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Ethers Nomenclature

by: Faiqa Rahman

Ethers Nomenclature Chem 2325

Faiqa Rahman
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About this Document

Introduction to Ethers and how to name them.
Organic Chemistry
Dr. Christina Thompson
Class Notes
Organic Chemistry, Ethers, nomenclature, Epoxides




Popular in Organic Chemistry

Popular in Chemistry

This 6 page Class Notes was uploaded by Faiqa Rahman on Friday February 5, 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 67 views. For similar materials see Organic Chemistry in Chemistry at University of Texas at Dallas.


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Date Created: 02/05/16
Chapter  14  –Ethers-­‐Nomenclature     Remember!!     Polar  and  aprotic!                  R  and  R’  are  alkyl  or  aryl     O                Example:  diethyl  ether     CH CH 3­‐O-­‐2H CH   2 3     R    R’       3 • Oxygen  is  sp  hybridized   • Tetrahedral  angle  is  110   ο • C-­‐O  bonds  are  polar   Physical  Properties:   • They  have  a  lower  boiling  point  than  alcohol  because  they  can’t   hydrogen  bond  to  ethers.     • However  they  can  hydrogen  bond  to  H O  and  alcohols   2 As  a  solvent:   • They  are  unreactive  to  strong  bases     • Dissolve  nonpolar  and  polar  substances   Grignard’s:  complexation  of  ethers  with  Grignard  reaction  stabilizes   reagent   Crown  Ethers-­‐  complex  metal  cations  in  center  of  ring.   The  size  of  the  ether  ring  will  determine  which  cation  is  can  solvate   better   Example:         Nomenclature:   Name  the  two-­‐alkyl  groups  attached  to  Oxygen  and  add  ether.   Be  sure  to  name  them  alphabetically!   For  Example:                   Diethyl  ether     O     IUPAC:          CH     3                3   2methoxy-­‐2-­‐methylpropane      H C3­‐O-­‐C-­‐CH 3     2     1    CH 3            O     methoxy  cyclohexane           Practice!!     4       3   2   O   2-­‐ethoxy-­‐3-­‐methylbutane                   2-­‐ethoxy-­‐3-­‐methylbutane       1                               O       diphenyl  ether             O                   methoxy  benzene               or                      methyl  phenyl  ether                   2-­‐ethoxy    ol          2-­‐ethoxy  ethanol     2        OH       **Alcohol  has  a  higher  priority     O     1   than  ether**   Cyclic  Ethers:   Heterocyclic:  Oxygen  is  part  of  the  ring          O   Epoxides:     Also  known  as  Oxiranes       Oxetanes:          O         Furans:       Oxolanes:         O   O     Note:  Furans  are  saturated  whereas  Oxolanes  are  not.     Pyrans:     Oxanes:         O     O     Note:  Pyrans  are  saturated  whereas  Oxanes  are  not.     O   Dioxanes:           O           Epoxide  Nomenclature:   Name  starting  alkene  and  add  oxide         O     cyclohexene  oxide           1   O     2   3                                  trans  1,2  epoxy-­‐4  methyl  cyclohexane      4         CH 3            O                                  cis  2,3-­‐epoxy  4  methoxy  hexane               OCH 3       How  can  you  tell  if  it’s  cis  or  trans?   Look  at  the  epoxy!!   Example:         O                                                     Same  side  =  cis                              O                                                           Opposite  sides  =  trans                 3  membered  oxirane  is  the  parent.  Therefore  Oxygen  is  1  and   the  Carbons  are  2  &  3.  Substituents  are  named  alphabetically.     1            O       trans  2,3  dimethyl  oxirane   2   3         O                    2,2  diethyl  3  isopropyl  oxirane                    O                                               5  chloro  1,3  dioxane     O    Cl       Note:  Since  the  ring  is  symmetric,  it  doesn’t  matter   which  oxygen  is  1.  You  name  substituents  first,  then   oxygen,  then  the  ring.  


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