Chapter 17, Problem 17.28P

Draw a structure corresponding to each name.

a. $p\text{-dichlorobenzene}$

b. $p\text{-iodoaniline}$

c. $o\text{-bromonitrobenzene}$

d. $2,6\text{-dimethoxytoluene}$

e. $2\text{-phenylprop-2-en-1-ol}$

f. $trans\text{-1-benzyl-3-phenylcyclopentane}$

Interpretation Introduction

(a)

Interpretation: The structure which corresponds to the IUPAC name of the given compound is to be stated.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for benzene derivatives are:

1. The compound consists of benzene ring is named as substituent followed by benzene.

2. When the ring is mono-substituted, then there is no need of numbering.

3. When the ring is substituted with same substituents, then numbering to one substituent is given and for other substituent, numbering proceed from clockwise or anticlockwise such that it gets lower number.

4. When the ring is substituted with different substituents, then the numbering is done according to the priority.

5. Substituents on benzene ring is also indicated using ortho, meta, para prefix. The prefix ortho is used when substituents are on adjacent carbon, meta is used when substituents are separated by one carbon atom, para is used when substituents are across each other in benzene ring.

Answer to Problem 17.28P

The structure of the given compound is,

Explanation of Solution

The IUPAC name of the compound is $p\text{-dichlorobenzene}$. The parent chain consists of benzene ring. Two chlorine atoms are present at para position in the benzene ring. When same substituents are present, then prefix depends on the number of substituents. Hence, the structure of the given compound is,

Figure 1

Conclusion

The structure of the given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The structure which corresponds to the IUPAC name of the given compound is to be stated.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for benzene derivatives are:

1. The compound consists of benzene ring is named as substituent followed by benzene.

2. When the ring is mono-substituted, then there is no need of numbering.

3. When the ring is substituted with same substituents, then numbering to one substituent is given and for other substituent, numbering proceed from clockwise or anticlockwise such that it gets lower number.

4. When the ring is substituted with different substituents, then the numbering is done according to the priority.

5. Substituents on benzene ring is also indicated using ortho, meta, para prefix. The prefix ortho is used when substituents are on adjacent carbon, meta is used when substituents are separated by one carbon atom, para is used when substituents are across each other in benzene ring.

Answer to Problem 17.28P

The structure of the given compound is,

Explanation of Solution

The IUPAC name of the given compound is $p\text{-iodoaniline}$. The parent chain consists of aniline. Iodine atom and amine group present at para position in the benzene ring. Hence, the structure of the given compound is,

Figure 2

Conclusion

The structure of the given compound is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The structure which corresponds to the IUPAC name of the given compound is to be stated.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for benzene derivatives are:

1. The compound consists of benzene ring is named as substituent followed by benzene.

2. When the ring is mono-substituted, then there is no need of numbering.

3. When the ring is substituted with same substituents, then numbering to one substituent is given and for other substituent, numbering proceed from clockwise or anticlockwise such that it gets lower number.

4. When the ring is substituted with different substituents, then the numbering is done according to the priority.

5. Substituents on benzene ring is also indicated using ortho, meta, para prefix. The prefix ortho is used when substituents are on adjacent carbon, meta is used when substituents are separated by one carbon atom, para is used when substituents are across each other in benzene ring.

Answer to Problem 17.28P

The structure of the given compound is,

Explanation of Solution

The IUPAC name of the compound is $o\text{-bromonitrobenzene}$. The parent chain consists of benzene ring. Bromine atom and nitro group are present at ortho position in benzene ring. Hence, the structure of the given compound is,

Figure 3

Conclusion

The structure of the given compound is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The structure which corresponds to the IUPAC name of the given compound is to be stated.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for benzene derivatives are:

1. The compound consists of benzene ring is named as substituent followed by benzene.

2. When the ring is mono-substituted, then there is no need of numbering.

3. When the ring is substituted with same substituents, then numbering to one substituent is given and for other substituent, numbering proceed from clockwise or anticlockwise such that it gets lower number.

4. When the ring is substituted with different substituents, then the numbering is done according to the priority.

5. Substituents on benzene ring is also indicated using ortho, meta, para prefix. The prefix ortho is used when substituents are on adjacent carbon, meta is used when substituents are separated by one carbon atom, para is used when substituents are across each other in benzene ring.

Answer to Problem 17.28P

The structure of the given compound is,

Explanation of Solution

The IUPAC name of the compound is $2,6\text{-dimethoxytoluene}$. The parent chain consists of toluene. Two methoxy groups are present on second and sixth carbon atom. When same substituents are present, then prefix depends on the number of substituents. Hence, the structure of the given compound is,

Figure 4

Conclusion

The structure of the given compound is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The structure which corresponds to the IUPAC name of the given compound is to be stated.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for hydrocarbon are:

1. The hydrocarbon is named after the carbon chain containing higher number of carbon atoms.

2. Alkenes are named after their parent hydrocarbon chain with suffix ‘ene’.

3. For functional group such as alcohol suffix ‘ol’ is added to the name.

4. When the ring is substituted with different substituents, then the numbering is done according to the priority.

Answer to Problem 17.28P

The structure of the given compound is,

Explanation of Solution

The IUPAC name of the compound is $2\text{-phenylprop-2-en-1-ol}$. The parent chain consists of propanol. Phenyl group is present on second carbon atom. Double bond is present between second and third carbon atom. Hence, the structure of the given compound is,

Figure 5

Conclusion

The structure of the given compound is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The structure which corresponds to the IUPAC name of the given compound is to be stated.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for a cycloalkane are:

1. The cycloalkane is named after its parent hydrocarbon chain with a prefix cyclo.

2. When the ring is mono-substituted then there is no need of numbering.

3. When the ring is substituted with same substituents then numbering to one substituent is given and for other substituent numbering proceed from clockwise or anticlockwise such that it gets lower number.

4. When the ring is substituted with different substituents, then the numbering is done according to the priority.

5. When alkyl chain has more carbon atoms than the cycloalkane then, the substituent is named as cycloalkyl group.

Answer to Problem 17.28P

The structure of the given compound is,

Explanation of Solution

The IUPAC name of the compound is $trans\text{-1-benzyl-3-phenylcyclopentane}$. The parent chain consists of cyclopentane ring. Benzyl group and phenyl group is present on first and third carbon atom. These groups points in the opposite direction of ring. Hence, the structure of the given compound is,

Figure 6

Conclusion

The structure of the given compound is shown in Figure 6.