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HT2-03 - C hemistry 301-301A Hour Examination#2 There aint...

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Chemistry 301-301A - Hour Examination #2, November 17, 2003 There ain’t no answer. There ain’t going to be any answer. There never has been an answer. That’s the answer. Gertrude Stein 1 (20 points). Explain carefully why reaction (a) fails but (b) succeeds: O Na + Br H 2 O no reaction O H 2 O HBr OH Br + (a) (b) Explain carefully why reaction (c) fails but (d) succeeds: OH Na + OEt HOEt OH 2. Na + OEt O CH 3 S O 2 Cl (c) no reaction to give (d) 1. TsCl TsCl = O In part (c) there is a product formed - what is it?
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2( 20 points). (a) As you know, the E2 and S N 2 reactions often compete. For example, when cyclohexyl bromide is treated with sodium ethoxide in ethanol, both cyclohexyl ethyl ether and cyclohexene are formed. Please sketch very careful arrow formalisms for the formations of these compounds. 3D, please. Br Na + OEt HOEt OEt + (b) When 1 is the starting material, the product is overwhelmingly 2 . Little 3 is formed. Explain. Br (CH 3 ) 3 C Na + OEt HOEt OEt (CH 3 ) 3 C (CH 3 ) 3 C 2- cis 3 >> 1 (c) When 4
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