Question

Geraniol (1) is found in rose oil and other plant extracts and is used commercially in fruit flavorings. It is also produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives POH 1. Draw structures of the expected products formed when Reraniol is reacted with ozone followed by reductive workup (Zn/H* or SMez). 2. Draw the structure of the expected major product formed when geraniol is treated with m-CPBA followed by dry HBr. How many stereoisomers will form? 3. Draw structures for the major product(s) of each reaction. Show stereochemistry when relevant. NBS, hv 1) 02 2) Zn°/H:0* HBT 1) BH 2) H20/OH OsO/H20 Br2, H2O m-CPBA 1) Hg(OAC), H20 2) NaBH

Answer 1

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