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    The Story of Ethyl & Grignard

    Ethyl and Grignard met at the H bar - a popular spot for continuous operators to hang out.  Ethyl noticed Grignard as soon as he transported himself in.  At first their attraction was only Van der Waals, but after Grignard bought Ethyl some ethanol the conversation became quite friendly.
     

    The couple fell deeper into the potential well of love.  Grignard felt his rigid rotor gain a quanta and he knew it was time to operate on Ethyl. 

    "Would you commute with me, Ethyl?  My Mercedes Benzyl is parked right outside."   Ethyl was excited about the opportunity to hybridize with the best molecule in the bar and left without hesitation.
     
    The reaction proceeded at a fast rate, and Grignard was quick to distill the small talk down to the synthesis that was at hand. He exposed his nucleophile and asked Ethyl to remove her protecting group. Ethyl was taken aback by this lowering of the energy barrier. 

    "Shouldn't we take precautions against side reactions?"  Grignard laughed - he knew the conditions were right and no unwanted products would be formed.
     
    Ethyl removed her protecting group and exposed her lone pairs.  Grignard, who to this point was in a ground state, realized the potential and entered an excited state. The transition shocked Ethyl, who moaned,

     

    "I've never seen such a long alkyl group before." Grignard smiled with pride, but in his mind he worried whether or not his long chain would cause steric hindrances.


    Ethyl and Grignard maneuvered near each other without any hydrophobic tendencies. Ethyl's feelings were basic: She wanted maximum overlap. Grignard backside attacked ethyl, taking advantage of her fully exposed carbo-cation.  "Ooh," Ethyl said, "no solvent molecule has ever done that to me before.  All they ever did was deprotinate me - I was left all alone feeling rather negative."
     
    Grignard added himself to her, but he never equilibrated and was forced to reverse his reaction.
     
    "Don't tease me with your carbo-anion ... Complete the mechanism."  When Grignard backside attacked for the second time, he could feel the hyper-conjugation taking place.  Grignard maneuvered her lone pairs and pushed his electrons deep into her conjugated pi system.  Ethyl shrieked at the thought of this un-natural anti-bonding configuration, but Grignard explained that what they were doing was symmetry allowed.  Afterall, this was a hetero-lytic reaction.
     

    Now that the initialization step was complete, the long series of propagation steps started. Ethyl started feeling rather radical, and her new reactivity caused Grignard to vibrate faster.  Grignard could begin to feel a coupling between his vibration and rotation.  Obviously he was dealing with no simple basis set, for she was currently fully orthogonal.  Grignard whispered to Ethyl, "You better watch out because I'm going to normalize you."  Ethyl reminded Grignard that she can't be diagonalized like any other molecule, and her wavefunction was too complicated for even the most sophisticated algorithm to elucidate.
     

    They were both happy until Grignard asked Ethyl if she'd mind if he had her spectra taken.  The thought of being probed by an electromagnetic field horrified her.  If that wasn't all, the spectra would likely be published in one of those chemistry magazines ... and her pi system and lone pairs would be exposed for all to see.
     
    Ethyl entered a new resonance structure, shifted a negative charge to her carboxyl group, and made further conjugation by Grignard unfavorable. To make matters worse, Grignard forgot Ethyl's IUPAC name! Ethyl put her protecting group back on and kicked Grignard out of her beaker.
     
    As Grignard walked back to his Benzyl he realized that he was a little dehydrated.  The night was still young, so he convected himself back to the H Bar, where he continued to operate frictionlessly on other hermitian functions.

     

                               - Eric Daymo -