Summary of Alcohol Syntheses, Ch. 10 (and Review of Old Ones). Potassium (K) analogous. 1 Key way to convert alcohol to alkoxide, reactive as SN2 nucleophile and E2 base. Alkoxide formation-SN2 route to ether 2 The electrophile R'-X must be SN2 reactive, preferably 1º with a good leaving group Mech? 3 -Li is analogous for making RLi, which also act analogously. -MgBr is spectator: R is key. 1 carbon Mech 4 extension Mech 5 All three Mech 6 R groups can be different. At least 2 Mech 7 R groups must be the same 2-Carbon Mech 8 chain extension 9 Mech 10 Mech 11 NaBH4 will Mech not react with esters Review Routes to Alcohols 10 11
Summary of Alcohol Syntheses, Ch. 10 (and Review of Old Ones). 1 Potassium (K) analogous. Key way to convert alcohol to alkoxide, reactive as SN2 nucleophile and E2 base. 2 Alkoxide formation-SN2 route to ether The electrophile R'-X must be SN2 reactive, preferably 1º with a good leaving group Mech? 3 -Li is analogous for making RLi, which also act analogously. -MgBr is spectator: R is key. 4 1 carbon extension Mech 5 Mech 6 All three R groups can be different. Mech 7 At least 2 R groups must be the same Mech 8 2-Carbon chain extension Mech 9 Mech 10 Mech 11 NaBH4 will not react with esters Mech Review Routes to Alcohols 10 11
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