All Questions
Tagged with organosulfur-compounds reaction-mechanism
14
questions
1
vote
1
answer
125
views
Why doesn’t the reaction between 3-mercaptopropionic acid and methyl iodide yield a methyl ester? [closed]
Problem
Answer
Question
I don’t understand why 3‐methylthiopropionic acid (X) is the correct answer. Wouldn’t sulfur and carbon have similar electronegativities?
As the consequence, isn’t it more ...
- 51
1
vote
2
answers
116
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Mechanism of deprotection of enol thioether
I was reading some enolate chemistry from Carruthers textbook and came across the selective alkylation of unsymmetrical ketones. The reaction involves blocking one alpha-position of the ketone using ...
- 371
3
votes
2
answers
139
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Mechanism of Grignard reaction with 2-(thiiran-2-yl)oxirane
What will be the final major product?
The answer is 2-(methoxymethyl)-3-(substituted methyl)thiirane:
I think $\ce{R}$ of $\ce{RMgX}$ attacks thiirane ring because negative charge on sulfur is more ...
4
votes
0
answers
1k
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Reaction mechanism of thiol to disulfide oxidation under basic conditions?
I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...
- 91
4
votes
0
answers
106
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Insertion vs epoxide formation
How can it be explained that in the first reaction mentioned below, a 7-membered ring dominates when the leaving group is nitrogen and an epoxide forms when the leaving group is dimethyl sulfide?
This ...
- 351
6
votes
1
answer
326
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Removing sulfur in Barton-Kellogg reaction without triphenylphosphine
I'm trying to understand how the sulfur was removed in the following reaction, taken from a paper by Ben Feringa:1
After some research I found out that this is a Barton-Kellogg reaction. Based on ...
- 531
5
votes
0
answers
219
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How does lansoprazole degrade in acidic conditions (mechanism)? [closed]
Can anybody help me and explain the mechanism of reaction here? And also I was wondering when disulfide bond is made, can molecule dissociate, return to the previous state and make a disulfide bond ...
- 51
1
vote
1
answer
1k
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Mustard gas hydrolysis (at a very high rate)
Explain mustard gas hydrolysis at a very high rate:
$\ce{Cl-CH2-CH2-S-CH2-CH2-Cl}$
I tried searching online but did not find this reaction anywhere. Can someone explain me the steps/mechanism of ...
user14857
1
vote
0
answers
526
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What is the mechanism for the conversion of thiourea to diazomethane?
I really want to know how this reaction works:
\begin{align}
\ce{SC(NH2)2 + 2 NH3 &-> CH2N2 + 2 NH4+ + S^2-}\\
(\ce{S=C(NH2)2 + 2 NH3 &-> H2C=N=N + S(NH4)2 })
\end{align}
This seems ...
- 2,354
12
votes
3
answers
13k
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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 ...
- 651
3
votes
1
answer
937
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In a nucleophilic substitution reaction, does the other atom to which the nucleophile is bonded matter?
For example,
1-bromopropane + $\ce{NaSH ->}$ Propanethiol + $\ce{NaBr}$
vs.
1-bromopropane + $\ce{H2S ->}$ Propanethiol + $\ce{HBr}$
Which is more valid, and why? Or are they equally valid?
- 133
11
votes
2
answers
10k
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Mozingo reduction mechanism
I have been searching for the mechanism of the Mozingo reduction on Google but I haven't found anything relevant.
Is the mechanism known? If so, what is it; if not, what hypothetical mechanisms can ...
- 1,242
17
votes
4
answers
33k
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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?
- 9,802
10
votes
1
answer
2k
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Oxidative chlorination mechanism (sulfide to sulfonyl chloride)
I cannot find much guidance in the literature. Any ideas as to what the mechanism of this reaction might be?
- 101