Ethers Nomenclature Chem 2325
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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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