1) Draw the resonance forms of the protonated carboxylic acid in the beginning of the Fisher Esterification mechanism. 2) What would happen if the product mixture was washed with aqueous sodium bicarbonate before being washed with water? Could the product still be isolated? Explain your answer. 3) Draw the alcohol and carboxylic acid needed to synthesize the ester below. Place an arrow next to the oxygen in the carboxylic acid or alcohol that corresponds to the oxygen indicated by the arrow in the ester below. 4) Given the following reagents, dichloromethane, water, acetone, \( 10 \% \) aqueous \( \mathrm{HCl}, 10 \% \) aqueous \( \mathrm{NaHCO}_{3} \) and anhydrous sodium sulfate, devise a method to separate 4 -methylphenyl acetate from the rest of the reaction mixture for the reaction below. (S)
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- Start with the carboxylic acid group (RCOOH). - Protonate the carbonyl oxygen to form RCOOH₂⁺. - Draw the resonance structures: 1. The positive charge is on the carbonyl oxygen. 2. The positive charge is on the hydroxyl oxygen after shifting the double bond. Show more…
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3) You will utilize extraction to help purify your ester compound. Explain where your starting materials, catalyst, and products will partition (into the aqueous or organic). What would the difference be if you used deionized water instead of what is called for in the lab? 4) On industrial scale, the liquid products of this reaction are typically isolated by distillation. Contrast the Greenness (citing the relevant 12 Principles of Green Chemistry) of distillation of high boiling esters versus purification by extraction.
Snehal J.
1. The esterification reaction performed is an equilibrium reaction. Referring to the experimental procedure and laboratory data, identify the methods employed to drive the formation of product (ie. to shift the equilibrium position to the right). 2. In this experiment, the prepared ester is separated by extraction. In a typical organic extraction, the reaction mixture is treated with both an organic solvent and water to form two distinct layers. However, in this experiment, the reaction mixture is treated only with water. Explain then, how an organic layer is formed? 3. Following the initial extraction, the organic layer is treated with sodium bicarbonate (NaHCO3) solution, upon which effervescence is observed. Briefly explain why this is performed, and account for the formation of the effervescence. 4. The isoamyl acetate is isolated from this synthesis (quite) pure. Other than H1NMR, suggest a simplest method by which the purity of the isolated material can be assessed.
Aarya B.
Smell Your Product - Preparing Scented Esters Via Fischer Esterification A. (2 pts.) Identify the starting material to prepare the internal ester (lactone) shown below. B. (4 pts.) Draw the first intermediate and the final product for the reaction below. C. (4 pts.) In the Fischer esterification shown below, where will the isotopically labeled oxygen (O*) end up, in the ester or the water? Draw detailed structures.
Sri K.
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