HurricaneAlana
04-11-2008, 07:10 PM
It says that HBr adds anti-markovnikov to an alkene, but the conditions given are only hv... Doesn't peroxide have to be present, otherwise it should form the markovnikov product??
thanks
thanks
|
View Full Version : Achiever T1/Q82 HurricaneAlana 04-11-2008, 07:10 PM It says that HBr adds anti-markovnikov to an alkene, but the conditions given are only hv... Doesn't peroxide have to be present, otherwise it should form the markovnikov product?? thanks mddang 04-11-2008, 07:44 PM It should definitely be the mark product. bigstix808 04-12-2008, 09:56 AM It should definitely be the mark product. sorry, but you are mistaken my friend. HBr adds anti-Mark in the presence of peroxides AND ultra violet light. please review the mechanism for radical addition. HurricaneAlana 04-12-2008, 01:33 PM hmm... I just looked in my text.. the mechanism is using the hv to create to RO radicals from ROOR... I don't see anywhere it being anti-mark with JUST hv... does anyone have a sourse that shows it that way? how would that work in the mechanism? still confused :-\ doc3232 04-12-2008, 05:55 PM hmm... I just looked in my text.. the mechanism is using the hv to create to RO radicals from ROOR... I don't see anywhere it being anti-mark with JUST hv... does anyone have a sourse that shows it that way? how would that work in the mechanism? still confused :-\ Books can be wrong i agree with second poster. ultra or perox will do that. bigstix808 04-12-2008, 07:15 PM hmm... I just looked in my text.. the mechanism is using the hv to create to RO radicals from ROOR... I don't see anywhere it being anti-mark with JUST hv... does anyone have a sourse that shows it that way? how would that work in the mechanism? still confused :-\ uv light will cause HBr to form the Br* radical (initiation). the alkene will act as the nuclephile and attack the Br*. the Br* will then add to the anti-Mark carbon because the addition of the Br* creates another radical which is most stabilized in the most substituted position. Then the newly formed radical will attack another H-Br, steal its H and thus create another Br*. i hope that makes sense... this might help. sorry i dont have a text as a reference, but i made you a pretty picture:D http://image58.webshots.com/658/3/56/79/2006356790048425017zVZtjz_ph.jpg joh020340 04-12-2008, 07:39 PM If were talkin radical substitution to alkenes the bromine adds to the allylic position and the double bond is retained. bigstix808 04-12-2008, 10:06 PM i couldn't find a decent example in my orgo book, but try these... http://www.chemguide.co.uk/mechanisms/freerad/alkenehbr.html#top http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch06/ch6-4-2.html http://en.wikipedia.org/wiki/Radical_addition http://www.curvedarrowpress.com/partd/radicaladditionofhbr.html http://www.chem.uky.edu/Courses/che230/RBG/lecnotes/J11.pdf these were found by doing a quick search on google. HurricaneAlana 04-13-2008, 11:28 AM thanks! klutzy1987 04-14-2008, 07:45 AM Only in the presence of a peroxide group does HBr add anti-markovnikov and that is only HBr, HCl will not add anti-markovnikov. |