10. Explain in Detail the reasoning behind your identification of this unknown.

The unknown compound is determined to be morpholine with support from the data
including classification and derivative tests, the boiling point, the IR and the NMR.
First, the classification tests show that there is an oxygen group in the compound that is
easily oxidized, because the chromic acid test was positive, but the 2,4-DNP test was negative. It
can also be concluded that the unknown is not aromatic based on the negative result of the
ignition test, which rules out some possible compounds. Finally, the nitrous acid test showed a
positive result for an amine, especially indicating a secondary amine because of the yellow film
that formed on the top of solution.
The boiling point of the compound was found to be 128 which is very close to the
literature value for morpholine of 129. This also overlaps with 2-methyl pyridine which has a
literature boiling point of 128-129. The recorded boiling point is significantly lower than any
other possible unknowns.
The derivative test of benzamide gave a melting point of 64.2-66.1. The literature melting
point for morpholine is 75, which is within 10 degrees of the recorded unknown melting point. It
is significantly greater than the melting point of n-hexylamine at 40 and very depressed from the
melting point of cyclohexyamine of 149. The other possible compounds do not have a literature
melting point for this derivative.
The IR shows an N-H stretch at 1635.0 cm and 3333.5 cm. It also shows some N-H
overtones above 3500 cm. It shows sp3 hybridized C-H bonds at 2850.3 cm and 2946.5 cm. The
IR also has a lot of interference in it indicating the ring structure seen in morpholine.
The NMR greatly supports the conclusion that the unknown is morpholine. The peaks
that are triplets at 2.858ppm and 3.675ppm show two protons that split each other, which is
reflected in the ratios of the integrals of 1:1. The peak that has a greater chemical shift must be
more deshielded and located on the carbon next to the oxygen. The broad peak at 1.95ppm
indicates the hydrogen that is connected to the amine, and is reflected in its lower chemical shift
as well and its integration of about 1 proton. The NMR clearly rules out all other possible
compounds as well because this pattern would not be formed for any of the others.
In studying the data presented here, particularly the NMR and boiling point, as well as
the list of possible unknowns in can be seen that morpholine is the best choice.
11. Explain, in detail, any results that contradict your choice and why you felt that they are (or
are not) relevant.
The results of the beilstein test somewhat contradict my conclusion, because the test was
initially thought to be positive. The green flame did not always appear thought when testing this
unknown, so it is possible that the flame was reacting with another residual compound on the
copper wire that was not properly burned off. It was also concluded that these results were not
relevant because none of the compounds that were amines within the boiling point of the
unknown has halides.
Another result that contradicts the choice of unknown is the chromic acid test. The results
of the chromic acid tests were positive, but the 2,4-DNP were negative which usually indicates
an alcohol that can be easily oxidized by the reagent such as a primary or secondary alcohol.
While there is no alcohol in this compound, it is possible that one of the heteroatoms can be
easily oxidized in a way that is outside of the scope of this class. Since the classification tests

should be taken with a grain of salt, both of the inconclusive results discussed here do not
dissuade the choice of unknown compound as morpholine.
12. Analysis of IR spectrum:
The IR shows an N-H stretch at 1635.0 cm and 3333.5 cm. It also shows some N-H
overtones above 3500 cm. It shows sp3 hybridized C-H bonds at 2850.3 cm and 2946.5 cm. The
peak at 1715.3 and 1684.9 cm could indicate a C-O bond or could indicate the C-C bonds of a
ring. The IR also has a lot of interference in it indicating the ring structure seen in morpholine. It
also has a lot of peaks in the fingerprint region below 1500 cm.