What Nucleophile Reacts with Tosylated Butanol in Et3N and H3C-CN?

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SUMMARY

The reaction of tosylated butanol with triethylamine (Et3N) in H3C-CN solvent leads to the formation of but-1-ene. The process begins with the ejection of chloride from toluenesulfonyl chloride, followed by the attachment of the tosyl group to the hydroxyl oxygen of butanol. Although chloride (Cl-) is a potential nucleophile, it is not the primary nucleophile in this reaction due to steric hindrance from Et3N. Instead, Et3N acts as a base, facilitating an elimination reaction that results in the formation of but-1-ene.

PREREQUISITES
  • Understanding of nucleophilic substitution and elimination reactions
  • Familiarity with toluenesulfonyl chloride and its reactivity
  • Knowledge of acid/base reactions involving triethylamine
  • Basic organic chemistry concepts, particularly regarding alcohols and alkenes
NEXT STEPS
  • Study the mechanism of nucleophilic substitution reactions involving tosylates
  • Research the role of triethylamine as a base in organic reactions
  • Learn about elimination reactions and the formation of alkenes
  • Explore the properties and reactivity of different nucleophiles in organic synthesis
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Chemistry students, organic chemists, and anyone interested in reaction mechanisms involving tosylates and elimination reactions.

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Homework Statement


If I react butanol with toluenesulfonyl chloride (you can see that molcule here: http://sbillinghurst.files.wordpress.com/2010/03/440px-p-toluenesulfonyl_chloride_structure-svg.png) and Et3N and use H3C-CN as solvent what do I get?

The Attempt at a Solution


I know the first step is ejecting the Cl from the toluenesulfonyl chloride and then connecting the toluenesulfonyl group to the O from the butanol.
Then I deprotonoted the O with the toluenesulfonyl group with the Et3N using an acid/base reaction. I am then left with an excellent leaving group but I'm not sure what the nucleophile could be; the only good one I find is the Cl- I expulsed from the toluenesulfonyl chloride. Is that right?
 
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In Et3N there is a lone pair on N atom, which can behave as a nucleophile, but due to the three 'Et' groups, it becomes bulky and cannot act as a nucleophile. So, it acts as a base and an elimination reaction takes place, leading to the formation of but-1-ene!
 

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