"My first session with the student was spent primarily on arrow pushing mechanisms for a variety of different reactions. We spent the first ten minutes or so discussing what specifically the student was struggling with and what she felt more confident in. For the most part, the student seemed to only feel good when it came to nomenclature, so we started in on reviewing problems from some of the worksheets her professor had posted. The first reaction we went over was an E2 reaction, which the student didn't seem to know much about. I discussed the three important factors to consider in elimination reactions with her (strength of leaving group, carbocation stability, and base strength) to help clarify why it was E2 and not E1. I walked her through the first mechanism to show her why the arrows went certain ways and what each arrow actually indicated before letting her try a similar problem with her walking me through the steps. Since it was our first session, she was a little shaky on what I wanted her to do, but we eventually got through the problem with a good amount of success. We then went through an E1 reaction to compare them, which seemed helpful to the student. The other reaction mechanisms we approached in the same format covered reductive ozonolysis, a two-step E2 and hydrogenation, and alcohol dehydrogenation. I really tried to stress core concepts to the student as well as arrow pushing mechanisms, having her draw Lewis dot structures, calculate formal charges, define Lewis acids and bases, and judge the strength of leaving groups. So far, my biggest concern for the student is her shakiness on fundamentals, which makes mechanisms and synthesis (her two big areas of concern) much harder to grasp. She had a couple of worksheets from her teacher to do and a table summarizing the main reactions they have to know that she said she was going to try and do before our next session tomorrow."