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Use this tag for questions relating to organic molecules and their properties (structure of organic molecules, spectroscopic properties, reaction mechanisms, stereochemistry etc). DO NOT use this tag as the only tag in your question, as this tag by itself cannot appropriately classify your question. Always use this tag in addition to other more specific tags.

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Why is this intermediate borane-hydroperoxide adduct unstable?

Basically an intermediate form, that fulfills the octet rule, would be more stable than the trialkylborane, but only if we suppose that there are no other effects! And if there were no other ffects, i …
Sam's user avatar
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7 votes
1 answer
909 views

Hydroboration on Limonene

I saw that the hydroboration of Limonene (1-Methyl-4-(1-methylethenyl)-cyclohexene) does only happen on the methylethenyl group. Up to now, I wasn't able however to find out why. Generally speaking, a …
Sam's user avatar
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8 votes
1 answer
698 views

Explaining stereochemistry in a sigmatropic 1,3-alkyl migration

I have quite a bit of difficulty in explaining sigmatropic rearrangement reactions. Consider the following reaction: How do I explain the formation of the shown product? When simply moving the elec …
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10 votes
1 answer
2k views

Reaction mechanism for the synthesis of 9,10-phenanthrenequinone

In my lab course I had to synthesize 9,10-phenanthrenequinone (phenanthrene-9,10-dione) from phenanthrene and chromium(VI) oxide. The synthesis was made as explained in Organic Syntheses, Coll. Vol. 4 …
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4 votes
0 answers
142 views

CuAAC "Click" reaction giving inconsistent results

I apologize in advance for the large amount of text and thank all those who take the time to read it. The "Click" reaction after Fokin and Sharpless is known to achieve high yields without long rea …
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5 votes
1 answer
130 views

Stubborn CuAAC reaction as derivatization for ESI-MS

Problem description I have a substance that is extremely non-polar and therefore does not ionize in the ESI source, which makes it impossible to quantify small amounts. The substance contains only two …
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