What would be the product you would expect from your carbonyl compound reacting

Question

What would be the product you would expect from your carbonyl compound reacting with aniline in place of the 2, 4-DNP? If ethyl amine (CH_3CH_2NH_2) used in place of 2, 4-DNP would there be any difference in the color of the compound formed? What would you predict for the color of this compound? Provide a sketch of what you would expect for the^1 H NMR of your product. In addition indicate how many^13 C resonances you would expect for this compound. Which solvent do you think would be best for the DNP reaction that you ran in this experiment: water, 50% water-ethanol, or pure ethanol? Explain your reasoning in terms of the fact that this is an equilibrium reaction. The reaction of carbonyl compounds with hydrazine (NH_2-NH_2) also give the expected hydrazine products when hydrazine is present in excess. However if the mole ratio of hydrazine is 1:1 then a different product called an azine starts to form in appreciable amounts. Draw the expected structure for the hydrazine that would be expected from your carbonyl compound with excess hydrazine. Provide a likely structure for the azine product that would be expected if the hydrazine is not present in excess. If you isolated a single product (as determined by TLC) could NMR or IR tell if it was the hydrazone or azine? 1 low could you tell the difference between these two compounds using either NMR or IR or both?

Explanation / Answer

1. There will be formation of phenyl imine when aniline reacts with carbonyl agroup. In your case product would be butan-2-phenylimine.

2. Product would be ethyl-1-phenylamine.

4. Preferred solvent is water as it gives more H3O+ ions as compared to ethanol (ethanol has high pH as compared to water).

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