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The compound shown below is a volatile oil isolated from pine needles. Show the major product of the reaction of this compound with the

The compound shown below is a volatile oil isolated from pine needles. Show the major product of the reaction

The compound shown below is a volatile oil isolated from pine needles. Show the major product of the reaction of this compound with the following reagents: (a) H/Pd-C (b) OsO, followed by hydrogen peroxide (c) Diborane in THF, followed by H2O in NaOH (d) Hg(OAc)2 in water, followed by NaBH4 (e) Ozone followed by workup with dimethyl sulfide (f) m-cloroperoxybenzoic acid followed by treatment with strongly acidic aqueous solution. Explain, with reference to the structure why a single major product would predominate in reactions b, c, and f though more may be chemically feasible (think about steric issues).

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