Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 1, Problem 1.82P

Stalevo is the trade name for a medication used fssor Parkinson’s disease, which contains L-dopa, carbidopa, and entacapone.

Chapter 1, Problem 1.82P, 1.77 Stalevo is the trade name for a medication used fssor Parkinson’s disease, which contains

a. Draw a Lewis structure for entacapone.

b. Which C C bond in entacapone is the longest?

c. Which C C single bond is the shortest?

d. Which C N bond is the longest?

e. Which C N bond is the shortest?

f. Use curved arrows to draw a resonance structure that is an equal contributor to the resonance hybrid.

g. Use curved arrows to draw a resonance structure that is a minor contributor to the resonance hybrid.

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: A Lewis structure for entacapone is to be drawn.

Concept introduction: One should follow the given steps to draw the Lewis structure of a given skeleton structure. The first step is placing a C atom at the intersection and at the end of any two lines. The second step is addition of enough hydrogen to make each carbon atom tetravalent. The third step is providing the lone pairs to heteroatom to complete an octet.

Answer to Problem 1.82P

A Lewis structure for entacapone is,

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  1

Explanation of Solution

The given structure of entacapone is in skeleton form.

One should follow the given steps to draw the Lewis structure of a given skeleton structure. The first step is placing a C atom at the intersection and at the end of any two lines. The second step is addition of enough hydrogen to make each carbon atom tetravalent. The third step is providing the lone pairs to heteroatom to complete an octet.

Thus, a Lewis structure for entacapone is,

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  2

Figure 1

Conclusion

A Lewis structure for entacapone is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The longest CC bond in entacapone is to be identified.

Concept introduction: Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Answer to Problem 1.82P

The CH2CH3 group contains longest CC bond in entacapone (labeled by red color).

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  3

Explanation of Solution

Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Therefore, triple bonds are stronger and shorter than double bonds, which are stronger than single bonds.

The longest CC bond in entacapone is labeled by red color as shown below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  4

Figure 2

Thus, the CH2CH3 group contains longest CC bond in entacapone.

Conclusion

The CH2CH3 group contains longest CC bond in entacapone.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The shortest CC single bond in entacapone is to be identified.

Concept introduction: Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Answer to Problem 1.82P

The shortest CC single bond is attached to CN in entacapone (labeled by red color).

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  5

Explanation of Solution

Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Therefore, triple bonds are stronger and shorter than double bonds, which are stronger than single bonds.

The shortest CC single bond in entacapone is labeled by red color as shown below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  6

Figure 3

Thus, the shortest CC single bond is attached to CN in entacapone.

Conclusion

The shortest CC single bond is attached to CN in entacapone.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The longest CN bond in entacapone is to be identified.

Concept introduction: Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Answer to Problem 1.82P

The longest CN bond in entacapone is attached to CH2CH3 group (labeled by red color).

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  7

Explanation of Solution

Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Therefore, triple bonds are stronger and shorter than double bonds, which are stronger than single bonds.

The longest CN bond in entacapone is labeled by red color as shown below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  8

Figure 4

Thus, the longest CN bond in entacapone is attached to CH2CH3 group.

Conclusion

The longest CN bond in entacapone is attached to CH2CH3 group.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The shortest CN bond in entacapone is to be identified.

Concept introduction: Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Answer to Problem 1.82P

The shortest CN bond in entacapone is CN bond (labeled by red color).

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  9

Explanation of Solution

Bond length is inversely proportional to the number of electrons present between two nuclei. This means as the number of electrons present between two nuclei increases bond length becomes shorter and stronger.

Therefore, triple bonds are stronger and shorter than double bonds, which are stronger than single bonds.

The shortest CN bond in entacapone is labeled by red color as shown below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  10

Figure 5

Thus, the shortest CN bond in entacapone is CN bond.

Conclusion

The shortest CN bond in entacapone is CN bond.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: A resonance structure that is an equal contributor to the resonance hybrid in entacapone is to be drawn.

Concept introduction: The delocalization of lone pair or free electrons from one atom to another is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of compound more will its stability.

Answer to Problem 1.82P

A resonance structure that is an equal contributor to the resonance hybrid in entacapone is drawn below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  11

Explanation of Solution

The delocalization of lone pair or free electrons from one atom to another is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of compound more will its stability.

A resonance structure that is an equal contributor to the resonance hybrid in entacapone is drawn below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  12

Figure 6

Conclusion

A resonance structure that is an equal contributor to the resonance hybrid in entacapone is drawn in Figure 6.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: A resonance structure that is minor contributor to the resonance hybrid in entacapone is to be drawn.

Concept introduction: The delocalization of lone pair or free electrons from one atom to another is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of compound more will its stability.

Answer to Problem 1.82P

A resonance structure that is minor contributor to the resonance hybrid in entacapone is drawn below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  13

Explanation of Solution

The delocalization of lone pair or free electrons from one atom to another is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of compound more will its stability.

A resonance structure that is minor contributor to the resonance hybrid in entacapone is drawn below.

Organic Chemistry, Chapter 1, Problem 1.82P , additional homework tip  14

Figure 7

Conclusion

A resonance structure that is minor contributor to the resonance hybrid in entacapone is drawn in Figure 7.

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Chapter 1 Solutions

Organic Chemistry

Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Draw a second resonance structure for each...Ch. 1 - Prob. 1.14PCh. 1 - Draw a second resonance structure for nitrous...Ch. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Simplify each condensed structure by using...Ch. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - Classify each bond in the following molecules as ...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Two radioactive isotopes of iodine used for the...Ch. 1 - Prob. 1.40PCh. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each N and O atom in the...Ch. 1 - Draw one valid Lewis structure for each compound....Ch. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Draw all reasonable resonance structures for each...Ch. 1 - Prob. 1.56PCh. 1 - Rank the resonance structures in each group in...Ch. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - Predict the geometry around each indicated atom....Ch. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Each of the following condensed or skeletal...Ch. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Label the polar bonds in each molecule. Indicate...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.79PCh. 1 - The principles of this chapter can be applied to...Ch. 1 - a. What is the hybridization of each N atom in...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 1.85PCh. 1 - Prob. 1.86PCh. 1 - Prob. 1.87PCh. 1 - Prob. 1.88PCh. 1 - Prob. 1.89PCh. 1 - Prob. 1.90P
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