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Rxn Cards Test-3 10-28-07

Rxn Cards Test-3 10-28-07 - Chapter 7-10 Reaction Cards for...

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Chapter 7-10 Reaction Cards for Test #3 Smith, 2nd Ed. Chemistry 624
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Product and Mechanism tBuOH Me OK Et CH 3 - I Br NaOH, AgNO 3 Br NaI, Acetone I EtSK, DMF Cl NaN 3 , DMF OH H + , EtOH NaI, Acetone Br LG Nuc, solvent ??? ??? ??? ??? ??? ??? ??? ??? S N 2 and S N 1 tBuOH Me OK Et CH 3 - I Br NaOH, AgNO 3 OH Br NaI, Acetone I I EtSK, DMF SEt Cl NaN 3 , DMF N 3 OH H + , EtOH OEt NaI, Acetone Br I S N 1 yielding a racemic product S N 1 yielding a racemic product S N 2 w/ inversion S N 2 w/ inversion LG not connected to Stereocenter LG Nuc, solvent Nuc S N 2 w/ inversion S N 2 w/ inversion Me O CH 3 Et Stereocenter Not involved in S N 2 Product and Mechanism Ph H Et Et Br Ph Excess NaOEt Br or Br NaOEt t BuOK ??? ??? ??? E1 and E2 Ph H Et Et Br Ph Excess NaOEt Br or Br NaOEt t BuOK or or Ph Ph Et Et Ph Ph Et Et Ph Ph Et Et these are all the same most substituted Bulky base goes after most accessible ! -proton
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Product and Mechanism Cl CH 3 D H NaH ? ? E2 Elimination in Cycloalkanes with NaH Small Base (sterically speaking) Cl CH 3 D H NaH CH 3 D H more substituted Cl D H H H CH 3 H(-)
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