Chapter 10: Q47E (page 308)
How might you use a Suzuki–Miyaura reaction to prepare the biarylcompounds below? In each case, show the two potential reactionpartners.
Short Answer
(a)
(b)
(c)
Chapter 10: Q47E (page 308)
How might you use a Suzuki–Miyaura reaction to prepare the biarylcompounds below? In each case, show the two potential reactionpartners.
(a)
(b)
(c)
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Get started for freeAlkylbenzenes such as toluene (methylbenzene) react with NBS to give
products in which bromine substitution has occurred next to the aromatic ring (the benzylic position). Explain, based on the bond dissociation energies in Table 6-3 on page 170.
Draw structures corresponding to the following IUPAC names: (d) cis-1-Bromo-2-ethylcyclopentane
Draw the electron-pushing mechanism for the propagation steps of the allylic bromination reactions below. You may omit NBS in your mechanism, and use Br∙ and Br2.
(b)
Choose the alcohol from each pair below that would react faster withHX to form the corresponding alkyl halide.
Question: Why do you suppose it’s not possible to prepare a Grignard reagentfrom a bromo alcohol such as ? Give another exampleof a molecule that is unlikely to form a Grignard reagent.
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