CHM 250 Exam II
6/15/2015 Summer 2015 Last name:____________ First name:________________
Left-side Neighbor:
Right-side Neighbor:
I. Multiple choices/Blank-fill-ins (3 pts per entry, 42 pts)
1. The most reactive alcohol (when reacting with a hydrogen halide) with the molecular
formula of C4H10O is __________. (a name or a structure)
2. _____________has the highest boiling point. (choose one of the following four
compounds).
CH3CH2CH2OH
CH3CH2F
CH3CH2OH CH3CH2CH3
3. Write the structure of a tertiary alcohol ___________.
4. The most stable carbocation with the molecular formula of C4H9+ is: ___________.
5. Write the structure of a secondary alkyl halide _____________.
6. The name of the mechanism by which methanol reacts with hydrogen bromide forming
methyl bromide and water is ______________.
7. The IUPAC name of the following compound is __________________. 8. The nucleophile in the following substitution reaction is _____________. 1 CHM 250 Exam II
6/15/2015 Summer 2015 9. Please label (a) a transition state
(b) an intermediate (c) the product on the
potential energy diagram shown below for a multi-step reaction. (total 9 pts) 10. According to Hammond’s Postulate, the transition state in the rate-limiting step of the
following reaction
has a structure most closely resembles to the structure of __________________ (must be
one of intermediates or reactants or products).
11. ________________ is the most reactive hydrogen halide when reacting with an
alcohol producing an alkyl halide and water. (fill in a name or a structure) 12. Show your understanding to the mechanism of the following reaction by giving the
key cationic intermediate ____________
I2 I NaHCO3
HO O O O 2 CHM 250 Exam II
6/15/2015 Summer 2015 II. Please give the structure of principle organic product of each reaction, please specify
stereochemistry if it applies (38 pts): 1. + HBr (1 molar equivalent) HO OH NaOCH2CH3/ethanol
heat 2. Br Br 3. H3C NaOEt/EtOH 4. 5. 6. + Br2 H2O 7. 8.
3 CHM 250 Exam II
6/15/2015 Summer 2015 . 1). BH3 THF 9. 2). H2O2, OH- 10. 11. III. Please give the detailed mechanism of following reaction by showing all
elementary steps, using curved arrows to show the flow of electrons. If any lone
pairs are involved in a reaction, they must be shown. (12 pts) 4 CHM 250 Exam II
6/15/2015 Summer 2015 HO I
+ HI + H2O IV. Consider the reaction:
(1) Please give the detailed mechanism of this reaction, using curved arrows to
show the flow of electrons. If any lone pairs are involved in a reaction, they
must be shown. (9 points)
(2) What is the name of the mechanism? (3 points)
(3) What is the rate-limiting step? (3 points) 1 2 3 4 5 6 7 8 9 5 10 11 12 13 14 CHM 250
meth eth Exam II
6/15/2015
prop but pent hex hept oct non 6 dec Summer 2015
undec dodec tridec tetradec

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