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Selecting a Spectroscopic Tool II

If you needed to distinguish each of the compounds in the following pairs ( A & B ) from each other, which spectroscopic method: infrared (IR), mass spectrometry (MS), 1H nmr (NMR) or ultraviolet-visible (UV) would be best suited for this purpose? Assume that you do not have a reference sample of either compound for direct comparison.

Compound A
Compound B
IR
MS
NMR
UV
Skeletal structure of DABCO, 1,4-diazabicyclo[2.2.2]octane, a bicyclic diamine cage Skeletal structure of 1,4-cyclohexanedione, a six-membered ring with two C=O groups para

Skeletal structure of 1,2,2-trichloropropane, CH3CCl2CH2Cl 		Skeletal structure of 1,1,2-trichloropropane, CH3CHClCHCl2

Skeletal structure of 1,4-cyclohexadiene, a ring with two unconjugated double bonds 		Skeletal structure of 1,3-cyclohexadiene, a ring with two conjugated double bonds

Skeletal structure of 1,4-dioxane, a six-membered ring with two oxygens para 		Skeletal structure of 12-crown-4, a macrocyclic ring with four ether oxygens

(CH3)2CHCH2-OH
(CH3)3C-OH

C2H5-Cl
C2H5-Br
Skeletal structure of 4-(dimethylamino)benzoyl chloride Skeletal structure of 4-chloro-N,N-dimethylbenzamide




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