Suggested+Experiments

=Suggested Experiments= 1. Heat 4-chlorobenzaldehyde in ethanol. Based on the behavior of heating 4-chlorobenzaldehyde in ethylene glycol (CRSEXP006) it may form an acetal in the absence of a catalyst. **[JC Bradley]** 2. Obtain the HNMR of water saturated with NaCl, octanoic acid saturated with brine and brine saturated with octanoic acid **[JC Bradley]** 3. The group at insilicomolecule has suggested the for making potentially pharmacologically active compounds while working under an open environment. This could be an interesting overlap with the CRS project because the key 3 steps involve SELECTIVE monoalkylation of a primary amine with 2 primary (methyl bromide and ethyl bromide and one secondary alkyl halide (cyclopropyl bromide). This of course is a notoriously difficult problem in organic syntheses (limiting the reaction to monoalkylation when the products are generally more nucleophilic than the starting primary amine). There a host of other problems like trying to not work with gasses, carcinogens, etc.. However, this initial suggestion by insilicomolecule does inspire some exploration of related 2 component systems: aldehydes and ketones (aromatic like benzaldehyde, others like acetone, butyraldehyde (perhaps trioxane) with primary (1-aminopropane, aniline) secondary (piperidine) and tertiary (triethylamine): obviously this would be a route to reductive amination (perhaps through formic acid). We also need to monitor the behavior of different kinds of amines to primary amines like 1-bromopropane - and the role of water - some amines only come conveniently in aqueous solution (like methyl amine). We have every chemical mentioned above in my lab at Drexel. There is a very good example of how organic chemists think about using carbonyl groups (aldehydes, ketones, carboxylic acids, esters, etc.) with alcohols and amines in the Wikipedia discussion of the synthetic approaches to physostigmine. Ultimately the product is an N,N-acetal but the discussion of how to get there involves using acetals as protecting groups (conditions for putting on and removing), monoalkylation of amines, stereochemistry control and many other issues related to the in silico molecule scheme linked above and our strong interest in these functional groups. There are surely an enormous number of "failed experiments" in the lab notebooks of the people involved in these syntheses that will never be disclosed. One key question for this Chemical Rediscovery Survey to answer is to what extent does revealing under Open Notebook Science conditions every detail of every chemical mixing change the way we think about chemistry. This is especially true if we are placing arbitrary barriers such as not using inorganics or catalysts of any kind. We have already discovered that even acetals (in addition to hemiacetals) do not require purposeful addition of a catalyst to form..**[JCB]** 4. In order to determine the large 1 ppm downfield shift of acetone (from Discovery3 ) there are many ways to approach this but here are the obvious quick experiments: use a regular (not co-axial) tube and add some acetone to D2O (make sure it is the same bottle!!) - that would explore the possiblity that size matters. Run acetone in the internal co-axial system again but with CDCl3 on the outside.