Vetaka Prajakchaikul (Ting-Ting)

1108 ID: 5761172

Semester 1 Final
Chemistry 11
This final will teach you to do some research and use the material we have learnt thus far.
Things such as mole calculations and % yields.
Your task is to find an academic paper (only academic papers are allowed) for some kind of
compound, any compound. I recommend finding a compound of something youd potentially
actually like to make.
For example, perhaps you wish to start a cosmetic line. Cosmetics contain a number of
different compounds mixed in. Maybe you wish to find out how to make something like
glycerin or sodium dodecyl sulfate.
It will be shown in class how to find academic papers.
Once you have found your paper you need to answer the following questions:
1. What is the purpose of your compound? How is it useful?
- Eugenol, essential oil, the aromatic compound obstructed from botanical material
such as tree bark, flowers, steam, leaves, needles, plant and roots. It is used in the
production of perfume, cosmetic, air freshener and household cleaning products as an
ingredient.
2. What is the starting material to make your product?
- Hydroxide (HNaO) 0.48 g, 0.012 mole
1 mole C 17 H 16 O 3
0.012 mole HNaO
= 0.12 mole C17H16O3
1 mole HNaO
-

Eugenol (C10H12O2)1.64 g, 0.010 mole

1 mole C 17 H 16 O 3
0.010 mole C10H12O2 2 mole C 10 H 12O 2
3a (RCOCI) 0.010 mole
1 mole C 17 H 16 O 3
0.010 mole RCOCI 1 mole RCOCI

= 0.005 mole C17H16O3

= 0.010 mole C17H16O3

C17H16O3 = (C 17) + (H 16) + (O 3) grams

C17H16O3 = (12.011 17) + (1.008 16) + (15.999 3) grams
C17H16O3 = 268.312 grams
0.005 (C17H16O3) mole
268.312 grams C 17 H 16O 3
0.005 mole C17H16O3
= 1.34156 mole C17H16O3
1 mole C 17 H 16 O3

Eugenol (C10H12O2) is limiting reagent (0.005 mole C17H16O3), it is the starting

material of the product.
3. What is the % yield given in the paper?
- 87% 4a (C17H16O3)
4. How many grams of product were made?
C17H16O3 = (C 17) + (H 16) + (O 3) grams

Vetaka Prajakchaikul (Ting-Ting)

1108 ID: 5761172
C17H16O3 = (12.011 17) + (1.008 16) + (15.999 3) grams
C17H16O3 = 268.312 grams
263.312 grams C 17 H 16O 3
0.005 mole C17H16O3
= 1.34156 grams
1 mole C 17 H 16 O3
C17H16O3
Theoretical yield = 1.34156 grams C17H16O3
actual yield
100
% yield = theoritical yield
actual yield
87 % = ( 1.31656 grams C 17 H 16 O 3 ) 100%
-

Actual yield = 1.1454 grams C17H16O3

5. How many moles of product were made?

Theoretical yield = 1.34156 grams C17H16O3
1 mole C 17 H 16 O3
1.34156 g C17H16O3 268.312 grams C 17 H 16O 3
-

= 0.005 mole C17H16O3

0.005 mole C17H16O3

6. How many grams of product would be produced if they obtained a 95% yield?
Theoretical yield = 1.34156 grams C17H16O3
actual yield
100
% yield = theoritical yield
actual yield
95 % = ( 1.34156 grams C 17 H 16 O 3 ) 100%
- Actual yield = 1.2745 grams C17H16O3
7. If they started with 5 grams of starting material, how much product could they have
theoretically made?
C10H12O2 = (C 10) + (H 12) + (O 2) grams
C10H12O2 = (12.011 10) + (1.008 12) + (15.999 2) grams
C10H12O2 = 164.204 grams
C17H16O3 = (C 17) + (H 16) + (O 3) grams
C17H16O3 = (12.011 17) + (1.008 16) + (15.999 3) grams
C17H16O3 = 268.312 grams
1 mole C 10 H 12O 2
1 mole C 17 H 16 O 3

5 grams C10H12O2
164.204 grams C 10 H 12O 2
2 mole C 10 H 12O 2

268.312 grams C 17 H 16O 3

1 mole C 17 H 16 O3

- Theoretical yield = 4.085 grams C17H16O3

8. If we needed to make 10 grams of product, how much starting material would we
need to use?

Vetaka Prajakchaikul (Ting-Ting)

1108 ID: 5761172
10 g C17H16O3

1mole C 17 H 16 O 3
268.312 g C 17 H 16 P 3

2 mole C 10 H 12 O2
1 mole C 17 H 16 P 3

164.204 g C 10 H 12 O2
1mole C 10 H 12 O2

Staring material = 12.24 grams C10H12O2

You must attach your answers and the academic paper when handing in.

