Like this study set? Create a free account to save it.

Sign up for an account

Already have a Quizlet account? .

Create an account

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)


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


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)

Please allow access to your computer’s microphone to use Voice Recording.

Having trouble? Click here for help.

We can’t access your microphone!

Click the icon above to update your browser permissions and try again


Reload the page to try again!


Press Cmd-0 to reset your zoom

Press Ctrl-0 to reset your zoom

It looks like your browser might be zoomed in or out. Your browser needs to be zoomed to a normal size to record audio.

Please upgrade Flash or install Chrome
to use Voice Recording.

For more help, see our troubleshooting page.

Your microphone is muted

For help fixing this issue, see this FAQ.

Star this term

You can study starred terms together

Voice Recording