organosurf - 4-3-2014 at 08:16
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 ?
Metacelsus - 5-3-2014 at 08:15
Disclaimer: Speculation
The acetone's carbonyl may be reduced instead of your substrate. Isopropanol might work.
chemrox - 5-3-2014 at 18:23
Or ether (diethyl) is a lot like THF
mnick12 - 5-3-2014 at 21:44
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.