Adriana English
SEC 5: SARA
CHM 2211L
Pre-Lab 15
Title: Nitration of Methyl Benzoate
References: S. Profeta Jr.; CHM2211l Lab Manual, p.187-190, Chemspider.com; pubchem.com
Purpose: To perform an electrophilic aromatic substitution reaction on methyl benzoate and use TLC
analysis to analyze the product.
Molecule Methyl Benzoate Sulfuric Acid Nitric Acid Methanol Hexane
Name and
Structure
MW (g/mol) 136.15 98.08 63.01 32.04 86.18
grams 1.2 1.84 1.56 0.79 --
moles 0.0088 0.019 0.025 0.025 --
MP (deg C) -12 10 -42 -98 -95
BP (deg C) 198-199 -290 120.5 65.4 68-69
FP (deg C) 83 11 120.5 11 --
Density 1.088 1.840 1.41 0.791 0.7
(g/mL)
Aqueous <0.1 Miscible >100 miscible 0.0095
solubility(g/L
)
Handling Wear gloves, don’t Wear gloves, Don’t Wear Avoid contact w/ Avoid contact w/
inhale/ingest, very inhale/ingest, avoid gloves/goggles, eyes/skin, don’t eyes/skin, don’t
flammable skin/eyes. Don’t use avoid skin/eyes, inhale, wear gloves inhale/ingest
w metal burns
Toxicity irritates skin/eyes, Irritation skin and Skin, eye, lung Irritation of skin, Irritates skin and eyes
respiratory/digestive eyes, burns irritation, lung and eyes, lungs and
tract respiratory/digestive eye damage respiratory tract
system issues
Molecule Ethyl Acetate Water Methyl 2 -nitro Methyl 3 -nitro Methyl 4 -nitro
Name and Benzoate (ORTHO) Benzoate (META) Benzoate (PARA)
Structure
MW (g/mol) 88.11 18.02 181.15 181.15 181.15
grams -- -- --- 1.597 (theoretical) ---
moles -- -- -- 0.0088 (theoretical) ---
MP (deg C) -83 0 -13 78-80 95
BP (deg C) 77 100 275 279 94-96
Density 0.9 1 n/a 1.283 ----
(g/mL)
Aqueous 83 soluble --- Insoluble ---
solubility(g/L
)
Handling Wear gloves, don’t none Wear Avoid contact w/ Avoid contact w/
inhale/ingest, gloves/goggles, eyes/skin, don’t inhale eyes/skin, don’t
goggles avoid skin/eyes, inhale/ingest
don’t inhale/ingest
Toxicity Severe skin burns , none Skin, eye, lung Irritation of skin, eyes, Irritates skin and eyes
irritates skin/eyes irritation lungs
- The meta product has mp of 78 deg C
- The ortho product has a mp of -13 deg C
- The Para product has mp of 94 deg C
Theoretical Yield:
Limiting Reagent: 0.0088 moles 0.0088 moles product
0.0088 x(181.15/ 1 mole) = 1.597 OR
1.2 methyl benzoate x (1 mol Methyl Benzoate / 136.15g) x ( 1 mol Methyl 2 -nitro Benzoate / 1 mol Methyl Benzoate) x 181.15g/ 1 mol methyl 2-nito benzoate
= 1.6g
Procedure:
1. Prepare a cool water bath in a 100 mL beaker for emergency use.
2. Add 1 mL sulfuric acid dropwise to nitric acid, combine them into a 20mL vial.
3. Mix the solution and let it sit at room temperature.
4. Check with a glass thermometer to make sure it is between room temperature and about 40C.
5. Place 1.2g of methyl benzoate in a separate 20mL vial.
6. Use 1 mL syringe to slowly transfer the previous H2SO4/HNO3 solution dropwise to the ester
7. Keep the temperature between 20-40C, stirring the solution, adding for about 15 mins.
8. Stir when complete, so the rxn occurs.
9. Place 15g-20g of ice in a 50mL beaker and pour the reaction mixture onto the ice.
10. Allow ice to melt, mixing the solution.
11. Use vacuum filtration to collect the raw product.
12. Leave the solid on the funnel to dry for 15 mins.
13. Recrystallize product from CH3OH 1ml per 1 g of solid.
14. Heat the product gently and collect it with vacuum filtration.
15. Obtain the yield and melting point.
16. Run NMR on the sample.
17. Run TLC trials for all samples.
APPARATUS:
IN-LAB OBSERVATIONS: EXP 15 Adriana English
Procedure:
1. Prepare a cool water bath in a 100 mL
beaker for emergency use.
2. Add 1 mL sulfuric acid dropwise to nitric
acid, combine them into a 20mL vial.
3. Mix the solution and let it sit at room
temperature.
4. Check with a glass thermometer to make
sure it is between room temperature and
about 40C.
5. Place 1.2g of methyl benzoate in a separate
20mL vial.
6. Use 1 mL syringe to slowly transfer the
previous H2SO4/HNO3 solution dropwise
to the ester
7. Keep the temperature between 20-40C,
stirring the solution, adding for about 15
mins.
8. Stir when complete, so the rxn occurs.
9. Place 15g-20g of ice in a 50mL beaker and
pour the reaction mixture onto the ice.
10. Allow ice to melt, mixing the solution.
11. Use vacuum filtration to collect the raw
product.
12. Leave the solid on the funnel to dry for 15
mins.
13. Recrystallize product from CH3OH 1ml per
1 g of solid.
14. Heat the product gently and collect it with
vacuum filtration.
15. Obtain the yield and melting point.
16. Run NMR on the sample.
17. Run TLC trials for all samples.
