Chapter 16: Q64E (page 524)
How would you synthesize the following substances starting frombenzene?
(a)

(b)

(c)

Short Answer
(a)
Synthesis of compound (a)
(b)
Synthesis of compound (b)
(c)
Synthesis of compound (c)
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Chapter 16: Q64E (page 524)
How would you synthesize the following substances starting frombenzene?
(a)

(b)

(c)

(a)
Synthesis of compound (a)
(b)
Synthesis of compound (b)
(c)
Synthesis of compound (c)
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Question: When benzene is treated with , deuterium slowly replaces all six hydrogens in the aromatic ring. Explain.
Draw resonance structures for the intermediates from the reaction of an electrophile at the ortho, meta, and para positions of nitrobenzene. Which intermediates are most stable?
Question: Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. The of unsubstituted phenol, for example, is 9.89, while that of p-nitrophenol is 7.15. Draw resonance structures of the corresponding phenoxide anions and explain the data.
Rank the compounds in each group according to their reactivity toward electrophilic substitution.
Starting with either benzene or toluene, how would you synthesize the
following substances? Assume that ortho and para isomers can be
separated.
(a) 2-Bromo-4-nitrotoluene (b) 1,3,5-Trinitrobenzene
(c)2,4,6-Tribromoaniline (d)m-Fluorobenzoic acid
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