Andrea93 Posted June 26, 2018 Share Posted June 26, 2018 Hi! I can't solve this question: I think it's a intramolecular Sn2 reaction But that can occor only with "trans isomer" So in the first one what is the product? Does NaOH deprotonate the -OH group or give a Sn2 reaction on the carbon bonded with Cl? (Usually acid-base reactions are faster than Sn2 ones) I have the same doubt for the last one. Some help? Thanks!! Link to comment Share on other sites More sharing options...
hypervalent_iodine Posted June 26, 2018 Share Posted June 26, 2018 For the last one, why are you ignoring the actual substrate in the reaction? Link to comment Share on other sites More sharing options...
Andrea93 Posted June 27, 2018 Author Share Posted June 27, 2018 15 hours ago, hypervalent_iodine said: For the last one, why are you ignoring the actual substrate in the reaction? Yes...but I don't know what happens The NaOH,so the OH- only deprotonates the alcoholic OH- of the substrate or gives a Sn2 reaction with the carbon bonded witch Br?? I have tue same doubt for the first one...I don't now if it is the correct product..same thing: the nucleophile OH- attacck the carbon bonded with Cl or it gives an acid-base reaction with the alcoholic group ?Or both? Thanks Link to comment Share on other sites More sharing options...
chemgreger Posted July 14, 2018 Share Posted July 14, 2018 Quote I'm new here and I know I'm a bit late, but I'm having trouble seeing why any of those reactions would be a ring closing. I know it could theoretically happen because NaOH is a strong base, but still isn't strong enough for deprotonation of those particular alcohols. I would imagine for the first you would get the trans diol. And for the second a mixture of cis diol product and the epoxide. All that assuming SN1 isn't even being considered. If anyone could help me here, I saw this and I too am a bit confused. Link to comment Share on other sites More sharing options...
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