ORGANIC CHEMISTRY II- PRACTICAL ASSESSMENT 2

WEEK 3: 02- 06 August 2021

Technologist: D. NANHAPO

Required Materials/ sources of information: (i) Laboratory manual, (ii) Organic text books and
(iii) videos.

Report submission: Student should write a full scientific report in PDF format for each experiment
on time, and submit on Moodle. Please follow the general layout of practical reports and report
format as given in the lab manual.

Experiment 2: Coenzyme synthesis of Benzoin (Condensation reaction)

Techniques:
Synthesis,
Crystallization,

Objective: To synthesis benzoin from benzaldehyde, using thiamine hydrochloride.

Overview/Background

This experiment demonstrates a multiple synthesis of benzil, starting from benzaldehyde. In the
first part, benzaldehyde is converted to benzoin using a thiamine-catalyzed reaction. Benzoin is
later oxides to benzil using nitric acid.
The aim of this experiment is to synthesize benzoin using thiamine hydrochloride as catalyst. This
reaction is known as benzoin condensation reaction.

Thiamine hydrochloride is structurally similar to thiamine pyrophosphate (TPP), a coenzyme that

catalyzes several biochemical reactions in living systems.
Practical Assessment 2 [Total marks: 66]

Video links:

1: Thiamine hydrochloride catalyst:

https://www.youtube.com/watch?v=HIR59LMurnE

2: potassium cyanide as a catalyst:

https://www.bing.com/videos/search?q=synthesis+of+benzoin+in+the+lab&&view=detail&mid=B0332A
F08CF722753C40B0332AF08CF722753C40&&FORM=VRDGAR&ru=%2Fvideos%2Fsearch%3Fq%3Dsynthe
sis%2520of%2520benzoin%2520in%2520the%2520lab%26qs%3Dn%26form%3DQBVR%26sp%3D-
1%26pq%3Dsynthesis%2520of%2520benzoin%2520in%2520the%2520lab%26sc%3D0-
31%26sk%3D%26cvid%3D2306A14669EC42E0AAF776B0E290275E

Part A: Scientific practical report

Base on the video (links attached), write a full scientific reports on the experiment: Coenzyme
synthesis of Benzoin (Condensation reaction) with potassium cyanide as a catalyst. Give full
details, follow the report layout and format report as outlined in Lab manual, to avoid losing marks.
[50]

Part B: Post lab questions

1. In the synthesis of Benzoin experiment, KCN and thiamine hydrochloride can be used. Which
reagent will you recommend to be used in undergraduate laboratory and why? [3]
2. Consult the relevant textbooks and outline the mechanism for the thiamine-catalyzed benzoin
condensation reaction. [2]
3. Give the chemical equation for synthesis of Benzoin. [2]
4. Calculate the theoretical yield of benzoin starting from 4.5 mL of pure benzaldehyde. [3]
5. If you were to use an appropriate enzyme in this reaction, how do you think this would have
affected the reaction (degree of completion, yield and stereochemistry)? [2]
6. What modifications of conditions would be appropriate if the enzymes were to be used? [2]
7. Without re-drawing the mechanism again, explain the mechanism of the thiamine- catalyzed
benzoin condensation reaction in words. [2]