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Usnco Part 2

Usnco Part 2

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Not valid for use as an USNCO Olympiad National Exam after April 23, 2008.
 
Page 1
 
2008 U. S. NATIONALCHEMISTRY OLYMPIAD
 
NATIONAL EXAM—PART II
Prepared by the American Chemical Society Olympiad Examinations Task Force
OLYMPIAD EXAMINATIONS TASK FORCE
 
Arden P. Zipp, State University of New York, CortlandChair
 
Sherry Berman-Robinson,
Consolidated HS 
, Orland Park, IL (retired) Paul Groves,
South Pasadena HS 
, Pasadena, CAWilliam Bond,
Snohomish HS 
, Snohomish, WA David Hostage,
Taft School 
, Watertown, CTPeter Demmin,
 Amherst HS 
, Amherst, NY (retired) Adele Mouakad,
St. John’s School 
, San Juan, PRMarian Dewane,
Centennial HS,
Boise, ID Jane Nagurney,
Scranton Preparatory School,
Scranton, PAValerie Ferguson,
 Moore HS 
, Moore, OK Ronald Ragsdale,
University of Utah
, Salt Lake City, UTKimberly Gardner,
US Air Force Academy
, Colorado Springs, CO
 
DIRECTIONS TO THE EXAMINER–PART IIPart II
of this test requires that student answers be written in a response booklet of blank pages. Only this “Blue Book” is graded fora score on
Part II
. Testing materials, scratch paper, and the “Blue Book” should be made available to the student only during theexamination period. All testing materials including scratch paper should be turned in and kept secure until April 23, 2008, afterwhich tests can be returned to students and their teachers for further study.Allow time for the student to read the directions, ask questions, and fill in the requested information on the “Blue Book”. When thestudent has completed
Part II
, or after
one hour and forty-five minutes
has elapsed, the student must turn in the “Blue Book”,
Part II
of the testing materials, and all scratch paper. Be sure that the student has supplied all of the information requested on thefront of the “Blue Book,” and that the same identification number used for
Part I
has been used again for
Part II
.There are three parts to the National Olympiad Examination. You have the option of administering the three parts in any order, andyou are free to schedule rest-breaks between parts.
Part I 60 questions single-answer multiple-choice 1 hour, 30 minutesPart II 8 questions problem-solving, explanations 1 hour, 45 minutesPart III 2 lab problems laboratory practical 1 hour, 30 minutes
A periodic table and other useful information are provided on the back page for student reference. Students should be permitted touse non-programmable calculators.
 DIRECTIONS TO THE EXAMINEE–PART IIDO NOT TURN THE PAGE UNTIL DIRECTED TO DO SO. Part II
requires complete responses to questions involvingproblem-solving and explanations.
One hour and forty-five minutes
are allowed to complete this part. Be sure to
print
your name,the name of your school, and your identification number in the spaces provided on the “Blue Book” cover. (Be sure to use the
same
 identification number that was coded onto your Scantron® sheet for
Part I
.) Answer all of the questions in order, and use both sidesof the paper. Do not remove the staple. Use separate sheets for scratch paper and do
not
attach your scratch paper to thisexamination. When you complete
Part II
(or at the end of one hour and forty-five minutes), you must turn in all testing materials,scratch paper, and your “Blue Book.” Do not forget to turn in your U.S. citizenship statement before leaving the testing site today.
 
Key for 2008 National Olympiad (part 2)
Page 2
 
Not valid for use as an USNCO Olympiad National Exam after April 23, 2008.
 
1.
(14%) Benzene, C
6
H
6
, reacts with Br
2
in the presence of FeBr
3
as a catalyst to give an organic compound with the percentagecomposition by mass; C 30.55%, H 1.71%, Br 67.74% and hydrogen bromide.
a.
 
Determine the empirical formula of the compound.
b.
 
When 0.115 g of this compound are dissolved in 4.36 g of naphthalene the solution freezes at 79.51 ˚C. Pure naphthalenefreezes at 80.29 ˚C and has a
= 6.94 ˚C·
m
 –1
. Determine the molar mass and molecular formula of the compound.
c.
 
Write a balanced equation for the reaction.
d.
 
Calculate the theoretical yield for the organic compound when 4.33 g of of benzene is reacted with an excess of bromine.
e.
 
If the actual yield of the reaction is 5.67 g, what is the percentage yield?
 
f.
 
i.
Write structures for the possible isomers that could be formed in this reaction.
ii.
Identify the major isomer(s) formed in this reaction and explain your reasoning.
 
a)
 
convert masses to moles:
1.71 g H
"
1 mol1.008 g
#
 
$
 
%
 
&
 
'
 
(
 
= 1.70 mol (
÷
0.848) = 2.00
 
30.55 g C
"
1 mol12.011 g
#
 
$
 
%
 
&
 
'
 
(
 
= 2.54 mol (
÷
0.848) = 3.00
 
67.74 g Br
"
1 mol79.90 g
#
 
$
 
%
 
&
 
'
 
(
 
= 0.848 mol (
÷
0.848) = 1.0
 These numbers are whole numbers, so the empirical formula must be C
3
H
2
Brb)
 
Δ
T = 80.29 – 79.51 = 0.78
o
C. Plugging this value into the formula for freezing point depression gives,
"
T =
m
and
m
= 0.78
o
C6.94
o
C/
m
=
0.11
m
 
0.11molkg 
"
0.00436 kg= 0.00048 mol so, MM=0.115 g0.00048 mol= 240 g
#
mol
-1
 240 / 117.9 = 2.03 which is approximately 2, so the molecular formula must be C
6
H
4
Br
2
 c)
 
