Organic reactions 1

Created by jclqrs 

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alcohol --> ether (using primary/unhindered alkyl halide)

Williamson ether synthesis [SN2]

thiol --> sulfide (using sulfonate ester)

williamson ether synthesis [SN2] - w/ sulfur

alkene --> ether (alcohol solvent)

alkoxymercuration-reduction

primary alcohol --> symmetrical ether

alcohol dehydration, harsh conditions [SN2]

tertiary alcohol --> unsymmetrical ether (primary alcohol solvent)

alcohol dehydration, mild conditions; make sure solvent does not form carbocation too [SN1]

alkene --> unsymmetrical ether

alkene addition that produces the same carbocation intermediate as alcohol dehydration

alkene --> epoxide (syn addition)

peroxycarboxylic acid (mCPBA, MMPP) [similar to bromonium ion]

halohydrin (O, X are anti) --> epoxide

cyclization of halohydrin ("intramolecular williamson ether") [intra- SN2]

epoxide --> glycol (inversion)

acid-catalyzed epoxide ring opening

epoxid --> glycol (syn)

oxidation with OsO4 [similar to ozonolysis]

alkene synthesis

E2

two-carbon chain extension

add HBr to alcohol; create Grignard reagant; attack epoxide

alkylating agents

sulfonate esters, alkyl halides

primary alcohol --> carboxylic acid

oxidation with KMnO4 (second step = strong acid)

OH --> Br

HBr and H2SO4 acid; use PBr3 to minimize rearrangements

making Grignard reagant

add Mg to alkyl bromide; must use ether solvent (ex. THF)

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