Organic Chemistry I
CHEM
First
2423
2423
EXAM
Do not open or begin this exam until instructed. The exam has a total of 100 points and includes
10 questions. Only legible answers written on the exam will be considered for grading. All
pertinent information needed for the exam is given. Notes and textbooks are not permitted. Use
your time wisely.
Total Points: 100/Time: 1 Hr and 30 Min
Last Name:
First Name:
Class Section:
Your Score
DIRECTIONS- Please answer all questions in the space provided as completely and clearly as
possible. Show all your work for the writing portions of the exam. A periodic table is attached
at the end of this exam.
1. A. Draw structures of the following organic molecules:
a. 1-ethyl-3-methylcyclohexane
b. 5-ethyl-4-propyldecane
B. Give the correct IUPAC name for the following structures:
(d) _____________________________________
(e) _____________________________________
2. Identify the functional groups in the following compound and name each functional group.
3. Add the possible formal charges on the atoms in the following molecule?
3. Draw two possible resonances for each of the following compounds:
:O:
..
CH3 - C - CH = CH - CH - CH3
4. Write valence Lewis (electron dot) structures for each formula below. Show all
bonding electrons as dashes and all non-bonding electrons as dots.
a) CO32-
b) HCN
c) NH4 +
d) HNO3
e) CH2Cl2
5. Identify the nucleophile (Nu-) and electrophile (E+) in each reaction below and label
them. Then, add curved arrows to the reactions to indicate the flow of electrons.
6. Label the acid, conjugate acid, base, and conjugate base in each reaction below .
a)
CH3OH
b)
CH3OCH3
+
CH3O- Na+
NaH
+
BH3
H3C
+
O
CH3
c)
BF3 + CH3NH2 →
BH3
+
H2
7. Draw and name the cycloalkanes with the formula C6H12. You can use line drawings
or condensed drawings. Do not give me carbon skeletons or expanded drawings as final
answers.
8. Convert the following chair conformations into planar cyclohexane skeletal structures.
Be sure to use wedges and dashes to show the stereochemistry of the different
substituents off of the ring.
9. The diaxial conformation of cis-1,3-dimethylcyclohexane is approximately 23 kJ/mol less stable
than the diequatorial conformation. Draw the two possible chair conformations and explain why
there is a large energy difference between the two.
10. Draw all conformational isomers in Newman projection formulae for propane and draw comparative
energy diagram for each of them.
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