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Ethers- Williamson Ether Synthesis

by: Faiqa Rahman

Ethers- Williamson Ether Synthesis Chem 2325

Marketplace > University of Texas at Dallas > Chemistry > Chem 2325 > Ethers Williamson Ether Synthesis
Faiqa Rahman

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About this Document

How to do Williamson Ether Synthesis as well as alternatives when dealing with phenols.
Organic Chemistry
Dr. Christina Thompson
Class Notes
Organic Chemistry, Ethers, Williamson Ether Synthesis
25 ?




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This 8 page Class Notes was uploaded by Faiqa Rahman on Monday February 8, 2016. The Class Notes belongs to Chem 2325 at University of Texas at Dallas taught by Dr. Christina Thompson in Spring 2016. Since its upload, it has received 31 views. For similar materials see Organic Chemistry in Chemistry at University of Texas at Dallas.


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Date Created: 02/08/16
Chapter  14  –Ethers-­‐  Williamson  Ether  Synthesis     • Involves  an  SN  attack  of  alkoxide 2on  unhindered  primary  halide   or  tosylate   • Alkoxide  is  commonly  made  by  add  Na,  K  or  NAH  to  the  alcohol         −               −   R   O     R’ X   R O R’  X                                   Phenyl  Ethers:     • Phenoxide  ions  are  easily  produced  because  the  alcohol  proton  is   acidic   • Phenyl  halides  and  tosylates  cannot  be  used  in  this  synthesis   method.        OH     O −                 Base                         Why  can’t  you  do  a  Williamson  Ether?     Remember  you  can’t  backside  attack  a  ring!     Because  Williamson  does  SN backside  attack,  you  can’t  have  2    ring  as   a  leaving  group.  So  when  you  have  an  ether  like  this:         O                 Then  you  must  use  this  as  a  leaving  group      O −   X     Or                     If  using  phenoxide,  then  it  must  be  the  one  to  do  the  attack     Alkoxymercuration/Demurcuration:   **Alcohol   Use  Mercuric  acetate  with  Alcohol     attaches  to  the   more     Hg  (OAc)   2 substituted                          R-­‐OH  Carbon**   ROH            Hg       O-­‐R     O-­‐R     NaBH 4     Hg   H   Cleavage  by  HI/HBr:         Step  1:  Protonation  of  Oxygen:       Step  2:  Halide  attacks  carbon  and  displaces  alcohol       Step  3:  Alcohol  further  reacts  with  acid  to  make  another  mole  of  alkyl   halides.               R  groups  become  alkyl  halides.    Remember!!:  It  doesn’t  work  with  phenols!!       H     You  can’t   O  +   backside  attack   rings!!!   Br −   However….            O          OH     HBr   Br                 +             Examples:           −     NaH   −   OH   O     Br                            O      O −                                                                               I   KOMe    O                OAc          OAc   Hg(OAc) 2        Hg     OH                   Hg(OAc) 2   O            O   NaBH 4               Try  this!       ?   ?   O                 First  you  have  to  determine  which  of  these  would  be  the  best   nucleophile  and  electrophile.          X   OH     +               OR        HO      X   **Leaving  group                  +   is  not  on  phenol**         Answer:        X   HO      O   NaOH                                +         Next  Problem:                             Cl                   HBr       ?   O       Answer:     Cl   Cl                                 HBr      O   +   Br        O      H         Cl     Cl   Cl       HBr   +        O      O      H           2   Br         Cl         Br         Last  Problem:     ?         OH          O   Answer:           H SO   2 4     OH             Hg(OAc) 2   MeOH     NaBH 4        OCH 3         Autoxidation:     • Ether  slowly  oxidizes  to  hydroperoxides  and  diakyl   peroxides.     • Both  are  highly  explosive!!  


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