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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.

3 votes

Why Birch reduction of alkyne is E-selective?

It's not rotation but inversion (remember amine lone pair inversion) from a linear $sp$ form to trigonal planar $sp^2$ that occurs. Lone pair and radical electron are held close to atom and repulse …
Eliot Behr's user avatar
2 votes
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581 views

Why do alkyl substituents stabilize alkenes?

My textbook states that because $sp^2-sp^3$ bonds are stronger than $sp^3-sp^3$ bonds, alkenes are more stable than alkanes. The rule given is that bonds with more $s$ character are stronger. However …
Eliot Behr's user avatar
3 votes
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531 views

If alkyl-substituted alkenes are more stable, how does one explain their increased addition ...

My understanding is that in alkyl-substituted alkenes there is hyperconjugation between $𝜎(\ce{C−X})$ and $𝜋^∗(\ce{C=C})$. I also have read that more alkyl-substituted alkenes are many folds more re …
Eliot Behr's user avatar