Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 17, Problem 17.4P
Interpretation Introduction

(a)

Interpretation: The structure corresponding to given IUPAC name of a compound is to be drawn.

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

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

2. 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.

3. When the ring is substituted with different substituents, then the numbering is done on the basis of priority.

4. 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.

Expert Solution
Check Mark

Answer to Problem 17.4P

The structure corresponding to given compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  1

Figure 1

Explanation of Solution

The IUPAC name of the compound is isobutyl benzene. The parent ring is benzene. 2-methylpropyl is isobutyl group which is present on first carbon. Hence, the structure of the compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  2

Figure 1

Conclusion

The structure corresponding to given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The structure corresponding to given IUPAC name of a compound is to be drawn.

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

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

2. 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.

3. When the ring is substituted with different substituents, then the numbering is done on the basis of priority.

4. 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.

Expert Solution
Check Mark

Answer to Problem 17.4P

The structure corresponding to given compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  3

Figure 2

Explanation of Solution

The IUPAC name of the compound is o-dichlorobenzene. The parent ring is benzene. Two chlorine atoms are adjacent to each other in benzene ring. Hence, the structure of the compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  4

Figure 2

Conclusion

The structure corresponding to given compound is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The structure corresponding to given IUPAC name of a compound is to be drawn.

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

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

2. 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.

3. When the ring is substituted with different substituents, then the numbering is done on the basis of priority.

4. 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.

Expert Solution
Check Mark

Answer to Problem 17.4P

The structure corresponding to given compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  5

Figure 3

Explanation of Solution

The IUPAC name of the compound is cis-l, 2-diphenylcyclohexane. The parent compound is cyclohexane. Two phenyl groups are present on first and second carbon atom. The orientation of these rings is in the same direction. Hence, the structure of the compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  6

Figure 3

Conclusion

The structure corresponding to given compound is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The structure corresponding to given IUPAC name of a compound is to be drawn.

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

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

2. 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.

3. When the ring is substituted with different substituents, then the numbering is done on the basis of priority.

4. 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.

Expert Solution
Check Mark

Answer to Problem 17.4P

The structure corresponding to given compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  7

Figure 4

Explanation of Solution

The IUPAC name of the compound is m-bromoaniline. The parent ring is aniline. Bromine atom is present on third carbon atom i.e. meta position. Hence, the structure of the compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  8

Figure 4

Conclusion

The structure corresponding to given compound is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The structure corresponding to given IUPAC name of a compound is to be drawn.

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

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

2. 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.

3. When the ring is substituted with different substituents, then the numbering is done on the basis of priority.

4. 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.

Expert Solution
Check Mark

Answer to Problem 17.4P

The structure corresponding to given compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  9

Figure 5

Explanation of Solution

The IUPAC name of the compound is 4-chloro-1, 2-diethylbenzene. The parent ring is benzene. Chlorine atom is present on forth carbon and two ethyl groups are present on first and second carbon in benzene ring. Hence, the structure of the compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  10

Figure 5

Conclusion

The structure corresponding to given compound is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The structure corresponding to given IUPAC name of a compound is to be drawn.

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

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

2. 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.

3. When the ring is substituted with different substituents, then the numbering is done on the basis of priority.

4. 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.

Expert Solution
Check Mark

Answer to Problem 17.4P

The structure corresponding to given compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  11

Figure 6

Explanation of Solution

The IUPAC name of the compound is 3-tert-butyl-2-ethyltoluene. The parent ring is toluene. Ethyl group is present on second carbon and ethyl group is present on third carbon in benzene ring. Hence, the structure of the compound is,

Organic Chemistry, Chapter 17, Problem 17.4P , additional homework tip  12

Figure 6

Conclusion

The structure corresponding to given compound is shown in Figure 6.

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Chapter 17 Solutions

Organic Chemistry

Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 17 - 17.27 Give the IUPAC name for each compounds. a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.35PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - 17.38 How many electrons does C contain? How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.63PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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