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2 votes
0 answers
102 views

Protecting Thiol group in presence of alcohol

What protecting group can I use that will protect the thiol in the presence of an alcohol? Is there a set of conditions, or a group that I can use that is selective to the thiol over the alcohol? I am ...
Maya H's user avatar
  • 21
2 votes
1 answer
1k views

What should be the name of the given compound?

Following compound is named as (1) 6-Mercaptocyclohex-4-ene-1,3-diol (2) 1-Mercaptocyclohex-2-ene-4,6-diol (3) 1-Mercaptocyclohex-5-ene-2,4-diol (4) 4-Mercaptocyclohex-2-ene-1,5-diol As per my ...
studious's user avatar
  • 371
12 votes
3 answers
13k views

Why do tosylation and mesylation of alcohols follow different mechanisms?

Why do the tosylation and mesylation of an alcohol proceed via different mechanisms? More specifically, In tosylation, the lone pair of the alcohol attacks the sulfur in TsCl, but why does it not ...
NK Yu's user avatar
  • 651
3 votes
2 answers
3k views

Why is sodium methanethiolate still a better nucleophile than sodium methoxide when the solvent is ethanol

I'm looking at a problem where sodium methanethiolate and sodium methoxide, both in equal amounts, are being reacted with $\ce{CH3I}$ and the solvent is ethanol. I understand that sodium ...
John's user avatar
  • 149
17 votes
4 answers
33k views

Why is pyridine used when making tosyl esters from alcohols?

Tosyl chloride is used to make a hydroxyl group into a better leaving group. However, when the reaction of tosyl chloride and an alcohol occurs, a weak base such as pyridine should be used. Why?
RobChem's user avatar
  • 9,802