Chemistry and Molecular Ion Peak

Megan Adkins-Blanch
11/10/14
TA: David Stephens
CHE 3652-003
Aldol Condensation: 4-methoxychalcone
Abstract: To synthesize 4-methyoxychalcone.
Reaction Mechanism:

Table:
Compound
Molecular Weight (g/mol)
Density (g/mL)
Boiling Point (°C)
Melting Point (°C)
Amount used (g, mL, etc.)
Acetophenone
120.16
1.03
201.7
19.7
1 ml
95% ethanol
46.07
0.8
79
-114

50% NaOH
40.2
1.53
140
12

Anisaldehyde
136.16
1.12
248
-1
1 ml

Structures:
Acetophenone: 95% ethanol: 50% NaOH: Anisaldehyde:

MSDS:
Acetophenone: Very hazardous in case of eye contact (irritant). Hazardous in case of skin contact (irritant). Slightly hazardous in case of ingestion, of inhalation.
95% ethanol: Hazardous in case of skin contact (irritant), of eye contact (irritant), . Slightly hazardous in case of skin contact (permeator), of ingestion. Non-corrosive for skin. Non-corrosive to the eyes. Non-corrosive for lungs.
50% NaOH: Very hazardous in case of skin contact (corrosive, irritant, permeator), of eye contact (irritant, corrosive), of ingestion, . Slightly hazardous in case of inhalation (lung sensitizer).
Anisaldehyde: Very hazardous in case of ingestion. Hazardous in case of skin contact (irritant), of eye contact (irritant), of inhalation.

Procedure:
1. Prepare a 50% NaOH solution by dissolving 1.0 g NaOH in 1 mL of water.
2. You may need to heat the solution to dissolve all the NaOH.
a. The solution mus be cool before it is added to the reaction mixture.
3. Add 1 mL of acetophenone and 1 mL of anisaldehyde to a test tube
4. Add 3 mL of 95% ethanol and stir intil dissolved
5. Add 5 drops of the NaOH solution
6. Stir for 20 min
7. Add to an ice bath until crystallization occurs
8. Filter the crude product
9. Recrystallize with 2 mL of EtOH
10. Filter pure product and collect MP and mass
11. Perform a saturation test with a bromine and potassium permanganate solution
12. Obtain NMR from instructor and identify peaks

Apparatus:

Post Lab:

Observations: