QuestionOrganic / E2 stereochemistry
The major product formed in the following reaction is:


- (a) Ethyl ether, retention
- (b) Ethyl ether, inversion
- (c) Alkene: Me/Me cis, H/Ph cis
- (d) Alkene: Me/Ph cis, H/Me cis
Answer: (c)
TsCl/py converts OH to OTs with retention (C–O not broken). NaOEt then does anti-periplanar E2: placing C3–H anti to OTs puts the two Me groups on the same side and Ph cis to H → alkene (c). E2 is stereospecific.