Skip to main content
Chemistry

Return to Question

Post Closed as "Duplicate" by Mithoron, Tyberius♦, Todd Minehardt, andselisk♦, Jon Custer
Tweeted twitter.com/StackChemistry/status/1078893515055222784
added 13 characters in body; edited tags; edited title
Source Link
orthocresol
orthocresol
  • 71.9k
  • 12
  • 249
  • 423

Confused about Why is fluoride the nucleophilicity of F-most nucleophilic halide in a polar aprotic solvent.solvents?

I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents.

From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, because atoms will be less likely to share its electron density.

However, in a polar aprotic solvent, because H-bonding cannot occur, it seems as if the trend of nucleophilicity is such that F- > Cl- > Br- > I-$\ce{F- > Cl- > Br- > I-}$.

Can someone please clarify how this is possible? I would have expected F-$\ce{F-}$ to be the LEAST nucleophilic nucleophile in a polar aprotic solvent, because it is the most electronegative atom. Therefore according to the first point I learned, I thought it should be the weakest nucleophile.

All this is what I've learned through reading Kaplan's Organic Chemistry Review.

Confused about the nucleophilicity of F- in a polar aprotic solvent.

I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents.

From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, because atoms will be less likely to share its electron density.

However, in a polar aprotic solvent, because H-bonding cannot occur, it seems as if the trend of nucleophilicity is such that F- > Cl- > Br- > I-.

Can someone please clarify how this is possible? I would have expected F- to be the LEAST nucleophilic nucleophile in a polar aprotic solvent, because it is the most electronegative atom. Therefore according to the first point I learned, I thought it should be the weakest nucleophile.

All this is what I've learned through reading Kaplan's Organic Chemistry Review.

Why is fluoride the most nucleophilic halide in aprotic solvents?

I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents.

From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, because atoms will be less likely to share its electron density.

However, in a polar aprotic solvent, because H-bonding cannot occur, it seems as if the trend of nucleophilicity is such that $\ce{F- > Cl- > Br- > I-}$.

Can someone please clarify how this is possible? I would have expected $\ce{F-}$ to be the LEAST nucleophilic nucleophile in a polar aprotic solvent, because it is the most electronegative atom. Therefore according to the first point I learned, I thought it should be the weakest nucleophile.

All this is what I've learned through reading Kaplan's Organic Chemistry Review.

Source Link
lost-in-nucleophiles
lost-in-nucleophiles
  • 75
  • 2

Confused about the nucleophilicity of F- in a polar aprotic solvent.

I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents.

From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, because atoms will be less likely to share its electron density.

However, in a polar aprotic solvent, because H-bonding cannot occur, it seems as if the trend of nucleophilicity is such that F- > Cl- > Br- > I-.

Can someone please clarify how this is possible? I would have expected F- to be the LEAST nucleophilic nucleophile in a polar aprotic solvent, because it is the most electronegative atom. Therefore according to the first point I learned, I thought it should be the weakest nucleophile.

All this is what I've learned through reading Kaplan's Organic Chemistry Review.