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Microsoft word - chem233-spring2014-ex1-practice.doc
Chem 233: Organic Chemistry I
Dr. Marc Anderson
Exam 1 // Spring 2014 // practice
 your exam must be in pencil
 ear plugs
are encouraged, but headphones are
 a non-graphing calculator and organic model kits
are allowed allowed
 Cell phone calculators are always forbidden
 calculators / models may not be shared
(10 pts) Please draw the major resonance structures of compounds
Your final Score: / 100 total
. Your answers must show arrows indicating electron
movement to give rise to the resonance structures. Minor
resonance structures showing charge separation should be omitted.
(10 pts) What is the formal charge of each indicated atom shown below
(20 pts) Please identify the following for the molecules drawn to the right. a
. The hybridization at the observed positions in the molecules below. (2 pts each)
. The names of the indicated functional groups in the drawings above. (2 pt each)
(8 pts) Please answer the questions below about the compounds
propanol (propyl alcohol, H3C-CH2-CH2-OH, pKa = 16
) or acetic acid (H3C-CO2H, pKa = 5
. Which is the stronger acid? (1 pt)
Why? Please provide two or three short sentences that concisely explains the chemical reason for the selected
acid being stronger. Please include a simple figure that supports your chemical reasoning. (4 pts)
For acetic acid only, please draw the full balanced equilibrium equation that occurs in the presence of water.
When drawing the acid and its conjugate base, please draw in Kekulé line format, explicitly showing all atoms. Please also draw arrows that represent the reaction mechanism that occurs during this reaction (hint: the mechanism is very simple and consists of two arrows) (3 pts)
(8 pts) Please supply an IUPAC names for the following compounds. You can use either systematic or common naming
(8 pts) Please draw a structure in skeletal / zig-zag format for the compound:
(10 pts) Note the energy diagram below showing the rotation of the CH2-CH2 bond in the molecule 1-iodopropane (I-
-CH3) when answering question parts a
below. When drawing Newman projections, assume we’re looking down
the boldfaced bond (see above) and the iodide group is closest to us, while the CH3 is farther from us.
“Torsional angle” between the iodide and CH3 groups
. Please draw a Newman projection corresponding to the anti conformation
(1800 in the drawing above) of
Please draw a Newman projection corresponding to a lower-energy eclipsed conformation
of this molecule (2400 in
the drawing above). There are two possible conformations, just draw one of them.
Please draw a Newman projection corresponding to a gauche conformation
of this molecule (3000 in the drawing
above). There are two possible conformations, just draw one of them.
In one word, what is the source of strain that causes the gauche conformation to be slightly higher in energy than
10 : 20 : 30
draw the unique mono-halogenation products. Label the products a
b) calculate the % of each product, using the selectivity data provided
c) After calculating the %, please re-write the %
under each molecule
Circle the major product
*** for full credit, make sure you’ve follow
these instructions !!! (it simplifies grading) ***
(12 pts) The monobromination reaction shown here proceeds through a four step free radical chain reaction
mechanism to generate a single major product in high yield. The overall reaction is analogous to radical chlorination.
Please draw a valid “electron pushing” mechanism for the reaction indicated. Hint, the reaction consists of four steps,
and uses fishhook arrows. For the last step (termination), there are many possibilities, please just supply two
reasonable termination events
Scratch paper: Feel free to use, but this must be turned in with your exam.
Abbreviated periodic table ….
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