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c) + + CH₂=CH-N CH₂=CH-N O: + d) CH₃-C CH₃-C + e) The unshared electron pair on the carbon is conjugated with one of the pi bonds of the triple bond. The p orbitals of the other pi bond are perpendicular to these orbitals and are not involved in resonance. H-C=C=CH₂ 3.25 a) The N has six electrons in the structure in the middle and it has ten in the structure on the right. Both structures violate the octet rule. b) The second structure is not a resonance structure for the first structure because a hydrogen has moved. These structures represent constitutional isomers. c) The N atom in the second structure has only six electrons. d) The second structure has ten electrons at one carbon. 3.26 a) All of these resonance structures are important. Although the carbocation is unstable because it does not satisfy the octet rule at one C, it is much more stable than most carbocations because it has a large amount of resonance stabilization. + + CH₂ CH₂ CH₂ CH₂ CH₂ + + + 38

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