Chapter 14, Problem 14.69EP

(a)

Interpretation Introduction

Interpretation:

The structure of predominant organic product that is formed in the given reaction has to be drawn.

Concept Introduction:

Alcohols undergo halogenation reaction to give halogenated product.  Alcohols on halogenation gives halogenated product in which the hydroxyl group present in the alcohol is substituted by the halogen.  Phosphorous trihalides are useful in producing alkyl halides from alcohols.  The general reaction can be given as,

(b)

Interpretation Introduction

Interpretation:

The structure of predominant organic product that is formed in the given reaction has to be drawn.

Concept Introduction:

Dehydration reaction is the loss of water from a single reactant.  Alcohol undergoes dehydration reaction to form alkene.  Sulfuric acid acts as a catalyst for hydration of alkene at room temperature.  The same sulfuric acid acts as a dehydrating agent when treated with alcohol at high temperature.  If the reaction is carried out at a lower temperature, the loss of water molecule takes place from two molecule of reactant.  This results in the formation of ether.  Primary alcohol when treated with sulfuric acid at lower temperature ($\text{140}\text{°C}$) gives ether as the product while secondary and primary alcohol gives alkene as the main product in good yield.

(c)

Interpretation Introduction

Interpretation:

The structure of predominant organic product that is formed in the given reaction has to be drawn.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number $\text{C}-\text{O}$ bonds increase and/or number of $\text{C}-\text{H}$ bonds decrease.

In organic chemistry, reduction reaction is referred to the number $\text{C}-\text{O}$ bonds decrease and/or number of $\text{C}-\text{H}$ bonds increase.

Alcohols do undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

(d)

Interpretation Introduction

Interpretation:

The structure of predominant organic product that is formed in the given reaction has to be drawn.

Concept Introduction:

Dehydration reaction is the loss of water from a single reactant.  Alcohol undergoes dehydration reaction to form alkene.  Sulfuric acid acts as a catalyst for hydration of alkene at room temperature.  The same sulfuric acid acts as a dehydrating agent when treated with alcohol at high temperature.  If the reaction is carried out at a lower temperature, the loss of water molecule takes place from two molecule of reactant.  This results in the formation of ether.  Primary alcohol when treated with sulfuric acid at lower temperature ($\text{140}\text{°C}$) gives ether as the product while secondary and primary alcohol gives alkene as the main product in good yield.