Chapter 10, Problem ISP

(a)

Interpretation Introduction

Interpretation:

The structural formulas of the initial and final oxidation products of the given compounds are to be shown.

Concept Introduction:

The chemical oxidant has the tendency to oxidize other substances.  One of the strongest oxidizing agents is potassium permanganate which oxidizes various functional groups like alcohols, aldehydes, oxime and many more.  The chemical reaction of potassium permanganate with primary alcohols gives carboxylic acids as the final oxidation product.  The reaction of carboxylic acid with sodium hydroxide leads to the formation of sodium salt along with water, sodium hydroxide being a base neutralizes the carboxylic acid and therefore, this is the type of neutralization reaction.  The chemical substances which contain amine group, $-{\text{NH}}_2$ when reacts with the carboxylic acid results in the formation of a new chemical compound which contains the amide group, $-\text{CONH}-$.  The loss of water molecule takes place during the reaction.

Answer to Problem ISP

The structural formulas of the initial and final oxidation products of the given compounds are shown below.

Explanation of Solution

The give compound, ${\text{CH}}_3{\left({\text{CH}}_2\right)}_8{\text{CH}}_2\text{OH}$ is an alcohol with ten carbon atoms.

According to the basic chemical properties, when alcohols are treated with aqueous potassium permanganate, they undergo oxidation and initially form aldehyde which on further oxidation gives carboxylic acid as potassium permanganate is strong oxidizing agent.

The oxidation of the given compound, ${\text{CH}}_3{\left({\text{CH}}_2\right)}_8{\text{CH}}_2\text{OH}$ using aqueous potassium permanganate first leads to the formation of aldehyde.  The structural formula of the initial oxidation product is shown below.

Figure 1

The above shown initial oxidation product undergoes further oxidation and results in the formation of final oxidation product.  Thus, the structural formula of the final oxidation product is shown below.

Figure 2

(b)

Interpretation Introduction

Interpretation:

The chemical equation for the reaction occurs in part (a) between the initial reactant and the final oxidation product has to be shown.

Concept Introduction:

Same as part (a).

Answer to Problem ISP

The chemical equation for the reaction occurs in part (a) between the initial reactant and the final oxidation product is shown below.

Explanation of Solution

The initial reactant in the part (a) is the give compound, ${\text{CH}}_3{\left({\text{CH}}_2\right)}_8{\text{CH}}_2\text{OH}$ is an alcohol with ten number of carbon atoms whereas the final oxidation product in part (a) is ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$.

The initial reactant, ${\text{CH}}_3{\left({\text{CH}}_2\right)}_8{\text{CH}}_2\text{OH}$ when undergoes oxidation reaction using aqueous potassium permanganate gives rise to the formation of ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$ as the final oxidation product.  The chemical equation for the reaction occurred is shown below.

Figure 3

(c)

Interpretation Introduction

Interpretation:

The class of the product so obtained in the reaction of part (b) has to be determined.

Concept Introduction:

Same as part (a).

Answer to Problem ISP

The class of the product so obtained in the reaction of part (b) is carboxylic acid.

Explanation of Solution

The initial reactant, ${\text{CH}}_3{\left({\text{CH}}_2\right)}_8{\text{CH}}_2\text{OH}$ when undergoes oxidation reaction using aqueous potassium permanganate gives rise to the formation of ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$ as the final oxidation product.

The molecular formula of the product so obtained in part (b) contains  $-\text{COOH}$ as a functional group which indicates that the product belongs to the class of carboxylic acid.

(d)

Interpretation Introduction

Interpretation:

The chemical equation for the reaction between the final product in part (b) and sodium hydroxide has to be determined.  Also, the product of the reaction when it takes place in acidic condition has to be determined.

Concept Introduction:

Same as part (a).

Answer to Problem ISP

The chemical equation for the reaction between the final product in part (b) and sodium hydroxide is,

The product of the reaction when it takes place in acidic condition is shown below.

  ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}\stackrel{{\text{H}}_{\text{2}}\text{O}}{\to }{\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2{\text{COO}}^{-}+{\text{H}}_3{\text{O}}^{+}$

Explanation of Solution

The chemical formula of the final product of part (b) is ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$.  Since ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$ belongs to the class of carboxylic acid when treated with sodium hydroxide leads to the formation of sodium salt along with water.  Sodium decanoate is formed by the neutralization reaction of decanoic acid and sodium hydroxide.

The chemical equation for the reaction between the final product of part (b) and sodium hydroxide is shown below.

Figure 4

The dissociation of ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$ will takes place when the reaction is carried out in acidic conditions.  The decanoic acid will get dissociate into decanoate ion and hydronium ion.  The chemical equation for the dissociation reaction of ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}$ is shown below.

  ${\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2\text{COOH}\stackrel{{\text{H}}_{\text{2}}\text{O}}{\to }{\text{CH}}_3{\left({\text{CH}}_2\right)}_7{\text{CH}}_2{\text{COO}}^{-}+{\text{H}}_3{\text{O}}^{+}$

(e)

Interpretation Introduction

Interpretation:

The structural formula for the product of the reaction when final oxidation product in part (a) reacts with dimethlyamine has to be determined.  Also the class of the compound so formed has to be determined.

Concept Introduction:

Same as part (a).

Answer to Problem ISP

The structural formula for the product of the reaction when final oxidation product in part (a) reacts with dimethlyamine is,

The molecular formula of the product so obtained in the above reaction contains  $-\text{CONH}-$ as a functional group which indicates that the product belongs to the class of amides.

Explanation of Solution

The structural formula of the final oxidation product of part (a) is shown below.

Figure 2

An amide bond is formed between a carboxylic acid and an amine.  Peptide linkage is formed between two amino acids.  The carboxylic acid group of one amino acid reacts with an amino group of another amino acid to form an amide bond by removing a water molecule.

The chemical reaction between the final oxidation productof part (a) with dimethlyamine is shown below.

Figure 5

The molecular formula of the product so obtained in the above reaction contains  $-\text{CONH}-$ as a functional group which indicates that the product belongs to the class of amides.

Thus, the structural formula of the product of the reaction of final oxidation product of part (a) with dimethlyamine is shown below.

Figure 6

(f)

Interpretation Introduction

Interpretation:

The reason whether the formation of polymer between the two reactants in part (b) has to be explained.

Concept Introduction:

Polymers are the high molecular mass compounds.  The small monomers units joined together to form large molecule and this reaction is known as polymerization reaction.  When two small molecules condense together to form a polymer with elimination of water molecule, the reaction is known as condensation polymerization.

Answer to Problem ISP

The basic condition for condensation polymerization is that there should be two different functional groups present in the same monomer or in two different monomers.  Since this basic condition or requirement is not fulfilled by the reactants of part (b).  Thus, the formation of polymer cannot takes place.

Explanation of Solution

The formation of polymer between the two reactants cannot takes place as there is only one functional group present in their structural formula.  The basic condition for condensation polymerization is that there should be two different functional groups present in the same monomer or in two different monomers.  Since this basic condition or requirement is not fulfilled by the reactants of part (b).

Thus, the formation of polymer cannot takes place.