(a) Interpretation: Whether the given compound is aromatic is to be stated. Concept introduction: Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with s p 2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows ( 4 n + 2 ) π electrons rule.

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Answer 1

Question

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

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When the 1î-NMR spectrum of acetone, CH3COCH3, is recorded on an instrument operating at 200 MHz, a single sharp resonance at 2.1î is seen. (a) How many hertz downfield from TMS does the acetone resonance correspond to? (b) If the 1î-NMR spectrum of acetone were recorded at 500 MHz, what would the position of the absorption be in î units? (c) How many hertz downfield from TMS does this 500 MHz resonance correspond to?

Following is the 1H-NMR spectrum of compound O, molecular formula C7H12. Compound O reacts with bromine in carbon tetrachloride to give a compound with the molecular formula C7H12Br2. The 13C-NMR spectrum of compound O shows signals at d 150.12, 106.43, 35.44, 28.36, and 26.36. Deduce the structural formula of compound O.

What is the 1H NMR data (chemical shift, integration, multiplicity (specify as singlet, doublet, triplet,etc.) of the following two compounds?

Answer 2

Question

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

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Answer 3

Question

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

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See solution

Answer 4

Question

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

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Answer 5

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

Answer 6

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Answer 7

Chapter 16, Problem 16.5P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is aromatic is to be stated.

Concept introduction:

Aromatic compounds are those compounds which follow the Huckel’s rule of aromaticity and are planar with sp2 hybridized atoms. According to Huckel’s rule, a compound is aromatic if the total number of electrons in the ring follows (4n+2)π electrons rule.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.

Concept introduction:

The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 16 - Prob. 16.1P Ch. 16 - Prob. 16.2P Ch. 16 - Prob. 16.3P Ch. 16 - Prob. 16.4P Ch. 16 - Prob. 16.5P Ch. 16 - Prob. 16.6P Ch. 16 - Prob. 16.7P Ch. 16 - Prob. 16.8P Ch. 16 - Prob. 16.9P Ch. 16 - Prob. 16.10P

Solution Summary: The author explains that aromatic compounds follow the Huckel's rule of aromaticity and are planar with sp2 hybridized atoms.

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