Molecular Design


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Chemistry presentation on Ethers

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Molecular Design

  1. 1. By: Harkaran, Dhruvin, Tegbir, Harman
  2. 2. <ul><li>A functional group, where an “oxygen atom is attached to two alkyl groups” (Methyl, Ethyl etc...) </li></ul>O R R “ Where R represents an alkyl group”
  3. 3. Methyl Ethyl Propyl Isopropyl CH 3 CH 2 CH 3 CH 2 CH 2 CH 3 CH 3 CH CH 3 Butyl Sec-Butyl Iso-Butyl Tert-Butyl CH 2 CH 2 CH 2 CH 3 CH 3 CH CH 2 CH 3 CH 3 CH 2 CH CH 3 CH 3 C CH 3 CH 3
  4. 4. CH 3 – O – CH 2 – CH 2 – CH 3 methyl propyl <ul><li>IUPAC Name: 1-methoxypropane </li></ul><ul><li>Common Name: methyl propyl ether </li></ul>H 3 C —O— CH CH 3 CH 3 methyl isopropyl <ul><li>IUPAC Name:2-methoxypropane </li></ul><ul><li>Comman Name: isopropyl methyl ether </li></ul>
  5. 5. <ul><li>1)Find the Largest alkyl group attached to the oxygen atom </li></ul><ul><li>use this as the parent alkane </li></ul><ul><li>Give it an alkane name (“suffix”) </li></ul><ul><li>2)Treat the second alkyl group as an alkoxy group </li></ul><ul><li>Replace the –yl in the alkyl name with –oxy, to represent that it is attached to the oxygen.(“prefix”) </li></ul><ul><li>3)Give the alkoxy group a position number according to the position number of carbon atom attached to the oxygen on alkyl group with longest chain. </li></ul><ul><li>4)Put the prefix and suffix together. </li></ul>
  6. 6. <ul><li>1)CH 3 – O – CH 2 – CH 2 – CH 3 </li></ul><ul><ul><li>Larger chain alkyl group: propyl </li></ul></ul><ul><ul><li>3 carbon atoms, therefore root: prop </li></ul></ul><ul><ul><li>Alkane, -ane ending </li></ul></ul><ul><ul><li>Propane, suffix </li></ul></ul>2)CH 3 – O – CH 2 – CH 2 – CH 3 <ul><ul><li>Methyl </li></ul></ul><ul><ul><li>Methoxy, prefix </li></ul></ul>3)Position Number of Methoxy? <ul><ul><li>CH 3 – O – CH 2 – CH 2 – CH 3 </li></ul></ul><ul><li>4)Put the prefix and suffix together </li></ul><ul><ul><li>1-methoxypropane </li></ul></ul>1 2 3 1 <ul><ul><li>1-methoxy </li></ul></ul>
  7. 7. H 3 C —O— CH CH 3 CH 3 <ul><li>Longest chain: isopropyl </li></ul><ul><ul><li>3 carbons, pro </li></ul></ul><ul><ul><li>One bond, Alkane ending, -ane </li></ul></ul><ul><ul><li>Propane </li></ul></ul><ul><li>Second Group: Methyl </li></ul><ul><ul><li>Change to alkoxy group, methoxy </li></ul></ul>3) Position Number: 2-methoxy 2 1 3 2 4) Put the prefix and suffix together: 2-methoxypropane
  8. 8. <ul><li>Place the alkyl groups joined by the oxygen atom as the prefix alphabetical </li></ul><ul><li>CH 3 – O – CH 2 – CH 2 – CH 3 </li></ul>propyl methyl <ul><li>“ methyl propyl” </li></ul><ul><li>2) Put ether at the end of name as the suffix </li></ul><ul><ul><li>methyl propyl ether </li></ul></ul>
  9. 9. H 3 C —O— CH CH 3 CH 3 1)Isopropyl methyl 2)Isopropyl methyl ether
  10. 10. <ul><li>There is bent shape around the oxygen atom ,which is formed due to a </li></ul><ul><li>C-O bond, meaning that the oxygen molecule has 2 lone pairs which ends up giving it a slight “–” charge and the two Carbons on either side, a slight “+” charge </li></ul>I llustration : The two lone pairs are responsible for making the molecule polar. <ul><li>cannot use hydrogen bonds because lacks O-H, the H-F or the N-H bonds. </li></ul><ul><li>does not use hydrogen bonding, unless if the bond is provided by a water molecule as now it has the O-H required to use the Hydrogen bond </li></ul><ul><li>because of small polarity, it is soluble in water as it uses hydrogen bonds </li></ul><ul><li>being a polar molecule, it will use dipole- dipole interactions which are relatively weak </li></ul><ul><ul><li>reason why, boiling and melting points of ethers are much lower when compared to those of other polar compounds like alcohol </li></ul></ul>
