Ethers - Organic Chemistry I - Lecture Slides, Slides of Organic Chemistry

Download Ethers - Organic Chemistry I - Lecture Slides and more Slides Organic Chemistry in PDF only on Docsity! Ethers R-O-R or R-O-R´ Nomenclature: simple ethers are named: “alkyl alkyl ether” “dialkyl ether” if symmetric CH3 CH3 CH3CH2-O-CH2CH3 CH3CH-O-CHCH3 diethyl ether diisopropyl ether docsity.com CH3-O-C(CH3)3 tert-butyl methyl ether (MTBE) If complex, the ether part is named as an “alkoxy” group: CH3-O- = methoxy CH3CH2-O- = ethoxy, etc. CH3-O-CH2CH2CH2-O-CH3 1,3-dimethoxypropane HO-CH2CH2-O-CH2CH3 2-ethoxyethanol docsity.com Synthesis of ethers 1. Williamson Synthesis. R-O-Na+ + R´-X  R-O-R´ + NaX R´-X should be CH3 or 1 o SN2 mechanism docsity.com Mechanism for the Williamson Synthesis = SN2 R´-X should be CH3 or 1 o R O + R' X RDS R O R' + X docsity.com R-OH + Na  R-O-Na+  R-O-R´ R´-OH + HX  R´-X (CH3)2CH-OH + Na  (CH3)2CH-O -Na+ +  CH3CH2CH2-O-CH(CH3)2 CH3CH2CH2-OH + HBr  CH3CH2CH2-Br isopropyl n-propyl ether note: the alkyl halide is primary!  docsity.com Acids Bases Metals Oxid. Reduc. Halogens NR NR   NR   some NR NR   NR NR NR  NR NR  NR NR NR NR NR NR R-H R-X R-OH R-O-R docsity.com Reactions, ethers: 1. Acid cleavage. R-O-R´ + (conc) HX, heat  R-X + R´-X CH3CH2-O-CH2CH3 + HBr, heat  2 CH3CH2-Br docsity.com Mechanism 1) O CH2CH3CH3CH2 + HX H O CH2CH3CH3CH2 + X H O CH2CH3CH3CH22) X + CH3CH2 X + HO CH2CH3 3) CH3CH2 OH + HX CH3CH2 OH2 4) CH3CH2 OH2 + X CH3CH2 X + H2O + X SN2 SN2 docsity.com Alcohols: nomenclature syntheses later reactions 1. HX 2. PX3 3. 4. as acids 5. ester formation 6. oxidation docsity.com Ethers nomenclature syntheses 1. Williamson Synthesis 2. reactions 1. acid cleavage docsity.com Mechanisms: Free radical substitution SN2 SN1 Memorize (all steps, curved arrow formalism, RDS) and know which reactions go by these mechanisms! docsity.com