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chm2210ps7sol - Organic Chemistry I Problem Set 7 Solutions...

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Organic Chemistry I Problem Set 7 Solutions Free Radical Reactions I. Answer the following questions. 1. What is the hybridization of a free radical? sp 2 2. In what type of orbital is the unshared, unpaired electron held? Unhybridized p orbital 3. What is the geometry of a free radical atom? Trigonal planar II. Complete the following reactions. List all major products. If no reaction occurs write N.R. 1. No reaction - No free radical conditions listed!! CH 4 + Cl 2 (excess) Cl Cl + + polychloro products Cl 2 , light 2. Br Br 2 (1 mol) 300° 3. Cl 2 ROOR Show all products (limit) Cl Cl Cl Cl + + + 4. 5. Br Br 2 (limit) 300° Br 6. Br 2 (limit) heat 7. Br Br Br 2 light
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III. Cyclobutane reacts with bromine to give bromocyclobutane, but bicyclo[1.1.0]butane reacts with with bromine to give 1,3-dibromobutane. Account for the differences between these reactions. Br 2 heat Br Br Br Br 2 heat Br Br Br Br Br Br + Br After initiation where the bromine free radical is generated from Br 2 by the heat, the normal reaction would be propagation step 1 in which the C-H bond is broken producing
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