
Concept explainers
(a)
Interpretation:
The arrangement of the compounds ClCH2CH2OH, Cl2CHCH2OH, Cl(CH2)3OH 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 ClCH2CH2OH, Cl2CHCH2OH, Cl(CH2)3OH is shown below.
Cl(CH2)3OH<ClCH2CH2OH<Cl2CHCH2OH
Explanation of Solution
The compounds provided ClCH2CH2OH, Cl2CHCH2OH, Cl(CH2)3OH 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.
Cl(CH2)3OH<ClCH2CH2OH<Cl2CHCH2OH
The acidity of these compounds is due to the presence of hydrogen in the OH group being polar.
The compound Cl2CHCH2OH is having highest acidity because it has two electron withdrawing groups in comparison to ClCH2CH2OH and so, it pulls more and more electron density to make hydrogen more and more polar to leave as a proton.
The compound Cl(CH2)3OH is having least acidity as it is having chlorine atom at a greater distance than the ClCH2CH2OH.
The increasing order of acidity for the compounds ClCH2CH2OH, Cl2CHCH2OH, Cl(CH2)3OH is shown below.
Cl(CH2)3OH<ClCH2CH2OH<Cl2CHCH2OH
(b)
Interpretation:
The arrangement of the compounds ClCH2CH2SH, ClCH2CH2OH, CH3CH2OH 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 ClCH2CH2SH, ClCH2CH2OH, CH3CH2OH is shown below.
CH3CH2OH<ClCH2CH2OH<ClCH2CH2SH
Explanation of Solution
The compounds provided ClCH2CH2SH, ClCH2CH2OH, CH3CH2OH 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.
CH3CH2OH<ClCH2CH2OH<ClCH2CH2SH
The acidity of these compounds is due to the presence of hydrogen in the OH group being polar.
The compound ClCH2CH2SH is having the highest acidity because it is having sulfur atom which is bigger than oxygen thus, S−H the bond is weaker than the O−H bond.
The compound CH3CH2OH 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 ClCH2CH2OH.
The increasing order of acidity for the compounds ClCH2CH2SH, ClCH2CH2OH, CH3CH2OH is shown below.
CH3CH2OH<ClCH2CH2OH<ClCH2CH2SH
(c)
Interpretation:
The arrangement of the compounds CH3CH2CH2CH2OH, CH3OCH2CH2OH 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 CH3CH2CH2CH2OH, CH3OCH2CH2OH is shown below.
CH3CH2CH2CH2OH<CH3OCH2CH2OH
Explanation of Solution
The compounds provided CH3CH2CH2CH2OH, CH3OCH2CH2OH 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.
CH3CH2CH2CH2OH<CH3OCH2CH2OH
The acidity of these compounds is due to the presence of hydrogen in the OH group being polar.
The compound CH3OCH2CH2OH is having highest acidity because it is having one extra oxygen atom in the formula which is pulling its electron density from the O−H group and so, making it more acidic. On the other hand, the compound CH3CH2CH2CH2OH is not having any electron pulling atom or group to increase the acidity of O−H group.
The increasing order of acidity for the compounds CH3CH2CH2CH2OH, CH3OCH2CH2OH is shown below.
CH3CH2CH2CH2OH<CH3OCH2CH2OH
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Chapter 10 Solutions
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