Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 1, Problem 1.49P

Draw a three-dimensional representation for each molecule. Indicate which ones have a dipole moment and in what direction it is pointing.

  1. (a) CH3F
  2. (b) CH2Cl2
  3. (c) CH2ClBr
  4. (d) CFCl3
  5. (e) CCl4
  6. (f) CH2=CCl2
  7. (g) CH2=CHCl
  8. (h) HC≡C—C≡CH
  9. (i) CH3C≡N
  10. (j) (CH3)2C=O
  11. (k) BrCH=CHBr (two answers)

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  1

Fluoromethane is polar molecule because it has more electronegativity fluorine atom. The structure of fluoromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  2

Fluorine is more electronegative than carbon and hydrogen. Carbon is more electronegative than hydrogen.

The direction of dipole moment in dichloromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  3

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  4

Figure 1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  5

Dichloromethane is polar molecule because it has more electronegativity chlorine atom. The structure of dichloromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  6

Chlorine is more electronegative than carbon and hydrogen. Carbon is more electronegative than hydrogen.

The direction of dipole moment in dichloromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  7

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  8

Figure 2

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  9

Bromochloromethane is polar molecule because it has more electronegativity chlorine and bromine atom. The structure of Bromochloromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  10

Chlorine is more electronegative than carbon and hydrogen, similarly bromine is more electronegative than carbon and hydrogen. Carbon is more electronegative than hydrogen.

The direction of dipole moment in Bromochloromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  11

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  12

Figure 3

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  13

Trichlorofluoromethane is polar molecule because it has more electronegativity fluorine atom and chlorine atom. The structure of Trichlorofluoromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  14

Fluorine is more electronegative than chlorine and carbon, similarly chlorine is more electronegative than carbon.

The direction of dipole moment in Trichlorofluoromethane is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  15

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  16

Figure 4

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  17

Carbon tetrachloride is polar molecule because it has more electronegativity chlorine. The structure of Carbon tetrachloride is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  18

Chlorine is more electronegative than carbon. The direction of dipole moment in Carbon tetrachloride is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  19

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  20

Figure 5

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  21

Vinylidene chloride is polar molecule because it has more electronegativity chlorine. The structure of Vinylidene chloride is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  22

Chlorine is more electronegative than carbon and hydrogen, similarly Carbon is more electronegative than hydrogen.

The direction of dipole moment in Vinylidene chloride is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  23

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  24

Figure 6

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  25

Vinyl chloride is polar molecule because it has more electronegativity chlorine. The structure of Vinyl chloride is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  26

Chlorine is more electronegative than carbon and hydrogen, similarly Carbon is more electronegative than hydrogen.

The direction of dipole moment in Vinyl chloride is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  27

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  28

Figure 7

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is non-polar molecule. The structure of compound is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  29

Carbon is more electronegative than hydrogen.

The direction of dipole moment in of the given compound is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  30

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  31

Figure 8

(i)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  32

Acetonitrile is polar molecule because it has more electronegativity nitrogen atom. The structure of Acetonitrile is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  33

Nitrogen is more electronegative than carbon and hydrogen, similarly Carbon is more electronegative than hydrogen.

The direction of dipole moment in acetonitrile is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  34

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  35

Figure 9

(j)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  36

Acetone is polar molecule because it has more electronegativity oxygen atom. The structure of acetone is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  37

Oxygen is more electronegative than carbon and hydrogen, similarly Carbon is more electronegative than hydrogen.

The direction of dipole moment in acetone is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  38

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  39

Figure 10

(k)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Three-dimensional representation for the molecule has to be drawn and dipole movement, the direction of its dipole moment has to be identified.

Concept introduction:

Polar Molecules:

Polar Molecules contains partial positive and partial negative charge in the molecule due its electronegativity difference between the molecules.

Dipole moment:

The charge separation of the molecule produces dipole moment. Dipole moment arises between two ions in an ionic bond or covalent bond.

Dipole moment depends on the differences in electronegativity of the atom in the molecule. The electronegativity is more, the larger the dipole moment. The dipole moment is calculated from the polarity of the molecule.

Explanation of Solution

The given compound 1,2-Dibromoethylene, therefore it has two form

  1. (i) Cis 1,2-Dibromoethylene
  2. (ii) Trans- 1,2-Dibromoethylene

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  40

1,2-Dibromoethylene is polar molecule because it has more electronegativity bromine atom. The structure of 1,2-Dibromoethylene is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  41

Bromine is more electronegative than carbon and hydrogen, similarly Carbon is more electronegative than hydrogen.

The direction of dipole moment in 1,2-Dibromoethylene is given below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  42

The Three-dimensional representation for the molecule is shown below,

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  43

Figure 11

Organic Chemistry, Chapter 1, Problem 1.49P , additional homework tip  44

Figure 12

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Chapter 1 Solutions

Organic Chemistry

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