[pecan66]

Cyanogen reacts with morpholine to form a single product A.

+   A

The spectroscopic data for A are shown below:

Carbon-13 data/ppm : 45.6, 66.2, 110.6, 142.1

IR data over 1500cm^-1/cm^-1 : 3290, 2234, 1620

Now I'm asking for help on this as I sometimes have trouble working out structures from the data in general. My attempt for this one is that I think the IR at 3290 must be either a N-H bond and so it should remain in the product. 2234 falls within the triple bond region so my guess is C#N but then I get stuck for 1620, this could either be a C=N bond or a C=O bond, my guess is that it's a C=N bond as carbonyls are usually around 1715. The problem is that I have no idea about how the reaction proceeds, I have worked out the HOMO and LUMO for both reagents but I don't know which way around they react.

Help would be much appreciated!

Thanks

[AlphaScent]

Any other conditions?  An acid? Water?

[zsinger]

Well….lets go step by step.  How would you expect the nitrogen (extra electron pair) or the oxygen (2 extra electron pairs) to react with one of the carbons (arbitrary b/c this is a symmetrical molecule).  Would the ring break?  Hope this helps.
                 -Zack

[PhDoc]

HOMO/LUMO not needed for this. What's your nucleophile? What's your electrophile? What's the likelihood a C-C bond will break to spit out a leaving group? What's the most logical intermediate you can obtain? What happens with the proton in the end?

What's your product?

If you have 6 carbons in your compound and 4 signals in your 13C, what (very fundamental) can you conclude? What functional group absorbs IR at 2234? Do all C=N bonds absorb at 1715? What happens to an IR absorption of a C=X when it's in conjugation with another group?

Please think about all this. You'll need it for any spectroscopy exam.