PS_7 - O O heat O O Cl CCl 3 O Cl CCl 3 + Initiation Steps...

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1 Problem Set #7 Swager 5.12 (Due Friday, November 4, 2011 at 4PM) 1. Consider the following reaction that occurs by a free radical chain mechanism. A 2 + CD ----> AD + AC The bond dissociation energies (kcal/mol) are: A-A 40 A-C 70 A-D 65 C-D 80 a. Write the initiation and propagation steps for this reaction. b. Calculate the reaction’s free energy. c. Which is the rate limiting step? Explain.
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2 2. Give the dominate mono-bromination product(s) from these radical reactions. Explain your answers. 1eq NBS RO-OR, heat 1 eq NBS RO-OR, heat 1 eq NBS RO-OR, heat 3. Rank order the reactivity of the indicated hydrogens for an abstraction reaction by a free radical halogenation. Explain your reasoning. H 2 C CH 2 CH 3 C H 2
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3 4. Radical chlorination reactions with CCl 4 and peroxides begin with the two initiation steps shown below. Which of the compounds A-D is the product when the hydrocarbon shown reacts with CCl 4 in the presence of peroxides? Provide a curved arrow mechanism.
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Unformatted text preview: O O heat O O Cl CCl 3 O Cl CCl 3 + Initiation Steps heat (CH 3 ) 3 CO-OC(CH 3 ) 3 CCl 3 Cl 3 C Cl Cl CCl 3 CCl 3 Cl Cl 3 C Cl A B C D 2 4 5. Which reaction will proceed at the highest rate? Explain your answer and why the other reactions have lower relative rates. Cl I Br I CN CN CN CN NaCN DMF NaCN H 2 O NaCN CH 3 OH NaCN DMSO A B C D 5 6. Rank the following series of compounds on their ability as nucleophiles (1=best, 4=worst). 7. Rank the following compounds as leaving groups (1=best, 4=worst). H 2 O NH 3 PH 3 PH 2 Series 1 Series 2 OEt OCH(CH 3 ) 2 OCH(CF 3 )CH 3 O 2 CCF 3 NH 2 OH S O O CH 3 O S O O CF 3 O 6 8. Rank order (1 = fastest ) the relative rates of the following compounds for S N 2 reaction with NaCN in dimethylsulfoxide (DMSO) solvent. Would you expect larger or smaller relative rate differences for S N 2 reaction with NaOCH 3 ? (Hint- consider the relative sterics of each Nu--)...
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PS_7 - O O heat O O Cl CCl 3 O Cl CCl 3 + Initiation Steps...

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