Chapter 14, Problem 58P

Interpretation Introduction

(a)

Interpretation:

The dehydrated product formed from the following alcohol with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ according to Zaitsev rule should be determined:

  

Concept Introduction:

A chemical reaction is the symbolic representation of the conversion of substances to new substances.

  $\begin{array}{l}\text{ A + B }\stackrel{}{\to }\text{ C}\\ \text{Reactant }\stackrel{}{\to }\text{ Product}\end{array}$

In a chemical reaction, the substance which is involved in conversion is said to be a reactant, whereas the newly formed substance is known as a product. Both reactants and products must be separated by an arrow.

A dehydration reaction is an elimination reaction in which a water molecule eliminates from alcohol to form alkene in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Answer to Problem 58P

  

Explanation of Solution

To get the dehydrated product of any alcohol, three steps must be followed:

• Locate the C atom in the parent chain that is bonded with −OH group.
• Eliminate H and OH group from two adjacent C's
• Add a double bond between these C's to form the product alkene.
• If there is a possibility to form two or more alkene, the major product has more C's bonded to the C=C. This is known as the Zaitsev rule.

Hence, the dehydration of 4-methylpentanol will form 4-methyl-1-pentene molecule.

 

Interpretation Introduction

(b)

Interpretation:

The dehydrate product formed from the following alcohol with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ according to Zaitsev rule should be determined:

  

Concept Introduction:

A chemical reaction is the symbolic representation of the conversion of substances to new substances.

  $\begin{array}{l}\text{ A + B }\stackrel{}{\to }\text{ C}\\ \text{Reactant }\stackrel{}{\to }\text{ Product}\end{array}$

In a chemical reaction, the substance which is involved in conversion is said to be reactant whereas the newly formed substance is known as a product. Both reactants and products must be separated by an arrow.

A dehydration reaction is an elimination reaction in which a water molecule eliminates from alcohol to form alkene in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Answer to Problem 58P

  

Explanation of Solution

To get the dehydrated product of any alcohol, three steps must be followed;

• Locate the C atom in the parent chain that is bonded with −OH group.
• Eliminate H and OH group from two adjacent C's
• Add a double bond between these C's to form the product alkene.
• If there is a possibility to form two or more alkene, the major product has more C's bonded to the C=C. This is known as the Zaitsev rule.

Hence, the dehydration of given alcohol will form only one alkene as all H next to −OH are the same.

  

Interpretation Introduction

(c)

Interpretation:

The dehydrated product formed from the following alcohol with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ according to Zaitsev rule should be determined:

  

Concept Introduction:

A chemical reaction is the symbolic representation of the conversion of substances to new substances.

  $\begin{array}{l}\text{ A + B }\stackrel{}{\to }\text{ C}\\ \text{Reactant }\stackrel{}{\to }\text{ Product}\end{array}$

In a chemical reaction; the substance which is involved in conversion is said to be reactant whereas the newly formed substance is known as a product. Both reactants and products must be separated by an arrow.

A dehydration reaction is an elimination reaction in which a water molecule eliminates from alcohol to form alkene in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Answer to Problem 58P

  

Explanation of Solution

To get the dehydrated product of any alcohol, three steps must be followed:

• Locate the C atom in the parent chain that is bonded with −OH group.
• Eliminate H and OH groups from two adjacent C's.
• Add a double bond between these C's to form the product alkene.
• If there is a possibility to form two or more alkene, the major product has more C's bonded to the C=C. This is known as the Zaitsev rule.

Hence, the dehydration of 2-octanol can form two alkenes as both the neighbor C of OH group have H atoms. Hence, dehydration of 2-octanol will follow Zaitsev rule and will form 2-octene as the major product and 1-octene as a minor product as 2-octene is more substituted alkene than 1-octene.

  

Interpretation Introduction

(d)

Interpretation:

The dehydrate product formed from the following alcohol with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ according to Zaitsev rule should be determined:

  

Concept Introduction:

A chemical reaction is the symbolic representation of the conversion of substances to new substances.

  $\begin{array}{l}\text{ A + B }\stackrel{}{\to }\text{ C}\\ \text{Reactant }\stackrel{}{\to }\text{ Product}\end{array}$

In a chemical reaction; the substance which is involved in conversion is said to be reactant whereas the newly formed substance is known as a product. Both reactants and products must be separated by an arrow.

A dehydration reaction is an elimination reaction in which a water molecule eliminates from alcohol to form alkene in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Answer to Problem 58P

  

Explanation of Solution

To get the dehydrated product of any alcohol, three steps must be followed:

• Locate the C atom in the parent chain that is bonded with −OH group.
• Eliminate H and OH group from two adjacent C's
• Add a double bond between these C's to form the product alkene.
• If there is a possibility to form two or more alkene, the major product has more C's bonded to the C=C. This is known as the Zaitsev rule.

Hence the dehydration of given alcohol can form two alkenes as both the neighbor C of OH group have H atoms. Hence dehydration of 1-methylcyclopentanol will follow Zaitsev rule and will form 1-methylcyclpentene as the major product and methylenecyclopentane as a minor product, as 1-methylcyclpentene is more substituted alkene than methylenecyclopentane.