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