nitelyechos Posted March 19, 2012 Share Posted March 19, 2012 i'm trying to work my way through this problem but i dont understand it. HCN is a weak acid and bromine is a good leaving group. so what i have here is a sn1 reaction. right? or is it an e1? the HCN is too weak to substitute the bromine so the bromine has to dissassociate in the first step before the CN- can attack. but what do i do then? Link to comment Share on other sites More sharing options...
hypervalent_iodine Posted March 19, 2012 Share Posted March 19, 2012 Ignore my last post, my mistake. You need to look at the reacting carbon centre - do you think a carbocation would be stable there? As for you second question, try and draw the products for both an elimination and a substitution. The answer should become fairly obvious. Link to comment Share on other sites More sharing options...
Suxamethonium Posted March 20, 2012 Share Posted March 20, 2012 I'm confused, is the starting material equivalent to 1-bromo-2,2-dimethyl-1-phenylpropane? Or is the bromine on the aromatic ring- the 'benzene root' is confusing me. Anyway, when ever I got these questions, Once I hd drawn the molecule I'ld formulate some questions in my head, for example: Are there any groups that can leave in an elimination reaction? Under what conditions would they leave? Are there any groups that can leave in a substitution reaction? What conditions?(If applicable, hard or soft nucleophiles). Are there any groups subject to electrophilic substitution reactions? Under what conditions? Label carbons 10, 20 , 30 if it helps you. Then look at the conditions in the question and try to match them up. Link to comment Share on other sites More sharing options...
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