Orgo Unit 6.3 Discussion

Orgo Unit 6.3 - negative charge on halogens make good leaving groups Additionally molecules with resonance stabilized negative charges also make

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Topic # 3: What structural and reactivity factors are necessary for E1 reactions to occur? According to our textbook, Organic Chemistry with Biological Applications, the requirements for E1 reactions are the same as for SN1 reactions. Moreover, the reaction proceeds in a similar fashion as well. The first step of the reaction entails the departure of a leaving group from a molecule, which results in a carbocation intermediate. The second step entails a base removing a proton from a molecule and the formation of an alkene. As in SN1 reactions, the first step of the E1 reaction is the departure of a leaving group. Thus, molecules with better leaving groups favor E1 reactions . As previously discussed, molecules with no negative charge (e.g., H2O, R-OH, NH3, R-NH2, or NR2H) make excellent leaving groups or molecules with stable negative charges (e.g.,
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Unformatted text preview: negative charge on halogens) make good leaving groups. Additionally, molecules with resonance stabilized negative charges also make good leaving groups. Additionally, we want a molecule that will form a stable carbocation once the leaving group departs. Accordingly, substrates that result in more highly substituted carbocations will favor E1 reactions. From what we already know about carbon atoms, they are electron donors, which will stable the carbocation. This is because alkyl groups donate electron density to stabilize the carbocation molecule. The last factor we consider is that we need a polar solvent for E1 reactions to occur . This will stabilize the carbocation intermediate. And as previously mentioned, the hydrogen that will be removed from the molecule should be beta to the leaving group for the alkene to properly form....
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This note was uploaded on 04/10/2011 for the course AAS 410.302.81 taught by Professor Thompson during the Spring '11 term at Johns Hopkins.

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