Recall that this is how relative stabilities of alkenes were determined (Chapter 4). ↵ A longer version of this brief overview is found in Chapter 2. ↵ http://phototroph.blogspot.com/2006/...n-spectra.html ↵ Recall we saw this same tautomerism when water adds across a triple bond. ↵ https://en.Wikipedia.org/wiki/Gilman_reagent ↵ The explanation for this phenomenon goes beyond the scope of this course and is best explained using the theory of hard and soft acids and bases. For more information see https://en.Wikipedia.org/wiki/HSAB_theory ↵ This is in contrast to simple hydrocarbons which do not smell. In fact, methane thiol (\(\mathrm{CH}_{3}\mathrm{SH}\)) must be added to methane and propane which are used for heating so that they can be detected in the event of a gas leak. ↵ TNT is an explosive compound, as are many nitrated organic compounds (for example nitroglycerin). The nitro group is relatively unstable (\(\mathrm{NO}\) bonds are weak) and these compounds can decompose explosively to produce more stable nitrogen oxides and \(\mathrm{CO}_{2}\), releasing a great amount of energy at the same time. https://en.Wikipedia.org/wiki/Trinitrotoluene ↵ Except for the radical-induced addition of \(\mathrm{HBr}\) in an anti-Markovinkov manner across a double bond. ↵ Recall that there is some double bond character between carbons 2 and 3 and, therefore, rotation is somewhat restricted around this bond unlike a normal \(\mathrm{C-C}\) single bond.