ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
Question
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Chapter 8.3, Problem 8.4TIY

(a)

Interpretation Introduction

Interpretation:Whether CH3CH2CH2CH2Li 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:

  CH3OH<1°<2°<3°

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

(b)

Interpretation Introduction

Interpretation: Whether CH3CO2Na 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:

  CH3OH<1°<2°<3°

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

(c)

Interpretation Introduction

Interpretation: Whether LiN[CH( CH 3 )2]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:

  CH3OH<1°<2°<3°

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

(d)

Interpretation Introduction

Interpretation: Whether 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:

  CH3OH<1°<2°<3°

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

(e)

Interpretation Introduction

Interpretation: Whether CH3SNa 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:

  CH3OH<1°<2°<3°

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

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