CHM 0053-01-P Lab Report #10

Vintus Okonkwo
TA: Xizhao Chen
Experiment #9: Reduction of an Aldehyde to Primary Alcohol

Lab Partners: Sam Boas

Date: 11/19/2015

1. Title of Experiment: Reduction of Isomeric Vanillin by Sodium Borohydride to Alcohol Derivative.

2. Purpose: An isomer of Vanillin is to be reduced by sodium borohydride to form an alcohol and the
identity of the starting vanillin isomer will be determined via melting point of the alcohol
formed. The progress of the reaction will be monitored via TLC and percent yield of alcohol
product will be derived.
3. Procedure: Please, refer to the lab handout and lab notebook #10: Reduction of an Aldehyde to
Primary Alcohol for detailed procedure followed in the experiment.

4. (a) Observations:
(i)

pH paper turned light-green at pH= 6 upon dropwise addition of adequate volume of 4M HCl.

(ii)

White precipitate was obtained as crude product after the addition of HCl as cited in (i) above.

(iii)

White product was obtained when crude product in (i) above was recrystallized in ethyl
acetate.

(iv)

TLC analysis for the recrystallized product obtained in (ii) above shows a transitional phase
from reactants only to products.

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(b.) Data and Calculations:

Mass of weighing paper = 0.2240g
Mass of weighing paper + crude product = 0.3500g
Mass of Crude Product = 0.1260g
Mass of recrystallized product = Actual Yield = 0.0300g
Reaction Scheme:

0.400g C8H8O3 x

1mol C 8 H 8 O3
152.15 g C8 H 8 O3

4 mol C 8 H 10 O3
4 mol C8 H 8 O 3

154.15 g C8 H 8 O 3
1mol C 8 H 8 O3

= 0.4100g

alcohol
Hence: Theoretical yield = 0.41g

% Yield =

Actual Yield
Theoretical Yield

x 100% =

0.0300 g
0.4100 g

x 100% = 7.31%

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5. Results:
The calculated Percent Yield of the recrystallized product was 7.31% (Data and Calculations). Melting
point analysis for the recrystallized product determined its melting point range as (113.4 114.6) C
(Table 1) which is very close to that of vanillin alcohol found in literature, (113 115) C. Hence,
starting aldehyde was identified as Vanillin. Four TLC analysis for the recrystallized product yielded
various Rf values and composition over time intervals of 10mins: starting aldehyde at time t =1mins, a
mixture of starting aldehyde, alcohol derivative and side product impurity at time 10mins < t < 20mins,
alcohol derivative at time t = 30mins (Figure 1).

Compound

Temperature (C)

Ramp Rate

Observation

..
90
Alcohol

113.4

Start temperature
5C/min

First crystal melted

113.9

Sample half melted

114.6

Last crystal melted

Table 1: Melting point analysis for Unknown#5 aldehyde

Figure 1: TLC Analysis for recrystallized product from Sample V

Four TLC analysis was carried out in total, two reference standards were used: the aldehyde reference, and
the alcohol reference both for Unknown#5. The mobile phase used was 10% ethyl acetate in hexane.
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6. Discussion:
To recap, this experiment aimed to synthesize alcohol derivatives of marked aldehydes by
reduction with sodium borohydride and also to determine the identity of the starting aldehyde via the
melting point and track the progress of the reaction through TLC analysis. An aldehyde is converted
into its alcohol via reduction (Reaction 2) and hence requires a reducing agent. Sodium borohydride is
a common reducing agent that can be used to reduce ketones and aldehydes into secondary and primary
alcohols respectively (as exemplified in Reaction Mechanism 1).

CHM 0053-01-P Lab Report #10

In this experiment the aldehyde used is one of three isomers of vanillin (C 8H8O3) and the product is the
corresponding alcohol (C8H10O3). The progress of the experiment was monitored over thirty minutes
via TLC analysis (figure 1) to determine when all the starting isomeric aldehyde, vanillin, had been
reduced into its analogous alcohol. The eluted spots on the TLC plates were visualized under short UV
lamp as they did not exhibit any obvious color. As Sodium borohydride is stable under alkaline
conditions, sodium hydroxide was added to make the reaction mixture alkaline. It was also important
that dil. HCl was added to acidify the water present and release the alcohol from the complex ion
formed from aldehyde reduction. It also neutralizes the excess sodium hydroxide base. After the crude
product obtained from this procedure was recrystallized, melting point analysis show that the alcohol
formed having melting point range of (113.4 114.6) C can be identified as vanillin alcohol which
further indicated that the aldehyde sample used was vanillin. Also, TLC analysis for the recrystallized
product show that at the end of 30mins, all the vanillin aldehyde had been reduced to vanillin alcohol
as the Rf value for the product mixture was similar to that of the reference starting vanillin aldehyde at
time = 1min, and the Rf value gradually matched up with that of the reference alcohol after 30 mins
(Figure 1). The choice of solvent used in the TLC analysis was 10% ethyl acetate in hexane as this ratio
of ethyl acetate to hexane is optimal to yield a reasonable Rf values (both starting aldehyde and final
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CHM 0053-01-P Lab Report #10

alcohol product are polar and will tend to travel gradually on the polar stationary phase and not quickly
with the almost non-polar solvent). The alcohol product is more polar than the aldehyde and thus
travels slower on the TLC plate, hence it has a lower Rf than the starting aldehyde. The third spot on
the TLC plated II and III is likely due to boric acid formed during the workup of the experiment.
7. Conclusion:
At the end of the experiment, the percent yield of the recrystallized alcohol derivative was determined
as 7.31%. Melting point analysis for the recrystallized product was obtained as (113.4 114.6) C
(Table 1) which is very close to that found of vanillin alcohol found in literature, (113 115) C.
Hence, starting aldehyde is identified as Vanillin. TLC analysis for the recovered alcohol product
showed a transition in reduction of vanillin to vanillin alcohol with the persistence of a side product
impurity. A better result would be obtained by properly recrystallizing the alcohol product formed as
boric acid is insoluble in ethyl-acetate.

8. References:
Macroscale and Microscale Organic Experiments; Williamson, K., Masters, K.; 6 th Edition; Cengage
Learning, International Edition, 2011.
Chemistry 54 Organic Chemistry Laboratory: Synthesis of Diphenylacetylene; Tufts University,
Medford, 2015.

9. Post-Lab Questions:
1.

4 C8H8O3 + NaBH4 + 4H2O ------> 4 C8H10O3 + H3BO3 + NaOH

Molar ratio of aldehyde to NaBH4 reacting = 4:1

1mol C 8 H 8 O3
C8 H 10 O3
0.400g x 152.15 g C8 H 8 O 3 = 0.00262 moles
added

CHM 0053-01-P Lab Report #10

0.050g x

1 mol NaB H 4
37.83 g NaB H 4

= 0.00132 moles NaBH4 added

Molar ratio of aldehyde to NaBH4 added = 2:1

2.

3. NaOH was added to the reaction mixture to make the solution alkaline as NaBH4 is stable in alkaline
condition.

1. Benzene

CHM 0053-01-P Lab Report #10