Problem: If you did not know the regioselectivity leading to the major product in the Birch reduction of toluene, but you did know that a 1,4-cyclohexadiene is formed, the structural formulas of the two possible major products are given to the right. To learn which one is indeed the major product, one could record the proton-decoupled 13C NMR spectrum of the isolated major product of the reaction. Clearly and concisely describe how you can learn from a quick, and not very involved analysis, of the proton-decoupled 13C NMR spectrum whether the major product is 1-methyl-1,4-cyclohexadiene or 3-methyl-1,4-cyclohexadiene. Most obviously, how would the proton-decoupled 13C NMR spectrum of 1-methyl-1,4-cyclohexadiene differ from the proton-decoupled 13C NMR spectrum of 3-methyl-1,4- cyclohexadiene?

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If you did not know the regioselectivity leading to the major product in the Birch reduction of toluene, but you did know that a 1,4-cyclohexadiene is formed, the structural formulas of the two possible major products are given to the right. To learn which one is indeed the major product, one could record the proton-decoupled 13C NMR spectrum of the isolated major product of the reaction. Clearly and concisely describe how you can learn from a quick, and not very involved analysis, of the proton-decoupled 13C NMR spectrum whether the major product is 1-methyl-1,4-cyclohexadiene or 3-methyl-1,4-cyclohexadiene. Most obviously, how would the proton-decoupled 13C NMR spectrum of 1-methyl-1,4-cyclohexadiene differ from the proton-decoupled 13C NMR spectrum of 3-methyl-1,4- cyclohexadiene?

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