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1º Alcohols (2 eq.) + H2SO4 (cat.), heat
symmetric, linear ether is produced with water
1º Alcohol + NaH, R—Br
Asymmetric, linear ether is produced
1º Alcohols + Bulky alkene
asymmetric bulky ethers is produced
Acid-Catalyzed Ether Cleavage
Ether + HX, heat
Separates ether and adds halogen where the oxygen was (two products)
Alcohol + TIPS—Cl, Et3N
Replaces -OH with -OTIPS
R—OTIPS + TBAF, H3O+
Replaces -OTIPS with -OH and also produces F-TIPS