Chem 212
Survey of Organic and Biochemistry
Summer 2004
_____________________________
Print your full name legibly in the space above.
Exam 1: Ch. 1-4
24 June 2004
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:
a. HCO2- formic acid anion
b. CH3NH2 methylamine
c. C2H2 acetylene
2. State whether the structures in each pair below are identical, constitutional
isomers, or not related.
CH3
CH3
CH3
CH2 CH2 CHCH3
and
CH3 CH2 CH
CH3
Answer
and
Answer
Page 1
Chem 212
Survey of Organic and Biochemistry
Summer 2004
3. Tetracycline is one of the most commonly prescribed antibiotics in the United
States. Answer the following questions about the structure of tetracycline
21
20
N
HO
19
4
5
3
8
6
10
9
7
11
OH
OH
12
2
18
1
OH
16
17
22
14
15
O
OH
NH2
13
O
O
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
C1
C8
C3
C12
C6
N10
(the N attached to C-10)
e. Give approximations for the following bond angles:
C4-C5-C6
C13-C14-O14
C9-C10-C11
C16-C7-C8
f. Label the following atoms as primary (1°), secondary (2°), tertiary (3°), or
quaternary (4°):
C9
C19
C7
C8
Page 2
Chem 212
Survey of Organic and Biochemistry
Summer 2004
5. Using the following template, draw a Newman projection for 2,3-dimethylbutane
looking down the C2-C3 bond:
6. Give the IUPAC name for the following molecules
Name: _________________________________
Name: _________________________________
7. Below each name, draw the correct structure for these molecules.
3-cis, 5-trans-3,5-decadiene
trans-1-t-Butyl-2-methylcyclopentane (hint: “t-Butyl” = “tertiary butyl”)
8. The structure below represents glucose in a planar-hexagon drawing. Next to it, draw
a line angle structure using wedges and dashes to show the relationship between the
substituents on the ring.
OH
O H
H
H
OH
H
H
OH
HO
OH
Page 3
Chem 212
Survey of Organic and Biochemistry
Summer 2004
9. Draw a line angle structure for the following molecules:
a. C6H10O, with a ketone (may have other functional groups as well)
b. C6H10O, with an aldehyde (may have other functional groups as well)
c. C5H12O with an ether (may have other functional groups as well)
10. Draw the structure of the major organic products for each of the following reactions:
a. Cyclohexane + bromine treated with light
b. Cyclopentene + HCl
c. 1-pentene + H2O + H2SO4
d. trans-2-octene + H2 + catalyst
e. 2-methyl-2-pentene + bromine
11. Below is the structure of vitamin E. Based on this structure and what you know about
polarity, would you expect vitamin E to be soluble in oil or water? Explain your answer using
the concepts of polarity and functional groups.
OH
H 3C
CH3
H 3C
O
CH3
CH3
H 3C
CH3
CH3
Vitamin E (alpha-Tocopherol)
Page 4
Chem 212
Survey of Organic and Biochemistry
Summer 2004
13. What simple structural feature is responsible for the visible colors of licopene, beta carotene,
heme, chlorophyll, and bilirubin, along with many other organic compounds?
14. What is a carcinogen? Answer with a complete sentence.
15. Give one example of a medical use for capsaicin, which is the chemical that gives hot
peppers their flavor.
16. Briefly explain what is wrong with each of the following chemical names
a. trans-cyclopentene
b. cis-2-methyl-2-heptene
c. trans-1,1,-dimethylcyclopentane
Page 5