ORGANIC CHEMISTRY-MOLYMOD PACKAGE
ORGANIC CHEMISTRY-MOLYMOD PACKAGE
5th Edition
ISBN: 9781260227307
Author: SMITH
Publisher: MCG
Question
Chapter 1, Problem 1.68P
Interpretation Introduction

(a)

Interpretation: The shortest CC single bond is to be labeled.

Concept introduction: There is an inverse relationship between bond length and bond strength. Shorter bonds are stronger bonds or higher the bond order, shorter is the bond length.

Expert Solution
Check Mark

Answer to Problem 1.68P

The shortest CC single bond is [2].

Explanation of Solution

In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type of hybridization. The percent s-character gives the fraction of 2s orbital which is present in a hybrid orbital. As the percent s-character increases, the bond becomes shorter and stronger. This due to the fact that a 2s orbital keeps electron density closer to a nucleus as compared to a 2p orbital.

ORGANIC CHEMISTRY-MOLYMOD PACKAGE, Chapter 1, Problem 1.68P

Figure 1

Both [1] and [2] are single CC bond as shown above. Bond [1] is formed by Csp3Csp3 hybrid orbitals and bond [2] is formed by Csp3Csp2 hybrid orbitals. Thus, bond [2] has more percent s-character. Hence, the shortest CC single bond is [2].

Conclusion

The shortest CC single bond is [2].

Interpretation Introduction

(b)

Interpretation: The longest CC single bond is to be labeled.

Concept introduction: There is an inverse relationship between bond length and bond strength. Shorter bonds are stronger bonds or higher the bond order shorter is the bond length.

Expert Solution
Check Mark

Answer to Problem 1.68P

The longest CC single bond is [1].

Explanation of Solution

In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type of hybridization. The percent s-character gives the fraction of 2s orbital which is present in a hybrid orbital. As the percent s-character increases, the bond becomes shorter and stronger. This due to the fact that a 2s orbital keeps electron density closer to a nucleus as compared to a 2p orbital. Both [1] and [2] are single bond as shown in Figure 1.Bondbut [1] is formed by Csp3Csp3 hybrid orbitals and bond [2] is formed by Csp3Csp2 hybrid orbitals. Thus, bond [1] has less percent s-character. Hence the longest CC single bond is [1].

Conclusion

The longest CC single bond is [1].

Interpretation Introduction

(c)

Interpretation: The shortest CC bond is to be labeled.

Concept introduction: There is an inverse relationship between bond length and bond strength. Shorter bonds are stronger bonds or higher the bond order shorter is the bond length.

Expert Solution
Check Mark

Answer to Problem 1.68P

The shortest CC bond is triple bond between two carbon atoms.

Explanation of Solution

In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type of hybridization. The percent s-character gives the fraction of 2s orbital which is present in a hybrid orbital. As the percent s-character increases, the bond becomes shorter and stronger. This due to the fact that a 2s orbital keeps electron density closer to a nucleus as compared to a 2p orbital. Triple bond is formed by CspCsp hybrid orbitals it has highest percent s-character among other CC bond. Hence, the shortest CC bond is triple bond.

Conclusion

The shortest CC bond is triple bond between two carbon atoms.

Interpretation Introduction

(d)

Interpretation: The weakest CC bond is to be labeled.

Concept introduction: There is an inverse relationship between bond length and bond strength. Shorter bonds are stronger bonds or higher the bond order shorter is the bond length.

Expert Solution
Check Mark

Answer to Problem 1.68P

The weakest CC bond is [1].

Explanation of Solution

In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type of hybridization. The percent s-character gives the fraction of 2s orbital which is present in a hybrid orbital. As the percent s-character increases, the bond becomes shorter and stronger. This due to the fact that a 2s orbital keeps electron density closer to a nucleus as compared to a 2p orbital..

Both [1] and [2] are single bond as shown in Figure 1.Bond [1] is formed by Csp3Csp3 hybrid orbitals and bond [2] is formed by Csp3Csp2 hybrid orbitals. Bond [1] has less percent s-character. Hence, the weakest CC bond is [1].

Conclusion

The weakest CC bond is [1].

Interpretation Introduction

(e)

Interpretation: The strongest CH bond is to be labeled.

Concept introduction: There is an inverse relationship between bond length and bond strength. Shorter bonds are stronger bonds or higher the bond order shorter is the bond length.

Expert Solution
Check Mark

Answer to Problem 1.68P

The strongest CH bond is with triple CC bond.

Explanation of Solution

The length and strength of a CH bond depends on the hybridization of the carbon atom. In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type of hybridization. The percent s-character gives the fraction of 2s orbital which is present in a hybrid orbital. As the percent s-character increases, the bond becomes shorter and stronger. This due to the fact that a 2s orbital keeps electron density closer to a nucleus as compared to a 2p orbital.

Triple bond is formed by CspCsp it has highest percent s-character among other CC bond. Hence, CH with triple CC bond has highest percent s character and is the strongest bond.

Conclusion

The strongest CH bond is with triple CC bond.

Interpretation Introduction

(f)

Interpretation: Bond [1] and [2] are of different length, even though they are both CC single bond reason is to be explained.

Concept introduction: There is an inverse relationship between bond length and bond strength. Shorter bonds are stronger bonds or higher the bond order shorter is the bond length.

Expert Solution
Check Mark

Answer to Problem 1.68P

Bond [1] and [2] are of different length, even though they are both CC single bond due to the difference in percent-s character.

Explanation of Solution

In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type of hybridization. The percent s-character gives the fraction of 2s orbital which is present in a hybrid orbital. As the percent s-character increases, the bond becomes shorter and stronger. This due to the fact that a 2s orbital keeps electron density closer to a nucleus as compared to a 2p orbital. Both [1] and [2] are single bond as shown in Figure 1. Bond [1] is formed by Csp3Csp3 hybrid orbitals and bond [2] is formed by Csp3Csp2 hybrid orbitals. Hence, bond [2] has more percent s character and is shorter in length than bond [1].

Conclusion

Bond [1] and [2] are of different length, even though they are both CC single bond due to the difference in percent-s character.

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Chapter 1 Solutions

ORGANIC CHEMISTRY-MOLYMOD PACKAGE

Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Draw a second resonance structure for each species...Ch. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Using the principles of VSEPR theory, you can...Ch. 1 - Convert each condensed formula to a Lewis...Ch. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - What is the molecular formula of quinine, the...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 - The unmistakable odor of a freshly cut cucumber is...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 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each and atom in the...Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - 1.58 Predict the geometry around each highlighted...Ch. 1 - Prob. 1.59PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 1.65PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Prob. 1.68PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 1.71PCh. 1 - Anacin is an over-the-counter pain reliever that...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.74PCh. 1 - 1.75 The principles of this chapter can be...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. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.83PCh. 1 - Prob. 1.84PCh. 1 - Prob. 1.85P
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