(a) Interpretation: The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated. Concept introduction: Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 ° .

Question

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Answer 1

Question

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain

Conclusion

The structure of cyclodecyne is shown in Figure 2.

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain and large ring size of cyclodecyne.

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Answer 2

Question

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain

Conclusion

The structure of cyclodecyne is shown in Figure 2.

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain and large ring size of cyclodecyne.

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Answer 3

Question

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain

Conclusion

The structure of cyclodecyne is shown in Figure 2.

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain and large ring size of cyclodecyne.

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Answer 4

Question

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain

Conclusion

The structure of cyclodecyne is shown in Figure 2.

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain and large ring size of cyclodecyne.

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Answer 5

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain

Conclusion

The structure of cyclodecyne is shown in Figure 2.

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain and large ring size of cyclodecyne.

Answer 6

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Answer 7

Chapter 14, Problem 14.1P

Interpretation Introduction

(a)

Interpretation:

The model of cyclohexyne is to be built. An explanation for the instability of cyclohexyne structure is to be stated.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °.

Answer 8

Expert Solution

Answer to Problem 14.1P

The model of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 1

Cyclohexyne is unstable because of the ring strain due to the reduced bond angle in six carbon cyclic structure.

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclohexyne is a cyclic compound of six carbon atoms and contains one triple bond. The structure of cyclohexyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 2

Figure 1

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced to nearly 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes unstable. Therefore, cyclohexyne is unstable.

Answer 13

Conclusion

Cycloalkynes with carbon ring less than 8 carbons is unstable due to large bond angle strain.

Answer 14

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain

Conclusion

The structure of cyclodecyne is shown in Figure 2.

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain and large ring size of cyclodecyne.

Answer 15

Interpretation Introduction

(b)

Interpretation:

The structure of cyclodecyne is to be built. The stability of cyclodecyne and cyclohexyne is to be compared.

Concept introduction:

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes due to triple bonds do not rotate and have linear geometry with bond angle 180 °. The cycloalkynes which are smaller than cyclooctynes are unstable.

Answer 16

Expert Solution

Answer to Problem 14.1P

The model of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 3

Cyclodecyne is more stable than cyclohexyne due to less bond angle strain.

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. The triple bonded carbons are sp hybridized. Alkynes have a linear geometry with bond angle of 180 °. Cyclodecyne consist of a cyclic ring of ten carbon atoms and contains one triple bond. The structure of cyclodecyne is shown below.

Organic Chemistry, Chapter 14, Problem 14.1P , additional homework tip 4

Figure 2

Cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain. In cyclodecyne, the ten membered carbon ring of is large enough to accommodate a triple bond due to its floppiness arised by carbon-carbon bond rotations.

In cyclohexyne, the six carbon atoms ring contains one carbon-carbon triple bond. The bond angle from 180 ° is reduced nearly to 60 °. Thus, the six-membered ring experiences ring strain due to small bond angle and the ring becomes more unstable. Therefore, cyclodecyne is comparatively stable than cyclohexyne because of the reduced ring strain