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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.

6 votes
1 answer
289 views

Why does LiAlH(O-tert-Bu)3 not reduce acyl chlorides to alcohols?

Why do $\ce{LiAlH(O-^{t}Bu)3}$ and similar bulky reducing agents not reduce acidic chlorine further? $$\ce{CH3-COCl + LiAlH4 + H2O -> CH3-CH=O -> CH3-CH2-OH},$$ but $$\ce{CH3-COCl + LiAlH(O-^{t}Bu)3 …
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  • 451
3 votes
1 answer
11k views

How to determine optical activity of a compound without asymmetric carbons theoretically? [closed]

I know that a compound doesn't need to have a chiral carbon to be optically active. So how can I find out whether a compound drawn on paper is chiral without access to any experiments? e.g. 1,2,2-trib …
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  • 451
9 votes

Electron withdrawing groups and acidity

Yes and no, with more electron withdrawing groups at ortho and para positions would certainly increase acidity but other factors do play a role. For example, In trinitrobenzoic acid here the two $\ …
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  • 451
16 votes
3 answers
7k views

Why does bromine add to a double bond instead of a triple bond if both are present?

According to my textbook, the addition of bromine to pent-1-en-4-yne at low temperature yields 4,5-dibromopent-1-yne: Why does bromination of the double bond occur selectively?
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