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The detailed (and as complete as possible) description of plausible or observable pathways leading from reactants to products of a chemical process. This tag should be applied to questions about these processes. It may be applied to hypothetical and/or proposed mechanisms.

1 vote
0 answers
526 views

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 like it ought to …
gannex's user avatar
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12 votes
Accepted

Fluorescein synthesis

This reaction is considered a modified Friedel-crafts acylation. The reaction is formally a series of electrophilic aromatic substitutions, with hydroxyl leaving groups picking up protons (1), however …
gannex's user avatar
  • 2,374
4 votes
3 answers
964 views

What is the mechanism of addition of glycine into 5-chloro-N-methylisatoic anhydride?

The following transformation is involved in a step in the synthesis of diazepam: (†) What is the mechanism of the transformation from the second to the third intermediate (N-methylisatoic anhydride …
gannex's user avatar
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2 votes

What is the mechanism of addition of glycine into 5-chloro-N-methylisatoic anhydride?

I came up with this, but DHMO proposed the same mechanism first.
gannex's user avatar
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1 vote

Which is the better leaving group in the following Cannizzaro reaction?

If you'd like to read more about this mechanism, you should out this paper: Swain, C. G.; Powell, A. L.; Sheppard, W. A.; Morgan, C. R. Mechanism of the Cinazzaro Reaction, 1979, Am. Chem. Soc. 3576 …
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