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Disclaimer: This post might be hard to read for some people. Some may even consider this a rant. You have been warned. This answer will question the validity of the used models, as well as the basis for such exercises. (It will also point to a fundamental flaw of this specific exercise.) If you are a student, you might learn concepts that will later turn out ...


3

Your reasoning is correct, but I think you'd mistakenly compared the ring strain of the rings, while I would have compared the ring strain in the corresponding ketones. Note that, you are asked about the stability of gem-diols, which could convert into the corresponding ketone. The point is, the ring isn't going to change, so the stability of rings don't ...


2

@ Martin has addressed the shortcomings of assessing “stability” by counting hyperconjugating C-H bonds. If by “more stable” one means which one of the two isomers, 1,2,3,4,5,8-hexahydronaphthalene 1 or cis-1,4,4a,5,8,8a-hexahydronaphthalene 2, has the lower heat of combustion, formation or hydrogenation, then a decision can be made. Unfortunately, there ...


1

A table of A-values indicate that $\ce{Br}$ substituent on a long chain organic molecule has relatively less steric effect than that of $\ce{Me}$- or $\ce{Et}$-group ($1.7$ and $\pu{1.75 kcal mol-1}$, respectively compared to $\pu{0.38 kcal mol-1}$ for $\ce{Br}$), and even smaller than that of $\ce{Cl}$ ($\pu{0.43 kcal mol-1}$), probably due to longer $\ce{C-...


1

Tl, dr: It's not just a matter of size. A combination of coordination geometry, node distribution in the $d$-orbital wavefunctions, and atomic size all conspire to weaken $\pi$ overlap in palladium and platinum carbonyls, not only relative to the nickel compound but also relative to earlier transition metal carbonyls in their respective periods. Ziegler et ...


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