검증된 단계별 안내
06:38
05:
05:09In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]
(b) This reaction sequence was used in the synthesis of (+) -lineatin, a monoterpene aggregation pheromone from the female ambrosia beetle Trypodendron lineatum (Org. Lett. 2004, 6, 1449–1452).
When using sulfuric acid, but in the absence of other nucleophiles like water or bromide ion, less stable alkenes can be isomerized to their more stable isomer. Provide a mechanism for these acid-catalyzed isomerization reactions. [This is one illustration of the principle of microscopic reversibility.]
(b)
A common situation occurs when both carbons of the mercurinium ion are secondary. In a situation like the one shown, to which carbon would you expect water to add? That is, would you expect to produce A or B? Explain your answer.
When using sulfuric acid, but in the absence of other nucleophiles like water or bromide ion, less stable alkenes can be isomerized to their more stable isomer. Provide a mechanism for these acid-catalyzed isomerization reactions. [This is one illustration of the principle of microscopic reversibility.]
(c)
Predict the product of each of the following hydroboration–oxidation or oxymercuration–reduction reactions used in the modern synthetic organic chemistry literature (modified to use reagents we are used to seeing).
(c) A similar sequence was featured in the synthesis of muricadienin, a proposed precursor in the biosynthesis of solamin (Org. Lett. 2014, 16, 5886–5889).
If you react carvone with a single equivalent of HBr, only one product is produced, even though carvone has two carbon–carbon double bonds. Explain this observation.
