Consider the molecule C₄H₅N, which has the connectivity shown below. (a) After the Lewis structure for the molecule is completed, how many σ and how many π bonds are there in this molecule? (b) How many atoms in the molecule exhibit (i) sp hybridization, (ii) sp² hybridization, and (iii) sp³ hybridization?

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Deanna HettingerLv2

28 May 2020

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The azide ion, N₃^–, is linear with two N–N bonds of equal length, 1.16 Å. (a) Draw a Lewis structure for the azide ion. (b) With reference to Table 8.5, is the observed N–N bond length consistent with your Lewis structure? (c) What hybridization scheme would you expect at each of the nitrogen atoms in N₃^–? (d) Show which hybridized and unhybridized orbitals are involved in the formation of σ and π bonds in N₃^–. (e) It is often observed that σ bonds that involve an sp hybrid orbital are shorter than those that involve only sp² or sp³ hybrid orbitals. Can you propose a reason for this? Is this observation applicable to the observed bond lengths in N₃^–?

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Consider the Lewis structure shown below.

(a) Does the Lewis structure depict a neutral molecule or an ion? If it is an ion, what is the charge on the ion? (b) What hybridization is exhibited by each of the carbon atoms? (c) Are there multiple equivalent resonance structures for the species? (d) Which of the atoms in the species have p_π orbitals? (e) How many electrons are in the π system of the species?

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