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Single bonds generally experience free rotation at room

Chapter 2, Problem 2.67

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QUESTION:

Single bonds generally experience free rotation at room temperature (as will be discussed in more detail in Chapter 4): Free rotation of single bond Nevertheless, the single bond shown below exhibits a large barrier to rotation. In other words, the energy of the system is greatly increased if that bond is rotated. Explain the source of this energy barrier. (Hint: Think about the atomic orbitals being used to form the conduit.) ! !

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QUESTION:

Single bonds generally experience free rotation at room temperature (as will be discussed in more detail in Chapter 4): Free rotation of single bond Nevertheless, the single bond shown below exhibits a large barrier to rotation. In other words, the energy of the system is greatly increased if that bond is rotated. Explain the source of this energy barrier. (Hint: Think about the atomic orbitals being used to form the conduit.) ! !

ANSWER:

Step 1 of 2

In the cationic compound, a resonance structure can be formed by moving the double

bond over.

     

This gives the bond in question a partial double bond character, and rotation around a double bond is not allowed.

 

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