ORGANIC CHEMISTRY Chapter 6 6.15 Organic Synthesis Functional Group Transformations Using SN2 Reactions Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 6 6.15 Organic Synthesis: Functional Group Transformations Using SN2 Reactions
ORGANIC CHEMISTRY Chapter 6 o SN2 reactions are highly useful in organic synthesis because they enable use to convert one functional group into another functional group transformation(functional group interconversion) Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 6 SN2 reactions are highly useful in organic synthesis because they enable use to convert one functional group into another —— functional group transformation (functional group interconversion)
ORGANIC CHEMISTRY Chapter 6 RI Alkyl iodide NaoH roH Alcohol Natch ROCH ether Nao-C-CH3 RX Ro-C-CH ester or 20 NaoNO, R=Me.1° ChroNO Methyl nitrate XCI. Br NaCN or I ron Nitrile a RN3 alkyl azide Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 6 NaO C O CH3 RO C O RX CH3 NaI NaOH NaOCH3 NaONO2 NaCN NaN3 RI ROH ROCH3 CH3ONO2 RCN RN3 Alkyl iodide Alcohol Ether Ester Methyl nitrate Nitrile Alkyl azide R= Me, 1° or 2° X= Cl, Br or I
ORGANIC CHEMISTRY Chapter 6 Nash RSH Thiol NascN rscn Alkyl thiocyanate NaCH(CO2CH3)2 RCH(CO2CH3)2 Dimethyl alky malonate R-X NaC≡C-C3,RC=C- CH Alkyne NH RNH Br Alkylammonium bromide N(CH3)3 R(CH33NBr P(CH3)3 Alkyltrimethylammonium bromide R(CH3)3 PBr Alkyltrimethylphosphonium bromide Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 6 NaC C RC C CH3 CH3 X NaSH NaSCN NaCH(CO2CH3)2 RSH RSCN RCH(CO2CH3)2 RNH3Br R(CH3)3NBr NH3 N(CH3)3 P(CH3)3 R(CH3)3PBr Thiol Alkyl thiocyanate Dimethyl alkylmalonate Alkyne Alkylammonium bromide Alkyltrimethylammonium bromide Alkyltrimethylphosphonium bromide R
ORGANIC CHEMISTRY Chapter 6 AgNO R-X R-ONO2 +AgX EtoH CHCl Room Tempt. heat CHo-CHCHoCl AgCl↓ instantly CH3)3CCI (CH3)2CHCI AgNO3 AgCl 2 or 3 minium EtOH CH3 CH2 CH2CI AgCI CHO-CHC cl Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 6 R X R ONO2 + AgX AgNO3 EtOH CH2Cl CH2 CHCH2Cl CH2 CHCl Cl AgCl instantly AgCl 2 or 3 miniums Room Tempt. heat (CH3)3CCl (CH3)2CHCl CH3CH2CH2Cl AgNO3 EtOH AgCl