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Chapter 8: Q4P (page 318)

Which species in each pair is more stable?

Short Answer

Expert verified

a)

Less stable because the positive charge is shared by two primary allylic carbons.

More stable because the positive charge is shared by two primary allylic and secondary allylic carbons.

b)

Less stable because charge is on primary allylic carbon.

More stable because charge is on secondary allylic carbon.

Less stable because negative charge is not delocalized.

More stable because negative charge is delocalized.

Less stable, because positive charge is shared by both O and N.

More stable, because positive charge is shared by two nitrogens. Nitrogen is less electronegative than oxygen , so nitrogen is more comfortable with a positive charge.

Step by step solution

01

Reason behind this 

a)

Less stable because the positive charge is shared by two primary allylic carbons.

More stable because the positive charge is shared by two primary allylic and secondary allylic carbons.

b)

Less stable because charge is on primary allylic carbon.

More stable because charge is on secondary allylic carbon.

Less stable because negative charge is not delocalized.

More stable because negative charge is delocalized.

Less stable, because positive charge is shared by both O and N.

More stable, because positive charge is shared by two nitrogens. Nitrogen is less electronegative than oxygen , so nitrogen is more comfortable with a positive charge.

02

Final answer

More stable because the positive charge is shared by two primary allylic and secondary allylic carbons.

More stable because charge is on secondary allylic carbon.

c)

d)

More stable, because positive charge is shared by two nitrogens. Nitrogen is less electronegative than oxygen , so nitrogen is more comfortable with a positive charge.

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Most popular questions from this chapter

Following the instructions for drawing the energy levels of the molecular orbitals for the compounds shown in Figure 8.17, draw the energy levels of the molecular orbitals for the cycloheptatrienyl cation, thecycloheptatrienyl anion, and the cyclopropenyl cation. For each compound, show the distribution of the 蟺 electrons. Which of the compounds are aromatic?

Rank the indicated hydrogen in the following compounds from most acidic to least acidic:

Explain why the following compounds are not optically active:

a. the product obtained from the reaction of 1,3-butadiene with cis-1,2-dichloroethene

b. the product obtained from the reaction of 1,3-butadiene with trans-1,2-dichloroethene

a. In what direction is the dipole moment in fulvene? Explain.

b. In what direction is the dipole moment in calicene? Explain.

The acid dissociation constant (Ka) for loss of a proton from cyclohexanol is 1 脳10-16.

a. Draw a reaction coordinate diagram for loss of a proton from cyclohexanol.

b. Draw the resonance contributors for phenol.

c. Draw the resonance contributors for the phenolate ion.

d. On the same plot with the energy diagram for loss of a proton from cyclohexanol, draw an energy diagram for loss of a proton from phenol.

e. Which has a greater Ka: cyclohexanol or phenol?

f. Which is a stronger acid: cyclohexanol or phenol?
See all solutions

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