SME
Organic Chemistry I · Problem type
A Williamson ether synthesis, in order
Use this for “Plan a synthesis of tert-butyl methyl ether, (CH₃)₃COCH₃, from an alcohol and an alkyl halide.”
Put in order
Put the steps for making (CH₃)₃COCH₃ in order.
1
?
2
?
3
?
4
?
Assumptions
•
The alkoxide is a strong base as well as a nucleophile, so the halide must be methyl or primary for SN2 to win.
•
On a secondary or tertiary halide E2 wins: (CH₃)₃CBr with CH₃O⁻ gives mostly 2-methylpropene, not the ether.
•
NaH takes the O–H proton for good, as H₂ gas leaves; a dry solvent such as THF keeps water from taking the alkoxide back.
Topic check
See what you know: 5 questions on this topic
New questions each time. Pass to mark it complete.