roethylsutfonates (also known as mesylates, MsOR) and p-toluenesultfonates (also
ID: 579947 • Letter: R
Question
roethylsutfonates (also known as mesylates, MsOR) and p-toluenesultfonates (also known as tosylates, TsOR) are important groups in organic synthesis. The structures of methvisulfonic acid (MsOH) and p-toluenesulfonic acid (TsOH) are given. Do you expect MsOH or TsOH to have a lower pKa and why? OH 2. Do you expect methylsulfonic acid or methylphosphonic acid to have a lower pKa and why? methylphosphonic methylsulfonic acid acid p-toluenesulfonic acid 3. Halogenated organic acids tend to be more acidic, yet we usually don't draw resonance structures with double bonds to halogens. How do we account for this increased acidity when resonance does not distribute negative charge to the halogen?Explanation / Answer
1. TsOH has lower pka since it is more acidic than MsOH. Since former one is more stabilized by resonance after deprotonation.
Methyl sulfonic acid have lower pka since more acidic due to more electronegativity of sulfur, and it pulls the electrons easily.
3. It is explained by negative Inductive effect of halogens.
Related Questions
Navigate
Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.