Chem 3AL - Lab Report #9

Chem 3AL - Lab Report #9 - Kylie 04 August 2010 Chem 3A Lab...

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Kylie 04 August 2010 Chem 3A Lab Experiment #10 Discussion: 1-bromopentane - in NaI/acetone: reacted and formed a yellow precipitate immediately, showing that the SN2 reaction of this substrate is favorable. 1-Bromopentane's straight chain structure makes it open to backside attack by NaI (no steric hindrance around the carbon attached to Br), and bromine is a good leaving group (relatively big and less electronegative, forming a weaker bond with C). - in Ethanoic AgNO3: the reaction took around 4 min. for a cloudy/white solution to appear, and additional heat (52'C) for over 4 min. resulted in a fully opaque solution. The SN1 reaction of this substrate isn't as favorable, and requires time and heat; it's more difficult for the bromine to leave on its own, since the alkane will be unstable with the positive charge (no stabilization by conjugation/resonance available). 1-chloropentane - in NaI/acetone: reacted and formed a white precipitate immediately, but heating for 30 sec. was required to keep the solution from returning to its clear state. It didn't completely react in room temperature (as predicted) because despite its straight chain structure, backside attack is difficult since chlorine isn't as good a leaving group as bromine is (it's smaller and more electronegative, more tightly bound to the carbon as a result). - in Ethanoic AgNO3: the solution remained clear, then became cloudy in 2 min. 2-bromopentane - in NaI/acetone: reacted and formed a white precipitate immediately, but heating for 20 sec.
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was required to keep the solution in its cloudy/white state (instead of becoming clear again). It didn't completely react in room temperature (as predicted), because the bromine isn't attached to an end carbon. As a result, NaI's backside attack on the second carbon is hindered by the methane attached to it.
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Chem 3AL - Lab Report #9 - Kylie 04 August 2010 Chem 3A Lab...

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