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International Chemistry Olympiad 2014 (Problems)

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Theoretical and Practical Problems of International Chemistry Olympiad 2014
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  46 th  International Chemistry Olympiad July 25, 2014 Hanoi, Vietnam THEORETICAL EXAMINATION WITH ANSWER SHEETS GRADING Country: Name as in passport: Student Code: Language:  The 46 th IChO – Theoretical Examination. Official English Version 2 GENERAL INTRODUCTION    You have additional 15 minutes  to read the whole set.    This booklet is composed of 9 problems. You have 5 hours to fulfill the problems.  Failure to stop after the STOP command may result in zero points for the current task.    Write down answers and calculations within the designated boxes. Give your work where required.    Use only the pen and calculator provided.    The draft papers are provided. If you need more draft paper, use the back side of the paper. Answers on the back side and the draft papers will NOT be marked.    There are 52 pages  in the booklet including the answer boxes, Cover Sheet and Periodic Table.    The official English version is available on demand for clarification only.     Need to go to the restroom – raise your hand. You will be guided there.    After the STOP signal  put your booklet in the envelope (do not seal), leave at your table. Do not leave the room without permission.  The 46 th IChO – Theoretical Examination. Official English Version 3 Physical Constants, Units, Formulas and Equations Avogadro's constant  N  A  = 6.0221 ×  10 23  mol  –1  Universal gas constant  R = 8.3145 J·K   –1 ·mol  –1  Speed of light c = 2.9979 ×  10 8  m·s  –1  Planck's constant h= 6.6261 ×  10  –34  J·s Standard pressure  p °  = 1 bar = 10 5  Pa Atmospheric pressure 1 atm = 1.01325 ×  10 5  Pa = 760 mmHg Zero of the Celsius scale 273.15 K Mass of electron m e  = 9.1094 ×  10  –31  kg   1 nanometer (nm) = 10  –9  m ; 1 angstrom (Å) = 10  –10  m 1 electron volt (eV) = 1.6022 ×  10  –19  J = 96485 J·mol  –1 Energy of a light quantum with wavelength λ    E   = hc  / λ  Energy of one mole of photons  E  m  = hcN  A  / λ  Gibbs energy G  =  H   – TS   Relation between equilibrium constant and standard Gibbs energy = exp G K  RT  ⎛ ⎞Δ⎜ ⎟−⎜ ⎟⎝ ⎠ o  van’t Hoff equation in integral form ⎟⎟ ⎠ ⎞⎜⎜⎝ ⎛ −Δ= 21012 11ln T T  R H  K  K   Relationship between internal energy, heat and work ∆ U   = q  + w   Molar heat capacity at constant volume vmv dT dU C   ⎟ ⎠ ⎞⎜⎝ ⎛ =   ,  Change in internal energy from T  1  to T  2  assuming constant C  v,m   U  ( T  2 )= U  ( T  1 )+ nC  v,m ( T  2  –  T  1 ), Spin only formula relating number of unpaired electrons to effective magnetic moment B.M.)2(  += nn eff  μ     The 46 th IChO – Theoretical Examination. Official English Version 4  Problem 1. Particles in a box: polyenes In quantum mechanics, the movement of π  electrons along a neutral chain of conjugated carbon atoms may be modeled using the ‘particle in a box’ method. The energy of the π  electrons is given by the following equation: 222 8 mLhn E  n  =  where n  is the quantum number ( n  = 1, 2, 3, …), h  is Planck’s constant, m  is the mass of electron, and  L  is the length of the box which may be approximated by  L  = ( k   + 2)×1.40 Å ( k   being the number of conjugated double bonds along the carbon chain in the molecule). A photon with the appropriate wavelength λ  may promote a π  electron from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). An approximate semi-empirical formula based on this model which relates the wavelength λ , to the number of double bonds k   and constant  B  is as follows: λ   (nm) =  B   )12( )2( 2 ++× k k   Equation 1 1. Using this semi-empirical formula with  B  = 65.01 nm  calculate  the value of the wavelength λ  (nm) for octatetraene (CH 2  = CH – CH = CH – CH = CH – CH = CH 2 ). 1. From the given semi-empirical formula, the wavelength λ  (nm) is calculated as follows: )12( )2(01.65)( 2 ++×= k k nm λ   For octatetraene molecule, with k = 4; = 260.0 nm  3 points Code:  Question 1 2 3 4 5 Total Examiner Mark 3 7 6 4 7 27 Theoretical Problem 1 5.0 %  of the total Grade

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