Chapter 5: Problem 7
Draw structural formulas for the other two stereoisomers of 2,4 -heptadiene.
Chapter 5: Problem 7
Draw structural formulas for the other two stereoisomers of 2,4 -heptadiene.
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Get started for free\( \alpha\)-Santonin, isolated from the flower heads of certain species of Artemisia, is an anthelmintic (meaning against intestinal worms). This terpene is used in oral doses (a) Locate the three isoprene units in santonin and show how the carbon skeleton of farnesol might be coiled and then cross-linked to give santonin. Two different coiling patterns of the carbon skeleton of farnesol can lead to santonin. Try to find them both. (b) Label all chiral centers in santonin. How many stereoisomers are possible for this molecule? (c) Calculate the index of hydrogen deficiency for santonin.
Trans-cyclooctene has been resolved, and its enantiomers are stable at room temperature. Trans-cyclononene has also been resolved, but it racemizes with a half-life of \(4 \mathrm{~min}\) at \(0^{\circ} \mathrm{C}\). How can racemization of this cycloalkene take place without breaking any bonds? Why does trans- cyclononene racemize under these conditions but trans-cyclooctene does not?You will find it especially helpful to examine the molecular models of these cycloalkenes.
Nepetalactone is the active ingredient of catnip. It is isolated as an oil from the plant Nepata cataria. Show that it is a terpene (i.e., that its carbon skeleton can be divided into isoprene units). Is the molecule chiral? How many stereoisomers are possible?
Following are lengths for a series of \(\mathrm{C}-\mathrm{C}\) single bonds. Propose an explanation for the differences in bond lengths. \begin{tabular}{|lc|} \hline Structure & Length of \(\mathrm{C}-\mathrm{C}\) Single Bond \((\mathrm{pm})\) \\ \hline \(\mathrm{CH}_{3}-\mathrm{CH}_{3}\) & \(153.7\) \\ \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{3}\) & \(151.0\) \\ \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}\) & \(146.5\) \\ \(\mathrm{HC} \equiv \mathrm{C}-\mathrm{CH}_{3}\) & \(145.9\) \\ \hline \end{tabular}
Bromine adds to cis- and trans-2-butene to give different diastereomers of 2,3
-dibromobutane. What does this say about the mode of addition of bromine to
this alkene?
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