Friday_Session_1_sol

Friday_Session_1_sol - O A H OH OH Has 6 electrons cand be...

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Chem 3580 Spring 2009 Friday Session - Week #1- Solutions Examples of some antiaromatic compounds and H NMR observations H H H Br H ! 16.4 ! 8.0 H ! 6.0
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1. Which ones would be antiaromatic and which ones would be aromatic if planar? N B CH 3 .. 2— (a) (b) (c) (d) 2— = Aromatic: (b) (d) Antiaromatic: (a) (c) 2. Compound A loses its proton more slowly than compound B . Explain. Use chemical structures to clarify your reasons. H CN A Ph Ph CN Ph Ph 4 ! electron system; antiaromatic; higly unstable; hence, its formation will be slow, i. e., H + loss will be very slow - H + H CN B Ph Ph CN Ph Ph No unusuall instability of this conjugate base; - H + 3. In a reaction with acid, cycloheptatrienone is protonated on the carbonyl oxygen to give a stable cationic product. Explain the stability of the protonated product. Use chemical structures to support your reasoning.
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Unformatted text preview: O A + H + OH OH Has 6 ! electrons; cand be planar and aromatic. Stable because it is aromatic 4. We will do these next week after we have covered more reactions 5. O CH 3 H O CH 3 H AlCl 3 H CH 3 H H CH 3 + AlCl 3 S N 2 attack on epoxide; inversvion at that carbon Inversion of configuration (R-isomer) (R-isomer). R-designation remained unchanged because priorities of groups changed (phenyl group replaced Oxygen) O Cl 3 Al O H AlCl 3 ———————————————————————————————————————————— 6. Cl Cl + Cl Cl AlCl 3 Cl H Cl—AlCl 3 Cl + + HCl AlCl 3 AlCl 3 H Cl—AlCl 3 + + AlCl 4 AlCl 3 HCl 7. We will do this question next week...
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Friday_Session_1_sol - O A H OH OH Has 6 electrons cand be...

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