Short report of experiment 3: Phase-Transfer-Catalysed Oxidation of alcohols
Name : Tymo Zwakenberg
S-number : 4326253
TA : Isaac & Isabella
Date : 17-05-2023
Figure 1: Overview of the mechanism of the performed reaction.
Table 1: Overview of the used compounds during the experiment.
Compound g/mol g or mL mmol eq
Benzyl alcohol 108.14 0,96 ml (1.00g) 9.247 1
Ethyl acetate 88.11 25 ml (22.55g) 255.93 0.036M
Sodium hypochlorite 74.44 25 ml (30.875g) 414.76 44.85
Tetrabutylammonium 322.37 0.50g 1.55
bromide
Magnesium sulfate 120.37 n.w.
Benzaldehyde 106.12 0.86g 8.1 0.876
Introduction
The idea of the experiment is to get acquainted with phase-catalyzed oxidation reactions, to be
able to perform a liquid-liquid extraction and to use the rotatory evaporator. In this case it is
an oxidation reaction of benzyl alcohol to form benzaldehyde under influence of bleach
(sodium hypochlorite). Characterized through NaOCI that oxidizes the alcohol, and the
tetrabutylammonium bromide as a phase reagent makes sure the reaction can take place. By
means of TLC the reaction will be monitored, and via liquid-liquid extraction combined with
the use of a rotatory evaporator, the aldehyde will be formed and can be analyzed with IR.
Results and Discussion
Yield of oil obtained after extraction
(milli)grams : 0.86g
mmol : 8.1
Yield % : 86%
Name : Tymo Zwakenberg
S-number : 4326253
TA : Isaac & Isabella
Date : 17-05-2023
Figure 1: Overview of the mechanism of the performed reaction.
Table 1: Overview of the used compounds during the experiment.
Compound g/mol g or mL mmol eq
Benzyl alcohol 108.14 0,96 ml (1.00g) 9.247 1
Ethyl acetate 88.11 25 ml (22.55g) 255.93 0.036M
Sodium hypochlorite 74.44 25 ml (30.875g) 414.76 44.85
Tetrabutylammonium 322.37 0.50g 1.55
bromide
Magnesium sulfate 120.37 n.w.
Benzaldehyde 106.12 0.86g 8.1 0.876
Introduction
The idea of the experiment is to get acquainted with phase-catalyzed oxidation reactions, to be
able to perform a liquid-liquid extraction and to use the rotatory evaporator. In this case it is
an oxidation reaction of benzyl alcohol to form benzaldehyde under influence of bleach
(sodium hypochlorite). Characterized through NaOCI that oxidizes the alcohol, and the
tetrabutylammonium bromide as a phase reagent makes sure the reaction can take place. By
means of TLC the reaction will be monitored, and via liquid-liquid extraction combined with
the use of a rotatory evaporator, the aldehyde will be formed and can be analyzed with IR.
Results and Discussion
Yield of oil obtained after extraction
(milli)grams : 0.86g
mmol : 8.1
Yield % : 86%
