FACULTY OF APPLIED SCIENCES

LABORATORY REPORT CHM 624

ADVANCED ORGANIC CHEMISTRY

EXPERIMENT 1

TITLE: PREPARATION OF 4-VINYLBENZOIC ACID BY A WITTIG REACTION IN

AQUEOUS MEDIUM

NAME: MUHAMMAD HAZWAN HAMIM BIN SHAHFAR AMIL

STUDENT ID: 2020997085

GROUP: AS2222A

BRANCH: UITM CAWANGAN PAHANG KAMPUS JENGKA

LECTURER: DR. AIZA HARUN

DATE OF SUBMISSION: 20/04/2021

Experiment 1

Title: Preparation of 4-vinylbenzoic acid by a Wittig reaction in aqueous medium

Section A

1. Stated MSDS all chemicals used in the experiments and suggest precaution steps need
to be taken.

Material Safety Data Sheet

Chemicals Hazard Statement Precautions Step

- Cause skin irritation - Use only in well-ventilated

- Causes serious eye area
irritation - Stored in a cool, dry place
4-Bromomethylbenzoic - May cause respiratory
acid irritation
- Contact with metals
may evolve flammable
hydrogen gas.
Triphenylphosphine - Harmful if swallowed - Wear protective gloves,
- Contains gas under protective clothing, eye
pressure and may protection and face protection.
explode if heated
- May cause an allergic
skin reaction
- Highly flammable - Keep away from
liquid and vapour heat/sparks/open flames/hot
Acetone
- Causes serious eye surfaces – No smoking
irritation
- May cause drowsiness
or dizziness
- Extremely flammable - Keep away from
liquid and vapour heat/sparks/open flames/hot
Diethyl ether
- Harmful if swallowed surfaces and other ignition
- May cause drowsiness sources – No smoking
or dizziness - Keep container tightly closed
 - Keep cool

- Harmful if swallowed - Keep away from

- May cause an allergic heat/sparks/open flames/hot
Formaldehyde 37%
skin reaction surfaces – No smoking
solution
- May cause fire or - Obtain special instructions
explosion before use

- Heating may cause fire - If exposed to skin, rinse skin

with water. Remove
Sodium hydroxide pellets
immediately and wash
contaminated clothing before
use.

- Highly flammable - Keep container tightly closed

liquid and vapour - Keep away from
Ethanol
- Causes serious eye heat/sparks/open flames/hot
irritation surfaces – No smoking

- Causes severe skin - Avoid breathing

burns and eye damage dust/fume/gas/mist/vapours/s
Hydrochloric acid
- May cause respiratory pray
irritation - Store in a dry place

2. Objectives of the experiment:

I. To prepare 4-vinylbenzoic acid by a Wittig reaction in aqueous medium
II. To obtain the yield and melting point for product and analyse the product using IR
and NMR spectroscopy.
3. Show experiment setup with complete labelling of the apparatus.
Section B

1. Calculate the theoretical mass of the ylide (4-

carboxybenzyltriphenylphosphoniumbromide) produced in the reaction.

Theoretical mass of 4-Carboxybenzyltriphenylphosphonium bromide

Number of moles for 4-Bromomethyl benzoic acid:

= mass/molar mass

= 4.30 g/ 215.1 g/mol

= 0.02 mol

1 mol of 4-Bromomethyl benzoic acid = 1 mol of 4- Carboxybenzyltriphenylphosphonium

bromide

Mol of 4-Carboxybenzyltriphenylphosphonium bromide = 0.02 mol

Molecular weight of 4-Carboxybenzyltriphenylphosphonium bromide = 477.3 g/mol

= mole X molecular weight

= 0.02 mol X 477.3 g/mol

= 9.55 g

2. Calculate mass of 4-vinylbenzoic acid if only 2.0 g of the ylide was used and assuming
only 80% of product isolated from the reaction.

Mass of 4-vinylbenzoic acid

Number of moles for 4-Carboxybenzyltriphenylphosphonium bromide:

= mass/molar mass =2.0 g/ 477.338 g/mol

= 4.19×10˄-3 mol
1 mol of 4-Carboxybenzyltriphenylphosphonium bromide = 1 mol of 4-Vinylbenzoic acid

Mol of 4-Vinylbenzoic acid = 4.19×10˄-3 mol

Molecular weight of 4-Vinylbenzoic acid

= 148.161 g/mol

= mole X molecular weight

= 4.19×10˄-3 mol X 148.161 g/mol

= 0.62 g

Actual mass of 4-vinylbenzoic acid

(y g/0.62 g) x 100% = 80%

(80% x 0.62 g) / 100%

y= 0.496g

3. In experiment 1 (preparation of ylide) ether was chosen as solvent to wash the crude
products. Explain why?
Ether was chosen as solvent to wash the crude products because it can remove
triphenylphosphine. Thus, can achieve purification.

4. Explain why concentrated acid was added onto the final filtrate towards precipitation
of crude 4-vinylbenzoic acid
Concentrated acid was added onto the final filtrate towards precipitation of crude 4-
vinylbenzoic acid because it used to protonate the organic product, causing a salt to
form which would then dissolve in the aqueous layer.
 5. Below are 2 spectra of compound A and B representing either benzaldehyde and 4-
vinylbenzoic acid

a) Identify and assign peaks(s) for compound A and B

Compound A is benzaldehyde and Compound B is 4-vinylbenzoic acid.

Compound A

Peak Wavenumber (cm-1) Type of bond

1. 2800 and 2900 C-H aldehyde

2. 1730 C=O stretch

3. 1500 C=C aromatic

Compound B

Peak Wavenumber (cm-1) Type of bond

1. 3600 O-H broad

2. 1780 C=O stretch

3. 1520 CH2 bend

4. 1300 C=C aromatic

5. 1100 =C-H vinyl

b) Choose spectra representing benzaldehyde and 4-vinylbenzoic and explain your

answer
Spectra represent the benzaldehyde are two C-H stretch at ~2750 cm-1 and 2850 cm-
1, while for 4-vinylbenzoic acid is O-H broad at 3400-2400 cm-1.

6. A B C D

E F
 i. Assign each proton labelled as (A-F) to its corresponding peak in the spectrum.

ii. Explain your reasons referring to its multiplicities and shift value.

4-Vinylbenzoic acid is an aromatic carboxylic acid. There are three distinct

groups in this molecule such as benzene ring, vinyl group and -COOH group. 2
peaks corresponding to Ar-H, 3 peaks due to the vinyl group and one peak due to
-COOH group. The peak at 6.8ppm which you are looking as quartet is actually
a dd and is due to vinyl group. There are two protons adjacent to the aromatic
protons which couple and give two doublets. The -COOH group has a great
tendency for association it gives a broad band in NMR as well as IR.

7. Draw mechanism of reaction towards synthesis of the title compounds.

Section C

References

• Ashenhurst, J. (2020, February 20). Aldehydes and Ketones. Retrieved from Master
Organic Chemistry: https://www.masterorganicchemistry.com/2018/02/06/wittig-
reaction/
• Safety Data Sheet Search. (n.d.). Retrieved from Chemical Safety:
https://chemicalsafety.com/sds-search