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Name: ____________________________
Chemistry 102, NSCC, Exam II
EXAM 2 (100 pts)
Tuesday, May 8th, 2007
1. (15 pts, 5 pts each) Name the following compounds
OH
O
Cl
O
H
OCH3
OH
Br
2. (15 pts, 5 pts each) Draw the structure of the following compounds
a. 2-methoxy-2,3-dimethylbutane (problem 13.16, part d)
b. 3-fluoro-2,4-pentanedione
c. 5-bromo-2-pentanethiol
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Name: ____________________________
Chemistry 102, NSCC, Exam II
3. (30 pts) Parts A to C of this problem refer to an alkane, a ketone, and an alcohol of similar mass,
each containing four carbons or less and the indicated molar mass.
a. (16 pts) Fill out the table below, ranking the compounds based on their boiling points [1
= highest, 3 = lowest]. Also indicate their solubility in water as either soluble or
insoluble
Compound
Alcohol
Molar Mass
(g/mole)
60
Alkane
58
Ketone
58
Boiling Point
Ranking
Solubility in Water
b. (8 pts) Based on the molar mass of each compound, what are their respective IUPAC
names? (use the back pages as scratch paper or the space below)
Compound
Alcohol
Molar Mass
(g/mole)
60
Alkane
58
Ketone
58
Name of the compound
c. (6 pts) Based on your boiling point ranking in part A, would you expect ketones to have
higher, lower, or similar boiling point then alcohols of comparable masses? Provide
Rationale for your answer.
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Name: ____________________________
Chemistry 102, NSCC, Exam II
4. (20 pts) (Problem 14.63c) Complete the missing steps in the reaction below and name the final
product
O
CH3
CH2
CH2
C
H
H+
H2
structure 2
(6 pts)
heat
Pt
structure 1 (6 pts)
light
Br2
Structure of final product (4 pts)
Name of final product ( 4 pts)
5. (20 pts) Using a combination of the reactions we have studies so far, indicate how you would
prepare the following, starting with the substances given and showing all the intermediate steps.
O
CH3
C
CH2 CH2
H
O
CH3 CH2 CH2 OH
CH3
C
CH3
O
CH3 C
CH
CH3
3
C
CH3
Name: ____________________________
Chemistry 102, NSCC, Exam II
EXTRA CREDIT
6. (4 pts) [Problem 13.63] A compound with formula C4H8O is synthesized from 2-methyl-1propanol and oxidized easily to give carboxylic acid. What is the structure of the compound?
7. (3 pts). Write the isomers of the carbonyl compounds of C3H6O (that is all the isomers you draw
must have a carbonyl group in them).
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