An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing. Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated. Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

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Answer 1

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Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <

2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Answer 2

Question

Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

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Answer 3

Question

Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

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Answer 4

Question

Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

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Answer 5

Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

Answer 6

Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

Answer 7

Chapter 17.9, Problem 17.14P

(a)

Interpretation Introduction

To determine: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing.

Interpretation: An explanation with the use of resonance forms of a sigma complex to the show that phenyl substituent should be ortho para-directing is to be stated.

Concept introduction: Benzylic carbocation is more stable than tertiary, secondary or primary carbocation.

Answer 8

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

Answer 9

(b)

Interpretation Introduction

To determine: The mono-nitration products of the given compounds.

Interpretation: The mono-nitration products of the given compound are to be stated.

Concept introduction: The nitration reaction of aromatic compound (addition of nitro group) is an example of electrophilic substitution reaction. The natures of substituent’s (electron withdrawing or electron donating group) that are already present on aromatic ring determine the positions (ortho/meta/para) for addition of nitro group.

Answer 10

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Answer 12

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Answer 13

Ch. 17.1 - Prob. 17.1P Ch. 17.2 - Prob. 17.2P Ch. 17.3 - Prob. 17.3P Ch. 17.4 - Use resonance forms to show that the dipolar sigma...Ch. 17.6A - Prob. 17.5P Ch. 17.6A - Prob. 17.6P Ch. 17.6B - Propose a mechanism for the brommation of...Ch. 17.6B - Prob. 17.8P Ch. 17.6B - Prob. 17.9P Ch. 17.7 - Prob. 17.10P

Solution Summary: The author explains that phenyl substituent should be ortho para-directing by using resonance forms of a sigma complex.

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Chapter 17 Solutions