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Chapter 8: Q75P (page 377)

Which loses a proton more readily: a methyl group bonded to cyclohexane or a methyl group bonded to benzene?

Short Answer

Expert verified

The methyl group on benzene can lose a proton easier than the methyl group on cyclohexane.

Step by step solution

01

Reason behind this

The methyl group on benzene can lose a proton easier than the methyl group on cyclohexane because the electrons left behind on the carbon in the former can be delocalised into the benzene ring. In contrast, the electrons left behind in the other compound cannot be delocalised.

02

Final answer

The methyl group on benzene can lose a proton easier than the methyl group on cyclohexane.

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Most popular questions from this chapter

What products would be obtained from the reaction of 1,3,5-hexatriene with one equivalent of HBr? Disregard stereoisomers.

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?

Which is more soluble in water, 3-bromocyclopropene or bromocyclopropane?

Draw the products obtained from the reaction of one equivalent of HBr with one equivalent of 1,3,5-hexatriene.

a. Which product(s) will predominate if the reaction is under kinetic control?

b. Which product(s) will predominate if the reaction is under thermodynamic control?

a.Draw resonance contributors for the following species. Do not include structures that are so unstable that their contributions to the resonance hybrid would be negligible. Indicate which are major contributors and which are minor contributors to the resonance hybrid.

1.CH3CH=CHOCH3

b.Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?
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