UTA Exam 2 Practice Additional Synthesis Practice - Fall 2020 9, Propose a forward synthesis of the following molecule from any precursors as long as they contain 4 carbons or less. You may use retrosynthetic techniques but your final answer must be the forward synthesis. Solvents are excluded from the 4 carbons rule. *Special directions for 9C. If you are absolutely stuck, consult the hints below as a last resort, but try your best to think of it yourself since that’s the most effective way to learn. OH OHHints: c. HO, i. NOTE: For C, you must start with 1-bromocyclohexane. All other precursors for this synthesis must be 4 carbons containing or less. Don't worry about stereochemistry for this example. ‘We can only use 4 carbon precursors, so we must use a technique to make C-C bonds. Can you see how to portion out your 2 reactants for a reaction with an organometallic reagent? That's a lot of carbons, we might have to use 2 separate organometallics to get this entire molecule together. We have an SP3 carbon with an OH and a cyclopropane, which indicates where the first step in the forward directions C=O group (to be reacted with an organometallic) should go. Br This is what 1-bromocyclohexane looks like. To make grignard reactions occur to form C-C bonds, we need a C=O. Well, we can oxidize secondary OH groups, but we have a Br here. If only we could substitute Br for OHPossible forward syntheses Note: | show different ways of using grignards. The most important part is using a suitable solvent (Et2O or THF are the most popular) and making sure the grignard + solvent is reacting ina different step than the workup (this would destroy the grignard). You may choose to show this with two separate steps (first grignard attack and second the protonation of the oxyanion). Another is to write the conditions for your grignard reaction and write the words “and then, work up.” Another is to use numbers, for example, “1: R-MgBr in THF/Et20. 2: work up" over one arrow. A* The text says: “in any polar protic solvent for SN1” Here is a synthesis involving SN1. If you're thinking this reaction is not the most efficient, you would be correct since the rate is far slower with secondary carbons instead of tertiary. Nevertheless, having a polar protic solvent with a “weak” nucleophile like H2O would favor SN1 enough to have this reaction proceed. If Professor Floreancig says you don't need to indicate solvents, | would recommend not putting solvents if you're unsure of their effects. | have here “in any polar protic solvent for SN1” for emphasis that you can choose whichever as long as its properties align with SN1 favorable conditions. Indeed, a racemic mixture would form but is not important here because both isomers will be oxidized by Pcc.