(a) Interpretation: In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified. Concept introduction: In 1 H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

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Answer 1

Question

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

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2. (i) List all the intermolecular forces presented in the following substances. And list these substances in order of increasing boiling point (lowest first). CH;OCH; CH3CHO C2H6 CH3COOH C2H;OH (ii) State whether each compound is polar or non-polar, explain the order of boiling points in (1). (iii) Which of these two compounds, CH;OCH; and CH;CH2OH, would be more soluble in water and why?

2. (a) Define and give one example of a geometry that is coordinatively unsaturated. (b) Define and give one example of a geometry that can be stereochemically non-rigid.

Explain why (i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride. (ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.

Answer 2

Question

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

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Answer 3

Question

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

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Answer 4

Question

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

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Answer 5

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Answer 6

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Answer 7

Chapter 16, Problem 16.2YT

Interpretation Introduction

(a)

Interpretation:

In benzene, all six H atoms are chemically equivalent. A plane of symmetry through which H atom is the mirror image of another is to be identified.

Concept introduction:

In 1H NMR the number of signals is equal to the number of types of protons in the molecule. Chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. Chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Answer 8

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Answer 9

Interpretation Introduction

(b)

Interpretation:

After rotation of benzene molecule in a way that the exchange of location of H atom on the molecule remains unchanged is to identified.

Concept introduction:

In a 1H NMR the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal, whereas the chemically nonequivalent or distinct protons absorb at different magnetic field and produce different signals. The chemically equivalent protons that can be distinguished by the atom must be the mirror image with respect to the plane of symmetry and the rotation of the entire molecule causes the atom to exchange its position but the identity of the molecule remains the same.

Answer 10

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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 all six H atoms in benzene are chemically equivalent. The plane of symmetry of the molecule is the mirror image of another.

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