Chapter 10, Problem 10.3P

Interpretation Introduction

(a)

Interpretation:

The arrangement of the compounds ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH, Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}$ in their increasing order of acidity is to be stated.

Concept introduction:

Acidity means that the ability of the compounds to dissociate and give a proton. The extent to which a compound can give a proton determines its strength of acidity. The acidity will be higher if the position from where proton has to leave the experience a good amount of electron density pull.

Inductive effect is the push or pull of electron density by a particular group. If the group is pushing the electron density away than it is an electron donating group otherwise, an electron withdrawing group.

Answer to Problem 10.3P

The increasing order of acidity for the compounds ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH, Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}$ is shown below.

$\text{Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH}$

Explanation of Solution

The compounds provided ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH, Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}$ can be arranged in their increasing order of acidity on the basis of polar effects or inductive effect.

The inductive effect decreases with the increases in the distance of the substituents from the position of observation.

In the compounds, provided the increasing order of acidity on the basis of inductive effect is shown below.

$\text{Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH}$

The acidity of these compounds is due to the presence of hydrogen in the OH group being polar.

The compound ${\text{Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH}$ is having highest acidity because it has two electron withdrawing groups in comparison to ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$ and so, it pulls more and more electron density to make hydrogen more and more polar to leave as a proton.

The compound $\text{Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}$ is having least acidity as it is having chlorine atom at a greater distance than the ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$.

Conclusion

The increasing order of acidity for the compounds ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH, Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}$ is shown below.

$\text{Cl}{\left({\text{CH}}_{\text{2}}\right)}_3\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{Cl}}_2{\text{CHCH}}_{\text{2}}\text{OH}$

Interpretation Introduction

(b)

Interpretation:

The arrangement of the compounds ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{SH, ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH},{\text{ CH}}_3{\text{CH}}_{\text{2}}\text{OH}$ in their increasing order of acidity is to be stated.

Concept introduction:

Acidity means that the ability of the compounds to dissociate and give a proton. The extent to which a compound can give a proton determines its strength of acidity. The acidity will be higher if the position from where proton has to leave the experience a good amount of electron density pull.

Inductive effect is the push or pull of electron density by a particular group. If the group is pushing the electron density away than it is an electron donating group otherwise, an electron withdrawing group.

Answer to Problem 10.3P

The increasing order of acidity for the compounds ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{SH, ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH},{\text{ CH}}_3{\text{CH}}_{\text{2}}\text{OH}$ is shown below.

${\text{CH}}_3{\text{CH}}_{\text{2}}\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{SH}$

Explanation of Solution

The compounds provided ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{SH, ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH},{\text{ CH}}_3{\text{CH}}_{\text{2}}\text{OH}$ can be arranged in their increasing order of acidity on the basis of polar effects or inductive effect.

The inductive effect decreases with the increases in the distance of the substituent from the position of observation.

In the compounds, provided the increasing order of acidity on the basis of the inductive effect is shown below.

${\text{CH}}_3{\text{CH}}_{\text{2}}\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{SH}$

The acidity of these compounds is due to the presence of hydrogen in the OH group being polar.

The compound ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{SH}$ is having the highest acidity because it is having sulfur atom which is bigger than oxygen thus, $\text{S}-\text{H}$ the bond is weaker than the $\text{O}-\text{H}$ bond.

The compound ${\text{CH}}_3{\text{CH}}_{\text{2}}\text{OH}$ is having least acidity as it is not having chlorine atom which shows –I effect or electron-withdrawing effect to make it more acidic as is there in the ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$.

Conclusion

The increasing order of acidity for the compounds ${\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{SH, ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH},{\text{ CH}}_3{\text{CH}}_{\text{2}}\text{OH}$ is shown below.

${\text{CH}}_3{\text{CH}}_{\text{2}}\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{ClCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{SH}$

Interpretation Introduction

(c)

Interpretation:

The arrangement of the compounds ${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$ in their increasing order of acidity is to be stated.

Concept introduction:

Acidity means that the ability of the compounds to dissociate and give a proton. The extent to which a compound can give a proton determines its strength of acidity. The acidity will be higher if the position from where proton has to leave the experience a good amount of electron density pull.

Inductive effect is the push or pull of electron density by a particular group. If the group is pushing the electron density away than it is an electron donating group otherwise, an electron withdrawing group.

Answer to Problem 10.3P

The increasing order of acidity for the compounds ${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$ is shown below.

${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$

Explanation of Solution

The compounds provided ${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$ can be arranged in their increasing order of acidity on the basis of polar effects or inductive effect.

The inductive effect decreases with the increases in the distance of the substituent from the position of observation.

In the compounds provided the increasing order of acidity on the basis of the inductive effect is shown below.

${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$

The acidity of these compounds is due to the presence of hydrogen in the OH group being polar.

The compound ${\text{CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$ is having highest acidity because it is having one extra oxygen atom in the formula which is pulling its electron density from the $\text{O}-\text{H}$ group and so, making it more acidic. On the other hand, the compound ${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$ is not having any electron pulling atom or group to increase the acidity of $\text{O}-\text{H}$ group.

Conclusion

The increasing order of acidity for the compounds ${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{OH, CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$ is shown below.

${\text{CH}}_3{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}<{\text{CH}}_3{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH }$