Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 8, Problem 31P

(a)

Interpretation Introduction

Interpretation:The equation to show the manner ( CH3)2CHOH can act as base and acid in solution should be written and its acidic and basic strength should be compared to methanol.

Concept introduction: In accordance with Bronsted definition an acid can act as a proton donor and a base can act as a proton acceptor. Thus in a typical acid-base reaction, the fundamental principle is a lone pair of base reaches out for an acidic proton. Similar curved arrows are used to show the movement of electrons. After deprotonation, the species left with a negative charge is referred as the conjugate base of acid while the other with a positive charge is termed conjugate acid of given base. For example;

  Organic Chemistry: Structure and Function, Chapter 8, Problem 31P , additional homework tip  1

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. Smaller the pKa more is the acidity 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 lowest pKa of theses alcohols. It can readily solvated by solvent and thus is most acidic.

(b)

Interpretation Introduction

Interpretation: The equation to show the manner CH3CHFCH2OH can act as base and acid in solution should be written and its acidic and basic strength should be compared to methanol.

Concept introduction: In accordance with Bronsted definition an acid can act as a proton donor and a base can act as a proton acceptor. Thus in a typical acid-base reaction, the fundamental principle is a lone pair of base reaches out for an acidic proton. Similar curved arrows are used to show the movement of electrons. After deprotonation, the species left with a negative charge is referred as the conjugate base of acid while the other with a positive charge is termed conjugate acid of given base. For example;

  Organic Chemistry: Structure and Function, Chapter 8, Problem 31P , additional homework tip  2

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.Smaller the pKa more is the acidity 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 lowest pKa of theses alcohols. It can readily solvated by solvent and thus is most acidic.

(c)

Interpretation Introduction

Interpretation: The equation to show the manner ( CCl3)2CH2OH can act as base and acid in solution should be written and its acidic and basic strength should be compared to methanol.

Concept introduction: In accordance with Bronsted definition an acid can act as a proton donor and a base can act as a proton acceptor. Thus in a typical acid-base reaction, the fundamental principle is a lone pair of base reaches out for an acidic proton. Similar curved arrows are used to show the movement of electrons. After deprotonation, the species left with a negative charge is referred as the conjugate base of acid while the other with a positive charge is termed conjugate acid of given base. For example;

  Organic Chemistry: Structure and Function, Chapter 8, Problem 31P , additional homework tip  3

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.Smaller the pKa more is the acidity 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 lowest pKa of theses alcohols. It can readily solvated by solvent and thus is most acidic.

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