Solution Found!
One of the constitutional isomers of xylene was treated
Chapter 18, Problem 18.5(choose chapter or problem)
One of the constitutional isomers of xylene was treated with sodium, methanol, and ammonia to yield a product that exhibited five signals in its 13C NMR spectrum. Identify which constitutional isomer of xylene was used as the starting material.
Questions & Answers
QUESTION:
One of the constitutional isomers of xylene was treated with sodium, methanol, and ammonia to yield a product that exhibited five signals in its 13C NMR spectrum. Identify which constitutional isomer of xylene was used as the starting material.
ANSWER:Step 1 of 3
When we consider the Birch reduction of the three possible isomers of xylene, we place the 1,4-diene bonds such that they are substituted with as many methyl groups as possible. These are the most stable products and therefore the major products of the reactions.
Starting with ortho-xylene, we see that the Birch reduction product would have four signals in its \({ }^{13} \mathrm{C}\) NMR spectrum: the methyl groups, the quaternary carbons, the methylene carbons, and the non-substituted alkene carbons.
