Olah (1962)

What are the limits of what can and cannot be digested in acid? How chaotic can an acid bath get?

 

In Olah’s paper we will look at superacids, bored PhDs, the activation of saturated hydrocarbons, various organic cations and their condensation and fragmentation products.

 

Some things to think about before Monday’s discussion would be; what is the nature of a proton in a sea of molecules that want nothing to do with it? How does cation stability relate to structure for organic molecules? What is methanium and why have we not heard of it before? On Monday we will discuss these points.

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7 Responses to “Olah (1962)”

  1. Hunter Burgin Says:

    In regards to “scheme one” of Olah’s paper which shows the chemical reaction involving methane and the “magic acid” more commonly known as fluorosulfuric acid (FSO3H) I was interested to know what exactly is the fate of the hydrogen gas released in the reaction. The magic acid is such a strong base it can make a somewhat inert chemical such as methane act as a lewis base which leads to the cascade of events seen in scheme one which eventually releases H2 gas at several points. Does this released H2 gas serve as a reagent in further ensuing downfield reactions or is it just released as H2 gas as a byproduct in the reaction?

    • Adam Settimo Says:

      It says that the hydrogen gas can serve as a reducing agent to the acid and therefore must be swept away. Because of this, “the formation of H2 gas cannot be used to monitor the reaction progress.” Which made me curious about the why they could vacuum it off, sequester it somewhere else and measure it separately?

  2. Adam Settimo Says:

    My question has is quick and clean, what is going on in the last scheme? the very last step in which neutral (CH3)3CH is deprotonated into the trimethylcarbonium ion? We’re working in acid yet there’s something that is coming in and stripping off that H? is it like an equilibrium exchange between another trimethylcarbonium ion, like they’re joggling it back and forth?

  3. Porter Marsh Says:

    The paper talks about CH5+ and other carboniums but the H+ always seems to be on some carbon. Even in the super acid, is it ever the case that a free floating can exist in solution? When the magic acid reacts with a methane does it ever result in CH4 and an unbound H+, or only CH5+?

  4. Antony Says:

    I have a question on the final paragraph where they suggest that saturated hydrocarbons should not be referred to as paraffins but alkanes. Is he saying that its a misnomer because they are reactive and “parum affinis” refers to them being nonreactive? Are protonated alkanes useful at all in organic synthesis or are they too reactive? Could/are people using “magic acid” to sequester methane gas or make more “fossil fuels” synthetically?

  5. Daniel Begay Says:

    As it said in the paper, Scheme I is a clean cut version of what is actually going on. There are a lot of side reactions that lead to a variety of products such as ethyl cations, isopropyl cations etc. So I’m sure that discovering that methane, under the right conditions can be used in polycondensation, but it seems like the amount of side reactions and final products are unclear. As it states that the final products are described as “higher molecular weight hydrocarbons”. Do you think if you’re able to have controllable conditions, this would be a viable option in polymer chemistry? or is it too much of a wild card to be used for synthesis?

  6. Josh Ellsworth Says:

    I’m curious as to the chemical engineering required for these reactions. What are the materials used for the reaction flasks? Can super-acids protonate teflon? It seems that in theory these materials could be used to sequester methane from oil wells simply by passing the natural gas through a reaction chamber filled with super-acid. One could even use the excess Hydrogen generated to help power or pay for the process, and the newly generated carbocations could be neutralized by reacting them with the crude oil and getting a head start on the cracking process. This begs the question, could super-acid be separated from its alkane victims and regenerated, or is this a one off reaction?

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