C
6
H
6
+ 2Br
2
 
r
C
6
H
4
Br
2
+ 2 HBrd)
 
The theoretical yield is:
4.33 g C
6
H
6
 
"
1 mol C
6
H
6
78.11 g C
6
H
6
#
 
$
 
%
 
&
 
'
 
(
 
"
1 mol C
6
H
4
Br
2
1 mol C
6
H
6
#
 
$
 
%
 
&
 
'
 
(
 
"
235.89 g C
6
H
4
Br
2
1 mol C
6
H
4
Br
2
#
 
$
 
%
 
&
 
'
 
(
 
= 13.1 g C
6
H
4
Br
2
 e)
 
Percent yield is:
5.67 g13.07 g
"
 
#
 
$
 
%
 
&
 
'
 
(
100% = 43.4%
 The possible isomers for i. are, ii. the major products are,
BrBrBrBrBrBr
 
BrBrBrBr
 because –Br is an ortho-para director. The para isomershould be the most prominent product because of sterichindrance for the ortho product.
 
 
Not valid for use as an USNCO Olympiad National Exam after April 23, 2008.
 
Page 3
 
2.
(10%) Photochemical smog is formed through a sequence of reactions, the first three of which are given below. Smog is formedwhen the O(g) produced in reaction (3) reacts with organic molecules.(1) N
2
(g) + O
2
(g)
r
2NO(g)(2) 2NO(g) + O
2
(g)
r
2NO
2
(g)(3) NO
2
(g) + h
ν
 
r
NO(g) + O(g)
a.
 
For reaction (1),
∆ 
 H 
º = +180.6 kJ·mol
 –1
. Calculate the bonddissociation energy of NO(g).
b.
 
Calculate the entropy change for the first reaction.
c.
 
Determine the minimum temperature at which reaction (1) becomesspontaneous.
d.
 
For reaction (3),
∆ 
 H 
º = +306 kJ·mol
 –1
. If the energy for thisreaction were provided by sunlight, estimate the wavelengthrequired and specify the region of the spectrum containing thiswavelength.a)
 
The overall enthalpy change can be estimated from the bond dissociation energies via the equation,
"
H = Energy of bonds broken
#
$
Energy of bonds formed
#
 
180.6 kJ = 941 kJ + 498 kJ
"
2
#
BDE
NO
 
s
o, BDE
NO
=629 kJ
"
mol
 –1
 b)
 
Similarly,
"
S
o
= 2S
o
(NO)
#
S
o
(N
2
) + S
o
(O
2
)
( )
 
"
S
o
= 2(210.6)
#
(191.5) + (205)
( )
= 24.7 J
$
mol
-1
$
K
-1
 c)
 
Utilize the equation,
"
G
o
=
"
H
o
 
#
T
"
S
o
 
, and set
Δ
G
o
to zero to find the minimum temperature.
0 = 180.6 kJ
"
mol
-1
 
#
T
$
0.0247 kJ
"
mol
-1
"
K
-1
( )
, so T = 180.6 kJ
"
mol
-1
0.0247 kJ
"
mol
-1
"
K
-1
= 7311 K
 d)
 
First convert to energy per molecule,
3.06
"
10
3
 Jmol
"
1 mol6.022
"
10
23
molecules
#
 
$
 
%
 
&
 
'
 
(
 =
5.08
"
10
-19
 Jmolecule
. Now calculate wavelength of light with this energy,
=h
#
cE
=
6.626
$
10
-34
J
#
s
( )
3.0
$
10
8
m
#
s
-1
( )
5.08
$
10
-19
J
#
molecule
%
 
&
 
'
 
'
 
(
 
)
 
*
 
*
 =
3.91
$
10
-7
m
(per molecule) = 391 nm (in the ultraviolet).
3.
 
(12%) Aniline, C
6
H
5
NH
2
, reacts with water according to the equation: C
6
H
5
NH
2
(aq) + H
2
O(l)
s
C
6
H
5
NH
3+
(aq) + OH
 –
(aq)
 
In a 0.180 M aqueous aniline solution the [OH
 –
] = 8.80
×
10
 –6
.
a.
 
Write the equilibrium constant expression for this reaction.
b.
 
Determine the value of the base ionization constant,
b
, for C
6
H
5
NH
2
(aq).
c.
 
Calculate the percent ionization of C
6
H
5
NH
2
in this solution.
 d.
 
Determine the value of the equilibrium constant for the neutralization reaction;
 
C
6
H
5
NH
2
(aq) + H
3
O
+
(aq)
s
C
6
H
5
NH
3+
(aq) + H
2
O(l)
 e.
 
i.
Find the [C
6
H
5
NH
3+
(aq)] / [C
6
H
5
NH
2
(aq)] required to produce a pH of 7.75.
ii.
Calculate the volume of 0.050M HCl that must be added to 250.0 mL of 0.180 M C
6
H
5
NH
2
(aq) to achieve this ratio.
 a)
b
=
 C
6
H
5
NH
3+
[ ]
OH
-
[ ]
C
6
H
5
NH
2
[ ]
 
Bond Dissociation Energy, kJ
mol
 –1
 
N–N 193N=N 418N
N 941O–O 142O=O 498
S
o
, J
mol
 –1
K
 –1
 
N
2
(g) 191.5O
2
(g) 205.0NO(g) 210.6NO
2
(g) 240.5O(g) 161.0

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