Name: Organic Chemistry
Author: Bruice
ISBN: 9780135213711

Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene

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Bruice 8th Edition

Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene

문제 55

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. For each compound, show the distribution of the $π$ electrons. Which of the compounds are aromatic?

문제 55a

문제 56

What orbital do the lone-pair electrons occupy in each of the following compounds?

문제 57a

What orbitals contain the electrons represented as lone pairs in the structures of quinoline, indole, imidazole?

문제 57b

What orbitals contain the electrons represented as lone pairs in the structures of purine, and pyrimidine?

문제 59

Which of the following compounds could be protonated without destroying its aromaticity?

문제 60c

Refer to the electrostatic potential maps <IMAGE> to answer the following questions:

c. Why is the center of the electrostatic potential map of benzene more red than the center of the electrostatic potential map of pyridine?

문제 61a,b,c

Which of the following has delocalized electrons?

문제 61g,h,i

Which of the following has delocalized electrons?

문제 61j,k,l

Which of the following has delocalized electrons?

문제 62(3)

a. Draw resonance contributors for the following species, showing all the lone pairs:

b. For each species, indicate the most stable resonance contributor.

3. NO₂^-

문제 64a

Draw resonance contributors for the following ions:

문제 64d

Draw resonance contributors for the following ions:

문제 65

Draw all the products of the following reaction:

문제 66d,e

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

문제 67a,b

a. How many linear dienes have molecular formula C₆H₁₀? (Disregard cis–trans isomers.)

b. How many of the linear dienes in part a are conjugated dienes?

문제 68(14)

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.