Compound A, C8H11NO, smells as if it might have been isolated from an extract of dirty
Chapter 26, Problem 26.4(choose chapter or problem)
Compound A, C8H11NO, smells as if it might have been isolated from an extract of dirty socks. This compound can be resolved into enantiomers and it dissolves in 5% aqueous HCl. Oxidation of A with concentrated HNO3 and heat gives nicotinic acid (3-pyridinecarboxylic acid; see Eq. 26.26.) When A reacts with CrO3 in pyridine, compound B (C8H9NO) is obtained. Compound B, when treated with dilute NaOD in D2O, incorporates five deuterium atoms per molecule. Identify A, and explain your reasoning
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