Chem210-1 F08 Ex1 p03a

Chem210-1 F08 Ex1 p03a - would they have different dipole...

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4. The compound piperidine is shown on the right: N H a) Reaction of piperidine with 1 equivalent of the compound n-butyllithium (a powerful base) leads to a proton transfer reaction which yields the conjugate base of piperidine. Provide a Lewis structure for the conjugate base of piperidine - you can use a "line structure" or condensed Lewis structures for simple C-C and C-H portions of the structure, but be sure to specify all charged atoms, heteroatoms, lone pairs and formal charges. (4 pts) b) Even though piperidine possesses a six-memebered ring like cyclohexane, piperidine exists in two distinct conformational forms which have different energies. Draw up below the two most likely structural forms for piperidine - make sure you include at least enough detail that a grader can distinguish between the two (you need NOT specify which is more stable) (6 pts) c) If each of your structures in (b) could be isolated as pure and stable molecular entities,
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Unformatted text preview: would they have different dipole moments? C i r c l e o n e- YES NO (2 pts) d) Could piperidine form hydrogen bonds to the following compounds? (C i r c l e each compound with which piperidine could H-bond): (4 pts) (CH 3 )NH 2 (CH 3 ) 2 NH (CH 3 ) 3 N (CH 3 ) 4 N e) Consider the conjugate acid of piperidine - the compound you'd get if you reacted piperidine with 1 equivalent of H-Cl. Circle each compound below to which the conjugate acid form of piperidine would H-bond: (4 pts) (CH 3 )NH 2 (CH 3 ) 2 NH (CH 3 ) 3 N (CH 3 ) 4 N f) If piperidine was reacted with acetic acid, would the resulting equilibrium give mostly the protonated form of the piperidine referred to in part (e) above, or would the equilibrium favor the reactants? (Circle the favored side of the equilibrium below) (4 pts) CH 3 CO 2 H + piperidine (products) N H 2 C H 2 C CH 2 N CH 2 H 2 C o r N H N H a n d...
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