CHE 2201, Section 101
Fall 2013
Exam 1C
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Page 1: _____/ 21 points
Page 2: _____/ 17 points
Page 3: _____/ 16 points
Page 4: _____/ 28 points
Page 5: _____/ 18 points
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0
1. Answer the following questions for the structure below:
a.) (2 points) Fill in all lone pairs on the structure.
b.) (4 points) Use the electronegativity values to classify the specified bonds as nonpolar covalent, polar covalent, or ionic.
O-C
O-K
2. (5 points) Convert the following line-bond structure to a skeletal structure.
3. (5 points) Draw a line bond structure for the following molecules from its condensed
structure:
4. (5 pts) Draw the structure of 4-tert-butyl-2,2-dimethyloctane.
1
pts /18 pts
5. (8 pts) There are several problems with the following structure:
Circle the statements that correctly identify what should be changed. Circle all that apply.
a. You cannot have π bonds in a ring.
b. The carbon indicated by
does not obey the octet rule.
c. The carbon-carbon-carbon bond angle indicated by
should be 109.5°.
d. Oxygen should have a formal charge of -1.
6. (9 pts) Label the relationship between each pair of structures as
A.
B.
C.
D.
pts /17 pts
Same molecule
Resonance structures
Constitutional isomers
None of the above
2
7. (4 pts) Circle all the acids that would react with hydroxide to form the products.
8. (4 pts) Circle which functional group is not present in the following molecule?
A. amine
B. arene
C. ester
D. ether
9. (4 pts) Circle which of the following statements is not true?
A. Molecular orbital theory uses bonding and antibonding orbitals.
B. The antibonding orbital is higher in energy than the bonding orbital.
C. The antibonding orbital is made by subtracting one atomic orbital from another atomic orbital.
D. The best bonding situation is when the bonding and antibonding orbitals are both filled.
10. (4 pts) Which of the following molecules has a molecular dipole moment of zero?
3
pts /16 pts
11. (5 pts) Draw one isomer of an amide with the molecular formula C4H9NO.
12. (11 pts) a. Draw the resonance structures for the molecule below.
b.) Draw the resonance hybrid.
c.) Circle the resonance structure that contributes the most to the resonance hybrid.
13. (12 pts) Each structure has 3 atoms in bold. Give the hybridization of the central atom, its
geometry, and the bond angle defined by the three nuclei in bold.
4
pts /28 pts
14. (4 pts) Calculate the formal charge of the atoms in bold. Any lone pairs in these structures
have been explicitly drawn.
15. (6 pts) Identify the Lewis acid and the Lewis base in the following reaction. Draw a curved
arrow to show how the electrons move in the reaction.
16. (8 pts) Circle the more acidic molecule and the correct explanation for what makes it more
acidic. The donated proton is indicated in bold.
5
pts /18 pts