Chemistry Project
Eugenol synthesis
Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a
member of the phenylpropanoids class of chemical compounds. It is a colorless
to pale yellow oily liquid extracted from certain essential oils especially
from clove oil, nutmeg,cinnamon, basil and bay leaf. It is present in
concentrations of 8090% in clove bud oil and at 8288% in clove leaf oil.

Vetaka Prajakchaikul (Ting-Ting)

1108 ID: 5761172

PubChem CID:

3314

Chemical Names:

Eugenol; 4-Allylguaiacol; 4-Allyl-2-methoxyphenol; Eugenic acid; Allylguaiacol; C

Molecular Formula:

C10H12O2

Molecular Weight:

164.20108 g/mol

InChI Key:

RRAFCDWBNXTKKO-UHFFFAOYSA-N

UNII:

3T8H1794QW

Modify Date:

2016-01-10

Create Date:

2004-09-16

Sodium hydroxide
Sodium hydroxide is a white crystalline odorless solid that absorbs moisture
from the air. It is a manufactured substance. When dissolved in water or
neutralized with acid it liberates substantial heat, which may be sufficient to
ignite combustible materials. Sodium hydroxide is very corrosive. It is generally
used as a solid or a 50% solution. Other common names include caustic soda
and lye.

Vetaka Prajakchaikul (Ting-Ting)

1108 ID: 5761172

PubChem CID:

14798

Chemical Names:

SODIUM HYDROXIDE; Caustic soda; 1310-73-2; Sodium hydrate; So

Molecular Formula:

HNaO

Molecular Weight:

39.997109 g/mol

InChI Key:

HEMHJVSKTPXQMS-UHFFFAOYSA-M

UNII:

55X04QC32I

Safety Summary:

Laboratory Chemical Safety Summary (LCSS)

Modify Date:

2016-01-10

Create Date:

2005-03-26

SODIUM HYDROXIDE is a highly caustic substance that is used to neutralize acids and make
sodium salts. (From Merck Index, 11th ed)

Vetaka Prajakchaikul (Ting-Ting)

1108 ID: 5761172
To a stirred solution of sodium hydroxide (0.48 g, 12 mmol) and eugenol
(1.64 g, 10 mmol) in water (10 mL) were added acid chlorides 3a and 3e
q (10 mmol) dropwise at room temperature. After 30-min stirring at room
temperature the mixture was extracted with dichloromethane
(2 15 mL), washed with 5% sodium carbonate (2 15 mL), dried with
anhydrous sodium sulfate, and concentrated under reduced pressure to
provide the desired compounds. All products were crystallized from
ethanol except 4h and 4k which were purified by column
chromatography (silica gel 60; 230400, eluent: chloroform).
6.3.1. 4-Allyl-2-methoxyphenyl benzoate (4a)
White crystal. Yield: 87%; mp 5556 C. IR: 1727 cm1 (C O). 1H NMR
(CDCl3): 3.45 (d, 2, J = 6.6 Hz, CH2), 3.80 (s, 3, OCH3), 5.015.25 (m, 2,
H2C ), 5.806.25 (m, 1, CH), 6.82 (d, 1, J = 8.4, H-5), 6.85 (s, 1, H-3), 7.10
(d, J = 8.4, H-6), 7.407.72 (m, 3, H-3, H-4, H-5), 8.22 (d, 2, J = 7.9, H-2, H6). Found C, 76.21; H, 6.03. C17H16O3 requires: C, 76.10; H, 6.01%.
Source:
http://www.sciencedirect.com/science/article/pii/S0968089607008826
https://pubchem.ncbi.nlm.nih.gov/compound/eugenol
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_hydroxide