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Page 1: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

4/30/2008 1Dr. Abdullah SAleh

Page 2: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

4/30/2008 2Dr. Abdullah SAleh

Page 3: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

4/30/2008 3Dr. Abdullah SAleh

Page 4: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

E2 Mechanism

4/30/2008 4Dr. Abdullah SAleh

Page 5: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

• The E2 Reaction

• E2 reaction involves concerted removal of the proton, formation of the double bond, and

departure of the leaving group

• Both alkyl halide and base concentrations affect.

Dr. Abdullah SAleh 54/30/2008

Page 6: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

E1 Mechanism

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Page 7: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

• The E1 Reaction• The E1 reaction competes with the SN1 reaction and likewise

goes through a carbocation intermediate

Dr. Abdullah SAleh 74/30/2008

Page 8: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

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Page 13: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

Potassium tert-butoxide is an extremely bulky

base and is routinely used to favor E2 reaction

4/30/2008 Dr. Abdullah SAleh 13

Page 14: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

• If the base is small, SN2 competes strongly

because approach at carbon is unhindered

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Page 18: 4/30/2008 Dr. Abdullah SAleh 1 - Hashemite University · PDF filePotassium tert-butoxide is an extremely bulky base and is routinely used to favor E2 reaction 4/30/2008 Dr. Abdullah

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END OF CHAPTER 6

Dr. Abdullah I. Saleh

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