(-)-Cameroonanol has been isolated from the essential oil of Echinops giganteus

Question

(-)-Cameroonanol has been isolated from the essential oil of Echinops giganteus (globe thistle) plants and it is associated with a strong woody fragrance. Its structure, including relative stereochemistry, was confirmed when it was made in the laboratory according to the sequence shown below. Recall that a C-c bond is made up of one sigma bond and one pi bond. These two bonds together have a combined BDE (bond dissociation energy) of 607 kl/mol. Use this information, together with the data in Table 6.1, to estimate the H° for the conversion of compound 1 into compound 2. Br OH two steps H hv --Cameroonanol kJ/mol

Explanation / Answer

The enthalpy of reaction = sum of bond energies of reactants - sum of bond energie so products

Here we have one double bond in the reactant

while in case of product we have one C-C bond, One C-H bond and one C-Br bond

deltaHrxn = (B.E C=C) - (B.E H-C + B.EC-C + B.EC-Br)

DeltaHrxn = 607 - (397 + 356 + 285) = -431 kJ / mole

[The answer may vary considering the source of bond energies used as the table is not provided)

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