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Spectroscopic identification of organic compounds: Question 20

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Identify Compound T and explain how the data from each of (a) to (d) provides the information to support your
answer.

(a) Elemental analysis of Compound T

(b) Mass spectrum of Compound T

(c) Infrared spectrum of Compound T

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(d) 1H NMR data for Compound T

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(a) From the elemental analysis the empirical formula of Compound T is CH2.

(b) The M+ peak at m/z = 70 gives a mass equal to five times that of the empirical mass so the molecular formula of
Compound T is C5H10. The peak with the m/z value of 55 suggests loss of a methyl group to give the C4H7+ fragment.  Loss
of an ethyl group (M – C2H5)+, i.e. C3H5+ is likely to have produced the peak at m/z = 41.

(c) The strong sharp absorptions at just below 3000 cm-1 show the presence of the C–H bonds. The sharp absorption at 1651
cm-1 suggests a C=C double bond so Compound T is an alkene.

(d) The 1H NMR spectrum shows that the ten hydrogen atoms are in four different chemical environments in the ratio 2:2:3:3.
The singlet at 4.6 ppm has the chemical shift due to –C=CH2– which suggest the double bond is on the first carbon atom
which is bonded to two hydrogen atoms with no H atoms on the adjacent carbon atom. The singlet at 1.6 ppm suggests a
methyl group attached to a carbon atom containing no hydrogen atoms bonded to it. The quartet and triplet at 2.0 ppm and 1.0
ppm respectively are indicative of an ethyl group attached to the other carbon atom of the double bond.

All this information taken together confirms that Compound T is 2-methylbut-1-ene, H2C=C(CH3)C2H5.

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