of 1-bromo-2-phenylethane?

A) C₆H₅CH₂CH₃ + Br₂,Fe³⁺ -- $\rightarrow$
B) C₆H₅CH₂CH₃ + Br₂,400 $\degree$ C -- $\rightarrow$
C) C₆H₅CH₂CH₂OH + Br₂,CCl₄ -- $\rightarrow$
D) C₆H₅CH=CH₂ + HBr,ROOR -- $\rightarrow$
E) C₆H₅CH₂CH₃ + NBS,ROOR -- $\rightarrow$

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Question 83

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

Which of the following reactions would yield isopropylbenzene as the major product?

Consider the structures given below.Which of them would be a relatively stable contributor to the hybrid formed when toluene undergoes para bromination?

How might the following synthesis be carried out:

Which alkyl halide can undergo both S_N1 and S_N2 reactions in nonacidic solvents?

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

Which of the following reactions could be used to synthesize tert-butylbenzene?

When the following substance is treated with Br₂/FeBr₃,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring nitration?

Which of the following compounds would be least reactive toward electrophilic substitution?

Which is the best sequence of reactions for the following transformation?

Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

How might the following synthesis be carried out:

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

Which of the following structures would not be a contributor to the resonance hybrid of the benzyl cation?

What product would result from the following series of reactions,

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

This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.