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Lab Report 9 - synthesis of banana oil

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36 views3 pages

Lab Report 9 - synthesis of banana oil

Uploaded by

Kylie
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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10 points

Lab Report 9: Synthesis of Isopentyl Acetate (Banana Oil)

Your Name: Jack Mladic Lab Partner: Danie Lodin Section: 3

All pages must be stapled together, with this being the top page.

Part 1: Experimental Data and Results (include appropriate unit) (2 pt)

1. Draw a balanced reaction equation showing the conversion of acetic acid and isopentyl
alcohol to banana oil. Then fill out the table below.

Acetic acid Isopentyl alcohol

Mass used in lab 5.0 g 4.0 g


M.W. 60.052 g/mol 130.18 g/mol
Moles .08326 moles .03072 moles
2.

Theoretical yield of banana oil 5.0g acetic acid/(60.052g/mol) = 0.08326 mol acetic acid
(show your calculation) which would give 0.08326 mol of isopentyl alcohol
0.08326 mol of isopentyl alcohol * 130.18g/mol = 10.839
g of banana oil
Actual yield 3.02g
% yield Actual/theoretical = 3.02/10.839= 0.2786 = 28%

Part 2: Spectral Analysis of the product

2. (1pt) Carefully examine your IR spectrum for the product and compare it to the standard in
the SDBS database (attached both yours and standard’s). Did your IR indicate that all
isopentyl alcohol had completely reacted? Why?

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10 points

We can tell that all of the isopentyl alcohol reacted due to a lack of an OH bond in our products
IR spectrum (isopentyl alcohol has an OH bond). If there was an OH bond we would see a
broad peak at around 3000 cm-1.

3. (1pt) Banana oil (isopentyl acetate) contains a C=O which should show up in its IR
spectrum. However, the reactant acetic acid also contains a C=O bond. In the space below,
draw the structures of both molecules. How would you confirm that in your product IR
spectrum the peak near 1700 cm-1 is due to isopentyl acetate but not acetic acid?

We can confirm that our products IR spec peak near 1700 cm-1 is due to isopentyl acetate but
not acetic acid due to the different functional groups. Acetic acid’s functional group is carboxylic
acid, which this peak is from 1725-1700 cm-1. Isopentyl acetate’s functional group is an ester
which this peak is from 1750-1730 cm-1. When we look at our products peak we see that the
1700 peak is at 1739.4 cm-1. This would fit into the ester functional group proving that this peak
is not due to acetic acid.

4. (3 pt) HNMR of banana oil is shown below. Draw the structure of banana oil in the space
below, sprout out all H’s and label different H’s as a, b, c… Briefly explain the splitting
pattern of all the H signals (triplet, singlet, ….).

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10 points

Part 3: Reaction mechanism

(2pt) Complete the arrow pushing for the synthesis of banana oil. Follow the isotope labeled O 18
throughout this mechanism by labeling the correct oxygen in each step with a superscript O18.

(1pt) Does O18 ends up in banana oil or in water?


O18 ends up in water

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