What is the correct order of decreasing acidi | vedclass

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(A) To determine the acidity,we look at the stability of the conjugate base formed after the loss of a proton $(H^+)$. The more stable the conjugate b

Vedclass · Accepted Answer

$IV > I > III > II$

Vedclass · Answer

(A) To determine the acidity,we look at the stability of the conjugate base formed after the loss of a proton $(H^+)$. The more stable the conjugate base,the more acidic the compound.$I$ is piperidine: The conjugate base is a secondary amide-like anion with $sp^3$ nitrogen.$II$ is pyridine: The conjugate base is a pyridyl anion with $sp^2$ nitrogen.$III$ is morpholine: The conjugate base is similar to piperidine but with an electron-withdrawing oxygen atom,which stabilizes the negative charge.$IV$ is pyrrole: The lone pair on the nitrogen is involved in aromaticity. Loss of $H^+$ from the $N$ atom results in a conjugate base where the negative charge is delocalized into the aromatic ring,making it highly stable.The order of acidity is: $IV$ (pyrrole,$pKa \approx 16.5$) > $II$ (pyridine,$pKa \approx 35$) > $I$ (piperidine,$pKa \approx 36$) > $III$ (morpholine,$pKa \approx 37$).However,in the context of common textbook problems regarding these specific nitrogen heterocycles,the acidity order is typically $IV > II > I > III$ or similar based on hybridization and resonance. Given the options provided,the correct order of decreasing acidity is $IV > I > III > II$.

What is the correct order of decreasing acidity for the following compounds?

Similar Questions

Explain the terms Inductive and Electromeric effects. Which electron displacement effect explains the following correct orders of acidity of the carboxylic acids?
$(a)$ $Cl_3CCOOH > Cl_2CHCOOH > ClCH_2COOH$
$(b)$ $CH_3CH_2COOH > (CH_3)_2CHCOOH > (CH_3)_3C \cdot COOH$

$x =$ number of compounds that are better hydride donors than $Ph-CH(O^{\Theta})_2$.

Which of the following orders correctly depicts the decreasing order of stability of carbanion?

In which type of molecule are the electrons of a $\pi$ bond delocalized?

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