This document provides instructions for a lab experiment on esterification. Students will synthesize isopentyl acetate from isopentyl alcohol and acetyl chloride. The reaction will be purified using column chromatography over silica gel. Key steps include refluxing the reactants, washing with sodium bicarbonate, separating layers, packing and running the column, and calculating percent yield. The mechanism of esterification using an acid chloride will be drawn and questions about the reaction conditions, products, and relationship between TLC and column chromatography will be answered in the post-lab.
This document provides instructions for a lab experiment on esterification. Students will synthesize isopentyl acetate from isopentyl alcohol and acetyl chloride. The reaction will be purified using column chromatography over silica gel. Key steps include refluxing the reactants, washing with sodium bicarbonate, separating layers, packing and running the column, and calculating percent yield. The mechanism of esterification using an acid chloride will be drawn and questions about the reaction conditions, products, and relationship between TLC and column chromatography will be answered in the post-lab.
This document provides instructions for a lab experiment on esterification. Students will synthesize isopentyl acetate from isopentyl alcohol and acetyl chloride. The reaction will be purified using column chromatography over silica gel. Key steps include refluxing the reactants, washing with sodium bicarbonate, separating layers, packing and running the column, and calculating percent yield. The mechanism of esterification using an acid chloride will be drawn and questions about the reaction conditions, products, and relationship between TLC and column chromatography will be answered in the post-lab.
This document provides instructions for a lab experiment on esterification. Students will synthesize isopentyl acetate from isopentyl alcohol and acetyl chloride. The reaction will be purified using column chromatography over silica gel. Key steps include refluxing the reactants, washing with sodium bicarbonate, separating layers, packing and running the column, and calculating percent yield. The mechanism of esterification using an acid chloride will be drawn and questions about the reaction conditions, products, and relationship between TLC and column chromatography will be answered in the post-lab.
Complete the pre-lab cover page and develop a procedure. Draw the mechanism of the reaction you will complete in lab. Use the proper arrow drawing convention to show all bond making and bond breaking steps in the reaction. Include all intermediates.
Learning Goals: Understand the mechanism of esterification and how it relates to ester hydrolysis. Understand how column chromatography can be used to separate compounds of different polarity. Relate column chromatography to TLC separation
Introduction:
Esters are common in nature,
they are formed from a condensation reaction between an alcohol and a carboxylic acid derivative. They consist of a carbonyl carbon bound to an alkoxy group. Esters give flowers their pleasant aromas and fruits their tastes. Most flavors and aromas consist of a mixture of many different esters however; one ester that predominates. The difference of the smells and tastes are derived from how they fit in your taste and olfactory receptors. Slight changes in the chemical structure of an ester can result in dramatically differing tastes, because of this esters are used as flavorings in food and beverages. Examples of this can be found in pineapples and apples, pineapples gain their taste and smell from ethyl butyrate whereas apples gain their smell and taste from methyl butyrate (see Figure 1). Despite the pleasant nature of esters, they are seldom used in products applied to skin. The low pH of skin combined with body heat facilitate hydrolysis of esters in to carboxylic acids with small carbon chains and alcohols that smell vinegar and rancid milk, thus defeating the purpose of application. In this lab you will synthesize isopentyl acetate using isopentyl alcohol and acetyl chloride to make isopentyl acetate.
For humans, isopentyl acetate has a characteristic smell that is associated with bananas (thus isopentyl acetate is nicknamed banana oil).
Lab setup: Isopentyl acetate is a component of honeybee alarm pheromones. Pheromones are compounds that when released affect the behavior of members of the same species. If this compound is spilled on an item, it can cause bees to attack the item. If you spill it on you wash your hands and flush with water for ten minutes. Procedure: 1.) Obtain a hot plate and an aluminum block from the stock room. CaCl2 2.) Prepare a drying tube by inserting a piece of cotton up to the bend of the tube using a spatula. Next fill the tube with ~1 cm of calcium chloride (CaCl2) and plug with cotton as shown in Figure 2. 3.) Obtain a 5 ml conical vial with a spin vane. 4.) Add to the vial 200 l of isopentyl alcohol Cotton Plug and 800 l of acetyl chloride. 5.) Place the vial in the largest hole in the aluminum block and clamp to a ring stand in your hood with a three-fingered clamp. Figure 2: proper setup of a drying tube. 6.) Attach to the top of the vial a reflux condenser with a drying tube and secure to the ring stand in your hood. 7.) Stir reaction mixture for 15 minutes at room temperature with water flowing through the condenser. 8.) Carefully disassemble you condenser and use a forceps to remove the spin vane from your reaction mixture. 9.) Slowly add ~1 ml of a 5% sodium bicarbonate solution via Pasteur pipette. 10.) Cap the vial and gently mix the vial and let the layers separate. 11.) Using a Pasteur pipette carefully remove the bottom layer with a Pasteur pipette and discard in the waste container. 12.) Repeat steps 9 11 three additional times. 13.) Prepare a silica gel column by packing a small piece of cotton down a 5 Pasteur pipette using the tip of a 9 Pasteur pipette (see Figure 3.). 14.) Once the cotton plug is in place add ~3 cm of silica gel to the Pasteur pipette make sure to tap the pipette gently against the bench top to pack it down uniformly. a. Caution silica gel can aerosolize and irritate your lungs if you breathe it in. 15.) After packing down the silica gel bed, carefully overlay ~2 cm of sodium sulfate (Na2SO4) to the pipette. 16.) Clamp your pipette to the ring stand in your hood. 17.) Prepare a vial with a boiling stone in it 18.) Determine the mass of the vial and boiling stone and record in the data section of your lab report. 19.) Place the reweighed vial from step 18 underneath the tip of the Pasteur pipette. 20.) Before adding your reaction mixture from step 12, add ~2-3 mL of methylene chloride to your pipette to wet the silica gel completely. a. This is step is crucial in separation. 21.) Once the column is wet add your reaction mixture to the pipette. 22.) Rinse the crude reaction vial with ~0.5mL of methylene chloride and add to the Pasteur pipette. 23.) Let the solvent drain through the pipette until it reaches the top of the sodium sulfate bed, then add ~1mL of methylene chloride to the pipette and let drain down to the sodium sulfate layer. 24.) Next carefully boil off the solvent from the pre-weighed vial by heating to 75 oC. 25.) Once the vial has reached a constant mass, i.e. all the solvent is gone, calculate your percent yield and record in the data section of your lab report. 26.) Allow your hot plate to cool to room temperature and return it to the stockroom. Post Lab: Include what is required in the Lab Expectations handout. Calculate percent yield for your reaction (this will require you to determine which reactant is limiting).
Answer the following questions as the last part of your lab report.
1. Draw the mechanism of an esterification using an acid chloride and alcohol.
2. Could acetic acid be used in the esterification, instead of acetyl chloride? Why or why not? 3. Could acetic anhydride be used? 4. Instead of getting your desired product, what would happen if your glassware was wet before you started the reaction? 5. What is the relationship between TLC and Column Chromatography? 6. What is the limiting reagent in the reaction that you ran? Prove your answer with limiting reagent calculations in the calculation section of the post-lab.
