Chapter 4, Problem 4.43P

Interpretation Introduction

(a)

Interpretation: The explanation corresponding to the incorrect IUPAC name $2,2-\dim \text{ethyl}-4-\text{ethylheptane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The naming of substituents attached to the longest carbon chain is not in alphabetical order. The correct IUPAC name is $4-\text{ethyl}-2,2-\text{dimethylheptane}$.

Explanation of Solution

The given IUPAC name is $2,2-\dim \text{ethyl}-4-\text{ethylheptane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 1

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

The given name is $2,2-\dim \text{ethyl}-4-\text{ethylheptane}$. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. In the given name, the naming of substituent is not in alphabetical order. Therefore, the correct IUPAC name is $4-\text{ethyl}-2,2-\text{dimethylheptane}$.

Conclusion

The naming of substituents attached to the longest carbon chain is not in alphabetical order. The correct IUPAC name is $4-\text{ethyl}-2,2-\text{dimethylheptane}$.

Interpretation Introduction

(b)

Interpretation: The explanation corresponding to the incorrect IUPAC name $5-\text{ethyl}-\text{2}-\text{methylhexane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The longest carbon chain in the given IUPAC name contains seven carbon atoms instead of six carbon atoms. The correct IUPAC name is $2,5-\text{dimethylheptane}$.

Explanation of Solution

The given IUPAC name is $5-\text{ethyl}-\text{2}-\text{methylhexane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 2

According to the given IUPAC name, the structure contains six carbon atoms.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Thus, the correct structure for the given name is shown below.

Figure 3

The longest carbon chain in the given IUPAC name contains seven carbon atoms instead of six carbon atoms. Thus, the correct IUPAC name is $2,5-\text{dimethylheptane}$.

Conclusion

The longest carbon chain in the given IUPAC name contains seven carbon atoms instead of six carbon atoms., the correct IUPAC name is $2,5-\text{dimethylheptane}$.

Interpretation Introduction

(c)

Interpretation: The explanation corresponding to the given incorrect IUPAC name $2-m\text{ethyl}-2-\text{isopropylheptane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The longest carbon chain in the given IUPAC name contains eight carbon atoms instead of seven carbon atoms. The correct IUPAC name is $2,3,3-\text{trimethyloctane}$.

Explanation of Solution

The given IUPAC name is $2-m\text{ethyl}-2-\text{isopropylheptane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 4

According to the given IUPAC name, the structure contains seven carbon atoms.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Thus, the correct structure for the given name is shown below.

Figure 5

The longest carbon chain in the given IUPAC name contains eight carbon atoms instead of seven carbon atoms. Therefore, the correct IUPAC name is $2,3,3-\text{trimethyloctane}$.

Conclusion

The longest carbon chain in the given IUPAC name contains eight carbon atoms instead of seven carbon atoms. The correct IUPAC name is $2,3,3-\text{trimethyloctane}$.

Interpretation Introduction

(d)

Interpretation: The explanation corresponding to the given incorrect IUPAC name $1,5-\dim \text{ethylcyclohexane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The structure corresponding to the given name is incorrect because the numbering of substituents is wrong. The correct IUPAC name is $1,3-\dim \text{ethylcyclohexane}$.

Explanation of Solution

The given IUPAC name is $1,5-\dim \text{ethylcyclohexane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 6

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

The given name is $1,5-\dim \text{ethylcyclohexane}$. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

The structure corresponding to the given name is incorrect because higher number is assigned to the second methyl substituent.

Therefore, the correct structure is shown below.

Figure 7

Thus, the correct IUPAC name is $1,3-\dim \text{ethylcyclohexane}$.

Conclusion

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $1,3-\dim \text{ethylcyclohexane}$.

Interpretation Introduction

(e)

Interpretation: The explanation corresponding to the incorrect IUPAC name $1-\text{ethyl}-2,6-\dim \text{ethylcycloheptane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $2-\text{ethyl}-1,4-\dim \text{ethylcycloheptane}$.

Explanation of Solution

The given IUPAC name is $1-\text{ethyl}-2,6-\dim \text{ethylcycloheptane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 8

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

The given name is $1-\text{ethyl}-2,6-\dim \text{ethylcycloheptane}$. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent.

Therefore, the correct structure is shown below.

Figure 9

Thus, the correct IUPAC name is $2-\text{ethyl}-1,4-\dim \text{ethylcycloheptane}$.

Conclusion

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $2-\text{ethyl}-1,4-\dim \text{ethylcycloheptane}$.

Interpretation Introduction

(f)

Interpretation: The explanation corresponding to the incorrect IUPAC name $5,5,6-\text{trimethyloctane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The structure corresponding to the given name is incorrect because the numbering of substituents is wrong. The correct IUPAC name is $3,4,4-\text{trimethyloctane}$.

Explanation of Solution

The given IUPAC name is $5,5,6-\text{tri}\text{methyloctane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 10

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

The given name is $5,5,6-\text{tri}\text{methyloctane}$. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

The structure corresponding to the given name is incorrect because substituents should get lowest locant number.

Therefore, the correct structure is shown below.

Figure 11

Thus, the correct IUPAC name is $3,4,4-\text{trimethyloctane}$.

Conclusion

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $3,4,4-\text{trimethyloctane}$.

Interpretation Introduction

(g)

Interpretation: The explanation corresponding to the incorrect IUPAC name $3-\text{butyl}-2,2-\dim \text{ethylhexane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The structure corresponding to the given name is incorrect because the numbering of substituents is wrong. The correct IUPAC name is $4-\text{tert}-\text{butyloctane}$.

Explanation of Solution

The given IUPAC name is $3-\text{butyl}-2,2-\dim \text{ethylhexane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 12

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

The given name is $3-\text{butyl}-2,2-\dim \text{ethylhexane}$. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Therefore, the correct structure is shown below.

Figure 13

Thus, the correct IUPAC name is $4-\text{tert}-\text{butyloctane}$.

Conclusion

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $4-\text{tert}-\text{butyloctane}$.

Interpretation Introduction

(h)

Interpretation: The explanation corresponding to the incorrect IUPAC name $1,3-\dim \text{ethylbutane}$ is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

4. First identify the word root for the given compound.

5. The suffix used in the compound like –ene.

6. Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 4.43P

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $2-\text{methylpentane}$.

Explanation of Solution

The given IUPAC name is $1,3-\dim \text{ethylbutane}$.

The structure corresponding to the given IUPAC name is shown below.

Figure 14

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

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

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

The given name is $1,3-\dim \text{ethylbutane}$. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Therefore, the correct structure is shown below.

Figure 15

The longest carbon chain contains five carbon atoms instead of four carbon atoms.

Thus, the correct IUPAC name is $2-\text{methylpentane}$.

Conclusion

The structure corresponding to the given name is incorrect because higher number is assigned to the second substituent. The correct IUPAC name is $2-\text{methylpentane}$.