Frechet09Finalsol - Chemistry 3A May 2009 Page 2 of 14 1. (...

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Chemistry 3A May 2009 Page 2 of 14 1. ( 10 Points) (a) Write a balanced equation showing starting materials, other necessary inputs, and products in the “Syngas” process. (b) Write a balanced equation illustrating the Fischer-Tropsch process (c) An acid has pK a = 3.25 What is its K eq ? Show the equations used to calculate K eq . Answer: K eq = ______________ (d) Write a balanced equation for the combustion of 1-propyne in oxygen (e) How many σ (sigma) and how many π (pi) bonds are there in the molecule shown below O CCC H 2 CN Answers: # of Sigma bonds = ___________ # of Pi bonds = _____________
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Chemistry 3A May 2009 Page 3 of 14 2. (11 Points) (a) The energy difference between substituted two cyclohexane conformers A and B is +1.2 Kcal mole -1 calculate the equilibrium constant K eq at 300 K. Show the equation used for your calculation. (b) A sample of 2-bromobutane has [ α ] D = +8°; given that pure (S)-2-bromobutane has [ α ] D = +24° what is the % ee of the sample? What is the percentage of (S)-2-bromobutane in the sample? Show your calculation (c). Show the structures of the molozonide and ozonide intermediates obtained in the reaction of ozone with 2,3-dimethyl-2-butene. Molozonide Ozonide (d) Name the famous scientist who proposed the concept and established the scale of electronegativity. Answer: _________________________________ (e) Name the famous scientist who discovered enantiomers. Answer: ___________________________________ Answer: K eq = Answer. % ee = % of (S)-2-bromobutane in sample = ozone
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Chemistry 3A May 2009 Page 4 of 14 3. (12 Points) (a) Write a step by step mechanism for the reaction below: (b) propose a synthesis of: Show all steps and reagents. No mechanisms are needed. (hint: think “allylic”) CH 3 CH 2 CH 2 OH SOCl 2 N CH 3 CH 2 CH 2 Cl CH 2 OH from and H 2 CC H 2
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Chem 3A May 2009 Page 5 of 14 4. (38 points) Multiple choice questions. This question continues on several pages. Clearly darken the letter code of the correct answer (e.g. change (e) into ). Each question has only one correct answer, which is worth 3 points, The E2 reaction is a 1,2-elimination of a proton, H + , and a leaving group, Y - . In an E2 reaction, how many σ (sigma) bonds are there between the proton and the leaving group? (a) 1 (b) 2 (c) 3 (d) 4 (e) 5 (f) 6 (g) 8 Lindlar’s catalyst is made of: (a) Mg in ether (b) Pd /Charcoal (c) Pd/CaCO 3 /quinoline (d) Pd(OAc) 2 /Charcoal (e) PdCl 2 /Ni/C What is the major elimination product for the reaction of 2-bromo-3-methylhexane with hydroxide ion?
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This note was uploaded on 06/26/2010 for the course CHEM 3A taught by Professor Fretchet during the Fall '08 term at University of California, Berkeley.

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Frechet09Finalsol - Chemistry 3A May 2009 Page 2 of 14 1. (...

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