E1 AND FRACTIONAL DISTILLATION 2011 SPRING

E1 AND FRACTIONAL DISTILLATION 2011 SPRING - E1:...

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Click to edit Master subtitle style 4/27/11 E1: Unimolecular Elimination Fractional Distillation Laboratory 7
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4/27/11 SN1 vs E1 (SN2 vs E2)
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4/27/11 SN1 vs E1
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4/27/11 E1 mechanism OH O H H H O H H H O H H Rate Determining Step Fast Fast Carbocation Intermediate OH H 3 PO 4 Heat
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4/27/11 SN1 and E1 pathways often compete OH O H H H O H H H O H H Rate Determining Step Fast Fast Fast Nucl Nucl - Carbocation Intermediate E1 Elimination SN1 Substitution
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4/27/11 Zaitsev’s rule More substituted bonds are more stable CH 2 H 3 C H 3 C Br CH 3 CH 2 H 3 C H 3 C CH 3 CH 2 H 3 C H 2 C CH 3 CH H 3 C H 3 C CH 3 -H + -H + Minor Major
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4/27/11 Procedure Ø Fractionally distill cyclohexene as it is formed Ø Dry product over K2CO3 Ø Purify cyclohexene via simple distillation Ø Dry again, if necessary Ø Test for unsaturation with Baeyer test
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4/27/11 Fractional distillation Clip hoses with metal clip Don’t use plastic connector on pot flask Insulate the pot flask, fractionation column and distillation head
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E1 AND FRACTIONAL DISTILLATION 2011 SPRING - E1:...

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