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Selecting a Spectroscopic Tool I

If you needed to distinguish each of the compounds in the following pairs ( A & B ) from each other, which spectroscopic method (infrared or 1H nmr would be best (most certain)? Assume that you do not have a reference sample of either compound for direct comparison.

Compound A
Compound B
IR
NMR
Skeletal structure of 2,3-dimethyl-2-butene, a tetrasubstituted symmetric alkene Skeletal structure of biacetyl (2,3-butanedione), two adjacent C=O groups each bearing a methyl
Cage structure of DABCO, 1,4-diazabicyclo[2.2.2]octane bicyclic diamine

Skeletal structure of succinonitrile, N#C-CH2-CH2-C#N

Skeletal structure of 1,3-propanediol, HO-CH2CH2CH2-OH 		Skeletal structure of 1,3-dioxane, a six-membered ring with two oxygen atoms
Skeletal structure of 4-methoxybenzyl chloride, benzene with CH2Cl and para OCH3 Skeletal structure of 4-chlorophenetole, benzene with Cl and para ethoxy (OCH2CH3)

Skeletal structure of 1,4-dichlorobenzene, benzene with two para chlorines 		Skeletal structure of maleic anhydride, a five-membered cyclic anhydride with C=C




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