225Sp04 Test 5 - CHEMISTRY 225 TEST #5 JUNE 18, 2004 1. _...

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CHEMISTRY 225 T E S T # 5 1. ________ (25) JUNE 18, 2004 2. ________ (10) NAME _______________________________________________ 3. ________ (13) P I S T O N S R U L E ! 4. ________ (15) 5. ________ (12) TOTAL (75) 1. (25 Points) ORGANIC REACTIONS AND SYNTHESIS. a. ( ________ / 20) Demonstrate your understanding of alkyl halide reactions by completing FIVE of the following alkyl halide reactions with structures for the organic reactant, product, or reagent as required. If no reaction is expected under the reaction conditions, write " N.R ." and explain briefly why the reaction fails . If you complete all six equations be sure to indicate clearly which five you wish to have graded. Each reaction carries equal point value. Br CH 3 O 3 OH 2 2 I H 3 2 3 SH + N 3 BF 3
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2 NaH, PhCH 2 Br O OH O RO Organic Lett. 2004 , 6 , 1124 (-HBr) CH 3 + CH 3 ethanol + other products or Br NaCN b. ( ________ / 5) The S N 2 reaction is particularly useful for the formation of new carbon-carbon bonds at an sp 3 hybridized carbon. (3) Complete the equation below by identifying a pair of reactants that would combine to produce alkyne I by forming bond a in an S N 2 reaction. + CH 3 CCH 2 3 3 CCC H 2 CH 2 3 b a I (2) Explain briefly why the alternate approach involving formation of bond b would be less successful.
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3 2. (10 Points) MECHANISM I, TRANSITION STATES. a. ( ________ / 4) Sketch a picture of the transition state for the reaction below. CH 3 CH 2 CHCH 2 3 Br 3 2 O b. ( ________ / 6) Complete the following “miniessay” by circling the correct term of each pair. The first step in the S N 1 S N 2 reaction of 2-bromo-2-methylpropane is unimolecular dissociation to form a carbocation. This is a highly endothermic process so the transition state occurs early late
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225Sp04 Test 5 - CHEMISTRY 225 TEST #5 JUNE 18, 2004 1. _...

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