  11. 11. <ul><li>Ethers are extremely flammable and explosive and are recommended to be used with caution. Should be kept away from sources of ignition </li></ul><ul><li>While stored, an Ether may form explosive peroxides </li></ul><ul><li>Vapors may cause drowsiness and repeated exposure may cause dry and irritated skin. </li></ul><ul><li>An Example of a compound containing this functional group is Methoxyflurane which is commonly known as Penthrane. It is a halogenated ether. </li></ul>
  12. 12. <ul><li>used for general anesthetics until side effects such as nausea and vomiting were discovered </li></ul><ul><ul><li>Ex) ethoxyethane “diethyl ether” </li></ul></ul><ul><ul><ul><li>clear, colourless, and highly inflammable liquid </li></ul></ul></ul><ul><ul><ul><li>solubility in water is very limited </li></ul></ul></ul><ul><ul><ul><li>to used as a recreational drug 19th centaury </li></ul></ul></ul><ul><ul><li>Ex) methoxyflurane </li></ul></ul><ul><ul><ul><li>powerful pain relieving agent which is used as an emergency painkiller in some hospitals </li></ul></ul></ul><ul><ul><ul><li>receive decreasing concentrations due to the risk of nephrotoxicity (damage to the kidney) </li></ul></ul></ul>Ethoxyethane Molecular formula C 2 H 5 OC 2 H 5 Molar mass 74.12 g/mol Melting point − 116 °C Boiling point 34.6 °C Methoxyflurane Molecular formula C 3 H 4 Cl 2 F 2 O   Molar mass 164.965 g/mol Melting point − 35 °C Boiling point 105 °C
  13. 13. <ul><li>Polyethylene glycol (PEG) </li></ul><ul><ul><li>Type of polyether (Polyethers are compounds with more than one ether group) </li></ul></ul><ul><ul><li>Properties </li></ul></ul><ul><ul><ul><li>Molecular formula C2n+2H4n+6On+2 Molar mass 44n+62 Flash point 182 - 287 °C (The temperature at which any flammable material will burst into flame) </li></ul></ul></ul><ul><ul><ul><li>PEG is soluble in water because of the presence of the OH group </li></ul></ul></ul><ul><ul><li>Clinical Uses: </li></ul></ul><ul><ul><ul><li>Used in laxatives (drugs or foods that induce bowel movements, loosen stools and used for treatment against constipation) </li></ul></ul></ul><ul><ul><ul><li>Used as lubricant for colonoscopy and bowel surgery </li></ul></ul></ul><ul><ul><li>Other Uses: </li></ul></ul><ul><ul><ul><li>Used in a number of toothpastes to prevent chemical compounds from adhering in the toothpastes </li></ul></ul></ul><ul><ul><ul><li>injection of PEG leads to faster recovery of spinal injuries in research animals. </li></ul></ul></ul><ul><ul><ul><li>used in eye lubricant drops </li></ul></ul></ul>Polyethylene glycol (PEG)
  14. 14. <ul><li>Diethyl ether </li></ul><ul><ul><li>Properties </li></ul></ul><ul><ul><li>Molecular formula C 4 H 10 OC 2 H 5 OC 2 H 5 Molar mass 74.12 g/mol, Appearance clear, colorless liquid Boiling point 34.6 °C (307.75 K) </li></ul></ul><ul><ul><li>Uses: </li></ul></ul><ul><ul><ul><li>used as a general anesthetic </li></ul></ul></ul><ul><ul><ul><li>inhibits alcohol dehydrogenase ,slows down the metabolism of ethanol a type of alcohol found in beer and rum. </li></ul></ul></ul><ul><ul><ul><li>Used in the production of cocaine </li></ul></ul></ul>