organosurf
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Interchanging THF with Acetone ?
In a certain reaction to reduce a primary alkyl halide to its alkane, Zinc, aqueous NH4Cl in THF at room temp are employed. THF does not form any
complexes or intermediates in the reaction.
THF is a polar nonprotic solvent; so is acetone ( apart from their dielectric constants, acetone is regarded comparatively as a weak acid due to its
methylene group, etc ).
For the above reaction, can acetone be substituted for THF ?
How about using Isopropyl alcohol ( IPA ) that is used as a proton donor in some organic reductions ?
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Nicodem
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Thread Moved
4-3-2014 at 09:24 |
Metacelsus
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Disclaimer: Speculation
The acetone's carbonyl may be reduced instead of your substrate. Isopropanol might work.
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chemrox
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Or ether (diethyl) is a lot like THF
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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mnick12
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The problem is THF's oxygen is highly coordinating, making THF a pretty good ligand. Ether is acceptable as a replacement in some scenarios, but the
bp is lower and has poorer solvating power. Although none of this may matter, depending on the reaction.
Acetone might work, but it is a ketone so it may be reduced along with your halide.
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