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University of California - Irvine
J Freeman

Chem 51B, 2014 Prof. Zhibin Guan Chem 51B Midterm 1 Tuesday, February 4, 8:00 – 9:00 am Will cover Smith (4 Ed.) Chapters 9-12 (1 hr, closed book and notes, no calculator, molecular models are allowed in transparent plastic bag) Brief Study Guide of the Most Important Topics 1. Know how to name relatively simple compounds following IUPAC rules. 2. Know how to prepare the family of compounds covered in these three chapters, and understand their basic properties. 3. Given reactants and reaction conditions, be able to recognize the reactions you have learned so far, and thus predict the structure (correctly specifying regiochemistry and stereochemistry) of the major product(s) produced. 4. Be able to write detailed arrow-pushing mechanisms showing each step and the structure of all intermediates for (1) alcohol dehydration; (2) alcohol reaction with HX; (3) epoxide cyclization reactions; (4) epoxide ring-opening reaction under acidic and basic conditions; (5) various electrophilic addition reactions to alkenes and alkynes (HX, hydration, X ,2hydroboration); (6) various reactions involving cyclic oxonium and halonium ions; (7) reactions involving acetylide anions. Be clear with the intermediates involved. Based on the mechanisms, understand the regioselectivity and stereospecificity of those transformation. If carbocation is involved, consider the possibility of rearrangement to form more stable carbocation intermediate. 5. Based on y
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