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Nucleophilic substitution

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Kris Jones

on 15 March 2012

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Transcript of Nucleophilic substitution

Nucleophillic Substitution Conclusion we all know that dipoles exsist because last lesson we were doing some hardcore chem-cooking What is it? Why is this relevant? and each end has positive and negative polarities due to electronegativity i hope someones done cakes this week :/ we were cooking some delicious brews of 1-bromobutane so we started off wtih the butan-1-ol then chucked in some water and sodium bromide C-C-C-C-OH - H - - - - - - - - H H H H H H H H H H O Na Br just incase you didn't know ;) then after adding the magic ingredient of sulphuric acid concentrated acid plus sodium bromide = hydrogen bromide :) this is when the magic happens C-C-C-C-OH - H - - - - - - - - H H H H H H H H because the bromide ion in hyrdogen bromide is more elctronegative than the hydroxide group when it approaches the butan-1-ol it strongly attracts the positive end of the molucule with its lone pairs dragging elctrons away from the hydroxide bond towards itself until evntually bye bye hydroxide hello bromine Na-Br C-C-C-C-Br - H - - - - - - - - H H H H H H H H [Na] [OH] this for thoose who didnt guess this is 1-bromobutane out with the old and in with the new due to densities theese then seperate into the layers seen :) leaving sodium and hydroxide ions sulphuric acid and water left in our beaker as well as unreacted bromobutane and possibly unreacted sodium bromide new shiny sodium and hydroxide ions Chemistry, Its wizard ;) lets end on a nostalgic song shall we? - - obviously thisd is no good so we must try to purify this. we do this by distillation there are two types of theese reactions SN1 or SN2 which litereally refers to the number of reagents involved in the reaction so for the moment we're only concerned with SN2 then the brown gunky layer dissapers we then suck out the organice layer witha pippete so we only have organic stuff left (phew were getting there) on our way to purity :D we then added HCL and shook, this neutalised the loose hydroxide ions to produce sodium chloride and water :) that and butan-1-ol is more soluble in HCl than in water so any remaining butan-i-ol will dissolve into the hcl to be removed later residue of HCl is then removed again by adding NaHCO this is done by neutralisation again 3 seperate off the dense organic layer again (the rest of it being aquoes thus in water is less dense) add the anyhdrous NaSO this absorbs the water to produce hydrated NaSO .5H O 4 4 2 this is better than free radical substitution because then the bromide ion would attatch to any of the carbons multiple times i managed to work out the amount of 1-bromobutane i produced and percentage yeild but unfortunatley because wizard robes dont have pockets i have kinda lost it tso to make up for it well go straight to the LOTR references :) we use NaHCO because sueing something like NaOH would be silly because that would cause more substitution reactions creating alkenes (which we do not want :S) C C C - - - - - - - - - - Br H H H H H H H OH - C C C - - - - - - - - - H H H H H H H O 2 Br - &
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