Problem: CL-20 and HMX are both powerful explosives. CL-20 produces a more powerful blast but is generally considered too shock-sensitive for practical use. HMX is significantly less sensitive and is used as a standard military explosive. When a 2:1 mixture of the two compounds is cocrystallized, the resulting explosive is expected to be more powerful than HMX alone, but with a sensitivity similar to HMX (Cryst. Growth Des. 2012, 12, 4311–4314). (b) Consider the lone pair of electrons on one of the nitrogen atoms within the ring(s) for either molecule. Is the lone pair localized or delocalized? 

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CL-20 and HMX are both powerful explosives. CL-20 produces a more powerful blast but is generally considered too shock-sensitive for practical use. HMX is significantly less sensitive and is used as a standard military explosive. When a 2:1 mixture of the two compounds is cocrystallized, the resulting explosive is expected to be more powerful than HMX alone, but with a sensitivity similar to HMX (Cryst. Growth Des. 201212, 4311–4314)

(b) Consider the lone pair of electrons on one of the nitrogen atoms within the ring(s) for either molecule. Is the lone pair localized or delocalized? 

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Based on our data, we think this problem is relevant for Professor ZHAO's class at ISU.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.