Form the given molecules, we need to find out which compound undergoes Keto-enol tautomers. Concept Introduction: A carbonyl compound that has a-hydrogen on a a-carbon changes its form to enol through resonance. Both the form stays in equilibrium. a-hydrogen is the hydrogen which attached to a a-carbon for a carbonyl compound. a-carbon is carbon adjacent to the carbonyl carbon. If a compound don’t have any a hydrogen is does not undergo Keto-Enol tautomerism.

Question

Nitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Answer 1

Question

Chapter 17, Problem 17.43P

Interpretation Introduction

Interpretation:

Form the given molecules, we need to find out which compound undergoes Keto-enol tautomers.

Concept Introduction:

A carbonyl compound that has a-hydrogen on a a-carbon changes its form to enol through resonance. Both the form stays in equilibrium.

a-hydrogen is the hydrogen which attached to a a-carbon for a carbonyl compound. a-carbon is carbon adjacent to the carbonyl carbon. If a compound don’t have any a hydrogen is does not undergo Keto-Enol tautomerism.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Nitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Sodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Aspirin from Wintergreen: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4. 3. Calculate the exact monoisotopic mass of aspirin showing your work. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?