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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

The heat of hydrogenation of 2,3-pentadiene, a cumulated diene, is 70.5 kcal/mol. What are the relative stabilities of cumulated, conjugated, and isolated dienes?

Answer the following questions for the molecular orbitals (MOs) of 1,3,5,7-octatetraene:

a. How many MOs does the compound have?

b. Which are the bonding MOs, and which are the antibonding MOs?

c. Which MOs are symmetric, and which are antisymmetric?

d. Which MO is the HOMO and which is the LUMO in the ground state?

e. Which MO is the HOMO and which is the LUMO in the excited state?

f. What is the relationship between HOMO and LUMO and symmetric and antisymmetric orbitals?

g. How many nodes does the highest-energy MO of 1,3,5,7-octatetraene have between the nuclei?

Draw the major products obtained from the reaction of one equivalent of HCl with the following compounds. For each reaction, indicate the kinetic and thermodynamic products.

a. 2,3-dimethyl-1,3-pentadiene

b. 2,4-dimethyl-1,3-pentadiene

The triphenylmethyl cation is so stable that a salt such as triphenylmethyl chloride can be isolated and stored. Why is this carbocation so stable?

Are the following pairs of structures resonance contributors or different compounds?
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