Chem 212
Survey of Organic and Biochemistry
Spring 2005
_____________________________
Print your full name legibly in the space above.
Exam 1: Ch. 1-5
1 March 2005
Instructions:
1. If you leave the room for any reason you may not return to continue the exam.
2. No books or notes of any kind are permitted. You may borrow a model kit.
3. Put all your answers on this exam paper. If you want something graded which is
written on scratch paper, you must indicate so in the regular space for the answer.
Good Luck!
1. Draw a reasonable Lewis structure for each of the following, showing all lone
pairs and formal charges where relevant:
a. CO32- carbonate anion
b. CH3CH2+ ethyl cation
c. HONO
2. State whether the structures in each pair below are identical, constitutional
isomers, cis-trans isomers, or not related.
H3C
CH 3CH(CH 3)CH 2CH 2CH 2CH(CH 3)CH 2CH 2CH 3
H3C
CH3
CH3
CH3
H3C
CH3
CH3
CH3
CH3
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Chem 212
Survey of Organic and Biochemistry
Spring 2005
3. Answer the following questions about the structure below.
H3C
CH3
5
4
1
7
6
3
2
10
CH3
8
9
HO
a. How many hydrogen atoms are in the structure? ___________
b. On the structure above, indicate with an arrow one bond which can freely rotate
around 360°.
c. Circle and name one functional group in the molecule.
d. Use the VSEPR method to predict the geometry around each of the following
atoms (linear, triangular planar, tetrahedral, triangular bipyramidal, octahedral)
C1
C6
C2
C7
C3
C10
e. Give approximations for the following bond angles:
H-O-C
C4-C5-C6
C10-C6-C7
C1-C2-C3
f. Label the following atoms as primary (1°), secondary (2°), tertiary (3°), or
quaternary (4°):
C3
C9
C4
C10
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Chem 212
Survey of Organic and Biochemistry
Spring 2005
5. Using the following template, draw a Newman projection for 1,1-dichloro-2methylbutane looking down the C1-C2 bond:
6. Give the chemical name for the following molecules:
CH3
H3C
CH3
H3C
H3C
Br
CH3
H3C
CH3
OH
7. Next to each name, draw the correct structure for these molecules.
1,4-Butanediol
2-Methyl-2-propyl-1,3-propanediol
3,3-Dimethylcyclohexanethiol
p-Methyl anisole
o-Chloro toluene
2-Bromo-1-ethyl-4-nitrobenzene
trans-2-Methyl-3-hexene
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Chem 212
Survey of Organic and Biochemistry
Spring 2005
9. Draw a line angle structure for the following molecules:
a. C5H8, with an alkene (may have other functional groups as well)
b. C8H14O2, with an ester (may have other functional groups as well)
c. C7H16O with a tertiary alcohol (may have other functional groups as well)
10. Draw the structure of the starting materials and the organic products for each of the following
reactions:
a. 1-Methylcyclohexene treated with bromine
b. Ethylcyclohexane treated with bromine and light
c. 1,4-Dichlorobenzene treated with fuming sulfuric acid (H2SO4)
d. Benzene treated with bromine and FeBr3
e. 1-Pentene treated with HCl
f. 1-Octene treated with water and sulfuric acid (H2SO4)
g. 2-Propanol treated with chromic acid (K2Cr2O7)
h. 4-Methyl phenol treated with sodium hydroxide (NaOH)
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Chem 212
Survey of Organic and Biochemistry
Spring 2005
11. Explain why the boiling point of 1,2-ethanediol (198 ºC) is so much higher than that of 1propanol (97 ºC) even though their molecular weights are about the same.
12. Both 2,6-Diisopropylcyclohexanol and an intravenous anesthetic Propofol are insoluble in
water. Show how these two compounds can be distinguished by their reaction with aqueous
sodium hydroxide.
CH3
H3C
OH
CH3
CH3
CH3
OH
CH3
CH3
H3C
Propofol
13. Show how to prepare 2-Methyl-2-propanol from 2-methyl-1-propanol.
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