2. Below are two other organic dyes that both produce a yellow color when dissolved. Which of the solvents used in this experiment (select one solvent for each dye) could be used to dissolve samples of each of these dyes (individual samples, not a mixture)? HN- Radiant Yellow Alizarine Yellow OH Na

C. The NMR spectrum shown below represents the product (ethyl 4-aminobenzoate) after it has been shaken with deuterium oxide (D₂O). Write the equation for the reaction which occurs when D₂O reacts with ethyl 4-aminobenzoate. Draw the structure of the compound next to the spectrum and label the protons so that they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table. D. on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly. B' A 10 ppm EQUATION: 5 ppm E υ C' STRUCTURE: Proton label Chemical shift | Relative integration Multiplicity (ppm) A' B' C' 0 ppm E' Comment on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly.

3. 'H-NMR interpretation When dissolved in CDC13, phenacetin shows 6 signals. All of the peaks are sharp, except for the signal f not below. Draw the chemical structure of phenacetin, labeling each hydrogen with an alphabetical letter. Make a larger version of the chart below (half or full page), and complete it with the missing information. Explanation of splitting patter 8 (ppm) Letter # H (integration Splitting pattern value) 7.94 f 1 Broad singlet 7.36 e 6.80 d 3.98 с 2.09 b 1.38 a Extra Credit Question 4. Describe/predict how the 'H-NMR spectrum differs for acetaminophen.

Suppose that the two pigments in two samples contain red pigment and that the red pigment in sample A is more soluble in acetone than the red pigment in sample B. Form a hypothesis regarding which red pigment has a higher Rf value, explain your answer.