Chapter 8.3, Problem 8.4TIY

(a)

Interpretation Introduction

Interpretation:Whether ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Li}$ can be strong base enough to deprotonate methanol should be identified.

Concept introduction: The strength of various conjugate acid-base pairs varies inversely to one another; the strong acid has a weak conjugate base and the strong base has weak conjugate acid and vice-versa.

The order of acidic strength of various alcohols is as follows:

  ${\text{CH}}_{\text{3}}\text{OH}<1°<2°<3°$

For tertiary alcohols, the steric bulk is maximum that leads to inhibition in solvation of $\text{tert-butoxide}$ ion. This, in turn,raises the ${\text{pK}}_{\text{a}}$ of corresponding tertiary alcohol and thus reduces their acidity. On the other hand, methanol has low ${\text{pK}}_{\text{a}}$ so it can readily solvated by solvent and thus is most acidic.

(b)

Interpretation Introduction

Interpretation: Whether ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{Na}$ can be strong base enough to deprotonate methanol should be identified.

Concept introduction:The strength of various conjugate acid-base pairs varies inversely to one another; the strong acid has a weak conjugate base and the strong base has weak conjugate acid and vice-versa.

The order of acidic strength of various alcohols is as follows:

  ${\text{CH}}_{\text{3}}\text{OH}<1°<2°<3°$

For tertiary alcohols, the steric bulk is maximum that leads to inhibition in solvation of $\text{tert-butoxide}$ ion. This, in turn,raises the ${\text{pK}}_{\text{a}}$ of corresponding tertiary alcohol and thus reduces their acidity. On the other hand, methanol has low ${\text{pK}}_{\text{a}}$ so it can readily solvated by solvent and thus is most acidic.

(c)

Interpretation Introduction

Interpretation: Whether $\text{LiN}{\left[\text{CH}{\left({\text{CH}}_{\text{3}}\right)}_2\right]}_2$ can be strong base enough to deprotonate methanol should be identified.

Concept introduction:The strength of various conjugate acid-base pairs varies inversely to one another; the strong acid has a weak conjugate base and the strong base has weak conjugate acid and vice-versa.

The order of acidic strength of various alcohols is as follows:

  ${\text{CH}}_{\text{3}}\text{OH}<1°<2°<3°$

For tertiary alcohols, the steric bulk is maximum that leads to inhibition in solvation of $\text{tert-butoxide}$ ion. This, in turn,raises the ${\text{pK}}_{\text{a}}$ of corresponding tertiary alcohol and thus reduces their acidity. On the other hand, methanol has low ${\text{pK}}_{\text{a}}$ so it can readily solvated by solvent and thus is most acidic.

(d)

Interpretation Introduction

Interpretation: Whether $\text{KH}$ can be strong base enough to deprotonate methanol should be identified.

Concept introduction:The strength of various conjugate acid-base pairs varies inversely to one another; the strong acid has a weak conjugate base and the strong base has weak conjugate acid and vice-versa.

The order of acidic strength of various alcohols is as follows:

  ${\text{CH}}_{\text{3}}\text{OH}<1°<2°<3°$

For tertiary alcohols, the steric bulk is maximum that leads to inhibition in solvation of $\text{tert-butoxide}$ ion. This, in turn,raises the ${\text{pK}}_{\text{a}}$ of corresponding tertiary alcohol and thus reduces their acidity. On the other hand, methanol has low ${\text{pK}}_{\text{a}}$ so it can readily solvated by solvent and thus is most acidic.

(e)

Interpretation Introduction

Interpretation: Whether ${\text{CH}}_{\text{3}}\text{SNa}$ can be strong base enough to deprotonate methanol should be identified.

Concept introduction:The strength of various conjugate acid-base pairs varies inversely to one another; the strong acid has a weak conjugate base and the strong base has weak conjugate acid and vice-versa.

The order of acidic strength of various alcohols is as follows:

  ${\text{CH}}_{\text{3}}\text{OH}<1°<2°<3°$

For tertiary alcohols, the steric bulk is maximum that leads to inhibition in solvation of $\text{tert-butoxide}$ ion. This, in turn,raises the ${\text{pK}}_{\text{a}}$ of corresponding tertiary alcohol and thus reduces their acidity. On the other hand, methanol has low ${\text{pK}}_{\text{a}}$ so it can readily solvated by solvent and thus is most acidic.