Chapter 20, Problem 20.1P

Interpretation Introduction

(a)

Interpretation:

The structure of $\text{γ}-\text{hydroxybutyric acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$ or $-icacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $\text{γ}-\text{hydroxybutyric acid}$ is shown below.

Explanation of Solution

The given compound contains four carbon atom hydrocarbon chain which is identified by butyric acid. It is also known as butanoic acid. Since its name ends with suffix $-icacid$, it contains a carboxylic acid group. It also contains a hydroxyl group. The priority is given to carboxyl group compared to the hydroxyl group. Therefore, the numbering of the parent chain starts from the carboxyl group and $\text{γ}$ position is third carbon next to the carboxyl group carbon which is occupied by the hydroxyl group. The structure of $\text{γ}-\text{hydroxybutyric acid}$ is written as shown below.

Figure 1

Conclusion

The structure of $\text{γ}-\text{hydroxybutyric acid}$ is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The structure of $\beta ,\beta -\text{dichloropropionic acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $\beta ,\beta -\text{dichloropropionic acid}$ is shown below.

Explanation of Solution

The given compound contains three carbon atom hydrocarbon chain which is identified by propionic acid. It is also known as propanoic acid. Since its name ends with suffix $-icacid$, it contains a carboxylic acid group. It also contains a dichloro group. The priority is given to carboxyl group compared to the chlorine group. Therefore, the numbering of the parent chain starts from the carboxyl group and $\text{β}$ position is second carbon next to the carboxyl group carbon which is occupied by the chlorine group. It is dichloro group so it is marked by two $\text{β}$ positions. The structure of $\beta ,\beta -\text{dichloropropionic acid}$ is written as shown below.

Figure 2

Conclusion

The structure of $\beta ,\beta -\text{dichloropropionic acid}$ is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The structure of $\left(Z\right)-3-\text{hexenoic acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $\left(Z\right)-3-\text{hexenoic acid}$ is shown below.

Explanation of Solution

The given compound contains six carbon atom hydrocarbon chain which is identified by hexenoic acid. It is an unsaturated hydrocarbon chain. The unsaturation is present at $\text{C3}$. Since its name ends with suffix $-oicacid$, it contains a carboxylic acid group. It is named with prefix $\left(Z\right)$ which means the higher priority groups are present on the same side of the double bond. Therefore, the structure of $\left(Z\right)-3-\text{hexenoic acid}$ is written as shown below.

Figure 3

Conclusion

The structure of $\left(Z\right)-3-\text{hexenoic acid}$ is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The structure of $4-\text{methylhexanoic acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $4-\text{methylhexanoic acid}$ is shown below.

Explanation of Solution

The given compound contains six carbon atom hydrocarbon chain which is identified by hexanoic acid. Since its name ends with suffix $-oicacid$, it contains a carboxylic acid group. It also contains a methyl group. The priority is given to carboxyl group compared to the methyl group. Therefore, the numbering of the parent chain starts from the carboxyl group and methyl substituent is marked with locant number $4$. The structure of $4-\text{methylhexanoic acid}$ is written as shown below.

Figure 4

Conclusion

The structure of $4-\text{methylhexanoic acid}$ is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The structure of $1,4-\text{cyclohexanedicarboxylic acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $1,4-\text{cyclohexanedicarboxylic acid}$ is shown below.

Explanation of Solution

The given compound contains six carbon atom hydrocarbon cyclic chain which is identified by cyclohexane. Since its name ends with dicarboxylic acid which means it contain two carboxyl groups and their position is $1,4-$. The structure of $1,4-\text{cyclohexanedicarboxylic acid}$ is written as shown below.

Figure 5

Conclusion

The structure of $1,4-\text{cyclohexanedicarboxylic acid}$ is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The structure of $p-\text{methoxybenzoic acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $p-\text{methoxybenzoic acid}$ is shown below.

Explanation of Solution

The given compound contains six carbon atom aromatic hydrocarbon chain which is identified by benzoic acid. Since its name ends with suffix $-oicacid$, it contains a carboxylic acid group. It also contains a methoxy group. The priority is given to carboxyl group compared to the methoxy group. Therefore, the numbering of the parent chain starts from the carboxyl group and methoxy substituent is marked with locant number $4$. The structure of $p-\text{methoxybenzoic acid}$ is written as shown below.

Figure 6

Conclusion

The structure of $p-\text{methoxybenzoic acid}$ is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The structure of $\alpha ,\alpha -\text{dichloroadipic acid}$ is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of $\alpha ,\alpha -\text{dichloroadipic acid}$ is shown below.

Explanation of Solution

The given compound contains six carbon atom hydrocarbon chain which is identified by adipic acid. Adipic acid is also known as $\text{hexane}-1,6-\text{dioic acid}$. The carboxyl group is present at the position $1,6-$. It also contains a dichloro group. The priority is given to carboxyl group compared to the chlorine group. Therefore, the numbering of the parent chain starts from the carboxyl group and $\text{α}$ position is first carbon next to the carboxyl group carbon which is occupied by the chlorine group. It is dichloro group so it is marked by two $\text{α}$ positions. The structure of $\alpha ,\alpha -\text{dichloroadipic acid}$ is written as shown below.

Figure 7

Conclusion

The structure of $\alpha ,\alpha -\text{dichloroadipic acid}$ is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The structure of oxalic acid is to be drawn.

Concept introduction:

Carboxylic acid is a class of organic compound that contains a $-\text{COOH}$ group attached with a hydrocarbon chain. They occur widely in nature that includes amino acid, acetic acid (vinegar) and so on. Deprotonation of carboxylic acid gives carboxylate anion which is mostly present in soaps. The name of these compounds ends with a suffix $-oicacid$. Rules for writing IUPAC name from the structural formula are given below.

• First, identify the longest carbon chain.

• The next step is to identify the groups attached to the longest chain.

• Identify the position, location, and a number of the substituents bonded to the carbon chain.

• Use prefix di, tri, tetra if the same type of substituents are present.

• Name the substituents in alphabetical order.

Answer to Problem 20.1P

The structure of oxalic acid is shown below.

Explanation of Solution

The given compound contains two carbon atom hydrocarbon chain which is identified by oxalic acid. It is also known as $\text{ethane}-1,2-\text{dioic acid}$. The carboxyl group is present at the position $1,2-$. The structure of oxalic acid is written as shown below.

Figure 8

Conclusion

The structure of oxalic acid is shown in Figure 8.