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Hi everyone. I had a question concerning the basicity of nitrogens in Imidazole ( 2 nitrogens) vs the basicity in the 1 nitrogen in Pyrrolidine. I understand that the nitrogen not attached to the hydrogen in Imidazole is the most basic of the 3 because of the lone pair that is in the same plane of the aromatic system. However, I was stuck on the LEAST basic nitrogen of the 3. I know the lone pair of second nitrogen in Imidazole is in the plane of the aromatic system, but not sure about the lone pair of the nitrogen in Pyrrolidine. Any help is greatly appreciated. Thanks!

Hi. I was wondering if someone can show me the synthesis of butyl isopropyl sulfide using 1-butanol, 2-propanol and any solvents/reagents. I tried treating 1-butanol with SOCl2 to form chlorobutane and 2-propanol with SOCl2 as well. I'm unclear onto how to get the sulfur connected to those 2 parts. I assume when that is accomplished, Mg in solvent can be used. Oxidizing agents like KMnO4 can be used and Zn(Hg), HCl as a reducing agent to remove the carbonyl at the end.. Any help is greatly appreciated!