Chapter 11.5, Problem 20P

(a)

Interpretation Introduction

Interpretation:

The product obtained from the reaction of 3-pentanol with $HOCl$ have to be explained.

Concept introduction:

• Oxidation of primary alcohol first produces aldehyde. The further oxidation of aldehyde results in the formation of carboxylic acid. Oxidation of secondary alcohol results in the formation of a ketone.
• In both primary and secondary alcohols during the oxidation reaction one hydrogen atom is eliminated from the carbon atom bonded with hydroxyl group.
• Tertiary alcohol does not undergo oxidation reaction since there is no hydrogen atom is present in the carbon atom bonded with hydroxyl group

Mechanism of oxidation of alcohol by $HOCl$

1. 1. The oxygen atom in the hydroxyl group is protonated by the acid
2. 2. By an S_N2 reaction one water molecule is eliminated by the hypochlorite ion
3. 3. Hydrogen atom is eliminated from the carbon atom bonded with $O-Cl$ bond by a base present in the reaction mixture and thus $O-Cl$ bond breaks.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.

(b)

Interpretation Introduction

Interpretation:

The product obtained from the reaction of 1-pentanol with $HOCl$ have to be explained.

Concept introduction:

• Oxidation of primary alcohol first produces aldehyde. The further oxidation of aldehyde results in the formation of carboxylic acid. Oxidation of secondary alcohol results in the formation of a ketone.
• In both primary and secondary alcohols during the oxidation reaction one hydrogen atom is eliminated from the carbon atom bonded with hydroxyl group.
• Tertiary alcohol does not undergo oxidation reaction since there is no hydrogen atom is present in the carbon atom bonded with hydroxyl group

Mechanism of oxidation of alcohol by $HOCl$

1. 1. The oxygen atom in the hydroxyl group is protonated by the acid
2. 2. By an S_N2 reaction one water molecule is eliminated by the hypochlorite ion
3. 3. Hydrogen atom is eliminated from the carbon atom bonded with $O-Cl$ bond by a base present in the reaction mixture and thus $O-Cl$ bond breaks.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.

(c)

Interpretation Introduction

Interpretation:

The product obtained from the reaction of 2-methyl-2-pentanol with $HOCl$ have to be explained.

Concept introduction:

• Oxidation of primary alcohol first produces aldehyde. The further oxidation of aldehyde results in the formation of carboxylic acid. Oxidation of secondary alcohol results in the formation of a ketone.
• In both primary and secondary alcohols during the oxidation reaction one hydrogen atom is eliminated from the carbon atom bonded with hydroxyl group.
• Tertiary alcohol does not undergo oxidation reaction since there is no hydrogen atom is present in the carbon atom bonded with hydroxyl group

Mechanism of oxidation of alcohol by $HOCl$

1. 1. The oxygen atom in the hydroxyl group is protonated by the acid
2. 2. By an S_N2 reaction one water molecule is eliminated by the hypochlorite ion
3. 3. Hydrogen atom is eliminated from the carbon atom bonded with $O-Cl$ bond by a base present in the reaction mixture and thus $O-Cl$ bond breaks.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.

(d)

Interpretation Introduction

Interpretation:

The product obtained from the reaction of 2,4-hexanediol with $HOCl$ have to be explained.

Concept introduction:

• Oxidation of primary alcohol first produces aldehyde. The further oxidation of aldehyde results in the formation of carboxylic acid. Oxidation of secondary alcohol results in the formation of a ketone.
• In both primary and secondary alcohols during the oxidation reaction one hydrogen atom is eliminated from the carbon atom bonded with hydroxyl group.
• Tertiary alcohol does not undergo oxidation reaction since there is no hydrogen atom is present in the carbon atom bonded with hydroxyl group

Mechanism of oxidation of alcohol by $HOCl$

1. 1. The oxygen atom in the hydroxyl group is protonated by the acid
2. 2. By an S_N2 reaction one water molecule is eliminated by the hypochlorite ion
3. 3. Hydrogen atom is eliminated from the carbon atom bonded with $O-Cl$ bond by a base present in the reaction mixture and thus $O-Cl$ bond breaks.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.

(e)

Interpretation Introduction

Interpretation:

The product obtained from the reaction of cyclohexanol with $HOCl$ have to be explained.

Concept introduction:

• Oxidation of primary alcohol first produces aldehyde. The further oxidation of aldehyde results in the formation of carboxylic acid. Oxidation of secondary alcohol results in the formation of a ketone.
• In both primary and secondary alcohols during the oxidation reaction one hydrogen atom is eliminated from the carbon atom bonded with hydroxyl group.
• Tertiary alcohol does not undergo oxidation reaction since there is no hydrogen atom is present in the carbon atom bonded with hydroxyl group

Mechanism of oxidation of alcohol by $HOCl$

1. 1. The oxygen atom in the hydroxyl group is protonated by the acid
2. 2. By an S_N2 reaction one water molecule is eliminated by the hypochlorite ion
3. 3. Hydrogen atom is eliminated from the carbon atom bonded with $O-Cl$ bond by a base present in the reaction mixture and thus $O-Cl$ bond breaks.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.

(f)

Interpretation Introduction

Interpretation:

The product obtained from the reaction of 1,4-butanediol with $HOCl$ have to be explained.

Concept introduction:

• Oxidation of primary alcohol first produces aldehyde. The further oxidation of aldehyde results in the formation of carboxylic acid. Oxidation of secondary alcohol results in the formation of a ketone.
• In both primary and secondary alcohols during the oxidation reaction one hydrogen atom is eliminated from the carbon atom bonded with hydroxyl group.
• Tertiary alcohol does not undergo oxidation reaction since there is no hydrogen atom is present in the carbon atom bonded with hydroxyl group

Mechanism of oxidation of alcohol by $HOCl$

1. 1. The oxygen atom in the hydroxyl group is protonated by the acid
2. 2. By an S_N2 reaction one water molecule is eliminated by the hypochlorite ion
3. 3. Hydrogen atom is eliminated from the carbon atom bonded with $O-Cl$ bond by a base present in the reaction mixture and thus $O-Cl$ bond breaks.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.