Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Overview

Synthesis Acid (H2SO4) catalyzed Fischer Esterification reaction of a Carboxylic Acid (Acetic Acid) with the Hydroxyl group of an Alcohol (Isopentyl [amyl] Alcohol). This is a Condensation reaction where the molecules become joined through the intermolecular elimination of water. Refluxing - Reagents will be Refluxed for about 60 minutes.

Liquid/Liquid Extraction - The product will be washed several times with Water, Sodium Bicarbonate, Sodium Chloride. Purification & Boiling Point (Simple Distillation) may be omitted Refractive Index Infrared Spectrum References Pavia Schornick
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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

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The Laboratory Report: Synthesis Experiment Mass, Moles, Molar Ratio, Limiting Reagent, Theoretical Yield Procedures Title Concise: Simple Distillation, Dry Sample, IR Spectrum, etc. Materials & Equipment (2 Columns in list (bullet) form) Note: include all reagents & principal equipment used, including details of distillation setup Description: Use list (bullet) form Concise, but complete description

Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

he Laboratory Report: (Cont) Results Neat, logically designed template to present results Summary experimental results, including Theoretical Yield results, in paragraph form Analysis & Conclusions Limiting reagent Discuss reaction mechanism in the context of your experimental results Verification of product

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Reagents Acetic Acid Mol Wgt Density 0.876 Boiling Point 142oC % Acid 1.4040 Isopentyl (amyl) Alcohol Mol Wgt Density Boiling Point Sulfuric Acid
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Product Isopentyl (amyl) Acetate - 60.05 g/mole Mol Wgt - 130.19 g/mole - 1.049 g/mL Density - 117.9oC Boiling Pnt - 100% Ref. Index -

- 88.15 g/mole - 0.809 g/mL - 130.0oC

Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Heating Under Reflux

The reaction mixture is heated in a reflux apparatus consisting of a 25 or 50 mL round bottom flask attached to a vertical watercooled condenser set in a heating mantle.
Liquid/Liquid Extraction

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Elements of the Experiment

Equilibrium

Reaction equilibrium does not favor formation of the ester Therefore, an excess of one of the reagents (Acetic Acid Cheap!!!) is used to force the equilibrium to product side, i.e., to the right

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Elements of the Experiment (Cont)

Liquid/Liquid Extraction

The reaction mixture is mixed with Distilled Water and placed in a separatory funnel where the phases separate into two layers Aqueous (higher density) layer on bottom and the Organic layer on top. Separate the Aqueous phase into a waste beaker. Extract Organic phase twice with 5% Sodium Bicarbonate to remove excess acid. Discard Aqueous phase into waste beaker. Extract Organic phase twice with Saturated Sodium Chloride to remove excess water. Discard Aqueous phase into waster beaker.
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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Elements of the Experiment (Cont) Dry Product Dry crude ester (organic layer) with Anhydrous Sodium Sulfate (less than 1 gram). Purification Simple Distillation (if so instructed) Mass of Product Percent (%) Yield Refractive Index Infrared (IR) Spectrum

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Procedure

Measure out ~10 mL of Glacial Acetic Acid to the nearest 0.1 mL and compute the mass from the volume and density Weigh the Isopentyl Alcohol in the vial to the nearest 0.001 g Mix the reagents in a Beaker, swirling gently to ensure complete solution If necessary, heat gently to help dissolution of reactants Carefully add 1.0 mL concentrated Sulfuric Acid to the mixture mixing (swirling) quickly
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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

rocedure (Cont)

Set up a Reflux Apparatus using 50 mL round bottom flask. Add a Corundum or Teflon (not calcium carbonate) boiling chip and heat the mixture under Gentle reflux for 50 60 minutes. Cool the mixture to Room Temperature. Liquid/Liquid Extraction

Transfer the mixture to a 125 mL Separatory Funnel using a Short Neck stem funnel Rinse reaction vessel with 10 mL Distilled Water and add to mixture in separatory funnel

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Procedure (Cont)

Liquid/Liquid Extraction (Cont) Mix phases by shaking and venting Remove the lower aqueous layer and put it aside for later disposal Extract the upper organic layer again with 10 mL aqueous Sodium Bicarbonate to remove excess Acid The reaction between the residual acid and Sodium Bicarbonate produces CO2 gas and could be under considerable pressure in the separatory funnel. Hold the stopper firmly and release the stopcock very slowly so the venting of the gas is controlled
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Note:

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

rocedure (Cont)

Liquid/Liquid Extreaction (Cont)

Remove the lower aqueous layer and add to previous waste aqueous solution Repeat the NaHCO3 extraction a second time Perform a third extraction of the upper organic layer in the Separatory Funnel with 10 mL of saturated Sodium Chloride to remove excess water Remove the lower aqueous layer and add to previous waste aqueous solution

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

rocedure (Cont)

Liquid/Liquid Extraction (Cont)

Repeat the Sodium Chloride extraction a second time

Transfer the organic layer containing the crude ester to a small, clean, dry beaker Instructor will add 1.0 g of Anhydrous Sodium Sulfate Note: If mixture does not appear to dry (drying agent will clump), add a little more Sodium Sulfate

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

rocedure (Cont) llow the mixture to settle f so instructed, purify and determine the boiling point of the sample using Simple Distillation (Boiling Point of Isopentyl Acetate is 142oC) re-weigh a small, clean Erlenmeyer flask or the original vial that has been cleaned and dried ecant the sample into the pre-weighed Flask or vial leaving all solid material in the beaker

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Synthesis of Isopentyl (Amyl) Acetate Ester (Banana Oil)

Procedure (Cont) Determine percentage yield Measure the Refractive Index and correct for temperature Obtain the IR Spectrum

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