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Chapter 8: Q13P (page 334)

Which carbocation in each pair is more stable?

b. CH3OC+H2 or CH3NHC+H2

Short Answer

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a)

Step by step solution

01

Resonating structures             

a)

02

Final answer

a) The compound with delocalized electrons is more stable.

b) Nitrogen is less electronegative than oxygen then it is better able to share positive charge.

c) In order for electron delocalisation to occur, the atoms that share the pi electrons must be the same plane so their p orbitals can overlap. The two bulky tert-butyl groups do not allow enough room for the group with the positively charge carbon to be in the same plane as the benzene ring. Therefore the carbocation can't be stabilized by electron delocalization because the p orbital of the positively charge carbon can't overlap the p orbital of the benzene ring since they are not in the same plane.

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Most popular questions from this chapter

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?

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

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

What diene and what dienophile should be used to synthesize the following?

Between 1865 and 1890, other possible structures were proposed for benzene such as those shown here. Considering what nineteenth-century chemists knew about benzene, which is a better proposal for benzene鈥檚 structure, Dewar benzene or Ladenburg benzene? Why?

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