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Unformatted text preview: CHEMISTRY 2261
EXAM 1 September 16, 2009 LIST
number NAME (PRINT)____________________________________________
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 TOTAL 1. (10 pts) Fill in the missing elements in their proper positions in the Periodic Table: 2. (7 pts) Add formal charges to the following Lewis structures where necessary. 3. (10 pts) Draw acceptable Lewis structures of the following neutral compounds by adding all the
nonbonding electrons, multiple bonds and any necessary formal charges. 4. (4 pts) Calculate the equilibrium constant (Keq) for the following acid-base reaction. 5. (6 pts) Fill in boxes on the right (using s, p, sp, sp2, or sp3) to indicate relative energies of the 5 indicated
orbitals. Note that there are seven boxes and only five orbitals, so two of the boxes will be left empty. least
Increasing Energy p sp sp2 50 25 sp3
stable 0 (8 pts) For the molecule shown below, identify the hybridization (sp, sp2, or sp3) for each of the labeled
a C d e N OH + O – O g h N b H O f a b c d e f g h 7. (4 pts) Rank the following group of compounds in order of decreasing acidity. 2 8. (6 pts) For the following group of anions:
• provide the hybridization of the indicated carbon atom
• rank in order of increasing base strength. hybridization
hybridization H H H H hybridization CC CC
H H 1
(ethyl anion) HCC H 2
(ethynyl anion) < weakest
base H 3
(ethenyl anion) < strongest
base increasing base strength
9. (8 pts, 4 pts ea) For each acid-base reaction:
! Indicate whether Keq is greater than or less than 1 (>1 or <1)
! Indicate the effect responsible for the difference in acidity (electronegativity, size, inductive,
resonance, or hybridization) which influences the equilibrium constant.
a) N N + Keq b) NH N + H Effect O O O
OH Keq H
H + F O O
O Effect 3 + F OH 10. (6 pts, 2 pts ea)
a) Determine the pH at which 99% of CH3CH2SH (pKa = 7.9) will be in a form that possesses a charge. pH =
b) Determine the pH at which 9% of CH3CH2SH (pKa = 7.9) will be in a form that possesses a charge. pH =
11. (4 pts) Rank the following compounds in order of increasing boiling point.
1H 2 N OH O 3 4 lowest boiling highest boiling 12. (5 pts) Give the product of the following reaction (as a properly drawn Lewis structure): 13. (4 pts) Draw a Lewis structure for each molecule below. Indicate (circle) which molecules (if any) will
have a molecular dipole. (Hint: consider the hybridization of the central atom). BH3 CH3+ 4 H3O+ 14. (8 pts) Draw structures corresponding to the following IUPAC names: 15. (4 pts, 2 pts ea) Answer the following questions about the pair of Newman projections drawn below
representing two staggered conformations of an alkane.
a) Identify (circle) the lowest energy conformation. b) Provide a skeletal structure and IUPAC name for the alkane represented by this pair of Newman
projections. 16. (6 pts) Add the six remaining C-H bonds to the chair cyclohexane drawing provided below.
H 5 ...
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