orgo ch7

alcohols

weak acids and bases, react with active metals to form metal alkoxide, not good leaving group must be converted to weak base for sn1 and sn2

alcohol reaction with hydrohalic acid

react with hcl, hbr, and hi, secondary and tertiary allylic and benzylic follow sn1, methyl and primary alcohol follow sn2

alcohol with alkylsulfonates as leaving group

alcohol converted to alkyl sulfonate by treating with ester like tscl, mscl, tfcl, oms, otf

alcohol using halogenating agents

pbr3 and socl3 react with primary and unhindered secondary alcohol

Mitsunobu reaction

primary and secondary alcohols react with pph3, dead, hx, if chiral carbon change configuration

Preparation of ethers

intramolecular reaction produce cyclic ether

reaction of ether with hbr, hi, trimethylsilyl iodies

sn2 reactions

ethers

can be cleaved on reaction with trisilyl iodide

reaction of epoxides

reactive towards nucleophiles due to ring strain, the ring opens

thiols and thioethers

cannot undergo substitution reaction, used as nucleophile in sn1

thiols

form thiolate anion using hydroxide ion or tertiary amine as bases, thiolate bases good nucleophiles for sn2 of alkyl halide, alkyl sulfonate