Dao 1

QuynhTrang Dao
Hanh Nguyen
April 3, 2015

Reduction of a Ketone to an Alcohol

Introduction
The reduction of carbonyl group yields primary or secondary alcohol. 1 In the
experiment, Benzhydrol will be synthesized from Benzophenone using sodium
borohydrite (NaBH4). Instead of using LiAlH4 like in theory, in reality NaBH 4 is often
used because it is less reactive with water than LiAlH 4 while LiAlH4 reacts violently with
water, and this might ruin the experiment.1
OH

NaBH4
95% EtOH

Benzop
henone

Benzhydrol

The mechanism of the reaction is based on hydride transferring. In the first step,
H detaches from BH4- ion and adds to the ketone group creating an alkoxide ion. 2 In the
second step, H in water is added to alkoxide to form alcohol.2

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Experimental
1.016g benzophenone, 15mL of 95% EtOH and a stir bar were added to 100mL
round bottom flask. The flask was gently heated in a sand bath, which was on top of the
stir plate. When benzophenone was completely dissolved, the flask was pull up from the
sand bath but still on top of the stir plate, and was let to cool down. Preliminary TLC was
taken. 0.201g NaBH4 was slowly added to the flask. After all NaBH 4 was added, 4
comparison TLCs was taken every 5 minutes (before and after NaBH 4 was added). The
flask was taken off and placed into ice bath. 0.1% HCl was slowly added to the flask for
the solution to precipitate. The solid was dried by vacuum filtration. IR spectrum was
taken with TA help. The weight of white solid was recorded to be 0.872g.

Data
Figure 1: Benzophenone and NaBH4 reaction.
OH

NaBH4
95% EtOH

Benzophenone

Benzhydrol

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Figure 2: IR Spectrum of Benzophenone

Figure 3: IR Spectrum of the solution after reaction

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Figure 4: TLC plates every 5 minutes

Before
Rf =

2.8 cm
4 cm

Before
=

2 cm
3.2 cm

0.70 Rf =

0.62
After
Rf =

After

2.9 cm
4 cm

2 cm
3.2 cm

0.72 Rf =

0.62
B

A1

Rf =

2 cm
4 cm

A2

= 0.50

Rf =

Before
Rf =

1.5 cm
3.2 cm

= 0.47

Before
2.3 cm
3.4 cm

0.68 Rf =

2.2 cm
3.2 cm

0.69

Compounds

Benzophenone

NaBH4

Formula Weight

182.22 g/mol

37.8 g/mol

A3

A4

95% EtOH

Benzhydrol

46 g/mol

184.23 g/mol

NA

Mole ratio

Mole Needed

5.49 x 10-3 mol

NA

5.49 x 10-3 mol

Quantity Needed (g or
mL)
Quantity Measured
Mp/Bp (C)

1.0 g

5.49 x 10-3
mol
0.208 g

15 mL

1.01g

1.016 g
47-51 C

0.201 g
NA

15 mL
NA

0.872g
65-67 C

Limiting Reagent

Yes

No

NA

No

After
Rf =

After
1.9 cm
3.4 cm

= 0.56 Rf =

1.7 cm
3.2cm

= 0.53

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Table 1: Reagents and properties

Percent yield=

0.872 g
100 =86.3
1.01 g

Conclusion
According to the IR spectra of Benzophenone before the reaction, there was
a strong and sharp peak in the 1680 1715 cm -1 position, which represented the Ketone
group (-CO). After the reaction, the IR spectra of the solution did not have any strong
sharp peak in that position any more, but there was a strong and broad peak in the
3370.64 cm-1 position, which represented the hydroxyl group (-OH). The IR spectrum
proved that the solution collected after the reaction was Benzhydrol.
After the first 5 minutes, there were 3 spots on the TLC plate:
one of the Benzophenone (Rf value = 0.70), and two of the reacting
solution A1 (Rf value = 0.72 and 0.50). The first spot of A1 represented
Benzophenone with approximately equal Rf values. The second spot of
A1 represented Benzhydrol. The reaction was progressing. In the
second TLC plate (next 5 minutes), there were also 3 spots, and the
results appeared to be almost the same. The reaction had not
completed yet. In the third TLC plate, there were only 2 spots: one of
the Benzophenone before reaction (Rf value = 0.68), and one of the
reacting solution A3 (Rf value = 0.56). The one spot on A3 represented
Benzhydrol, and it proved that Benzophenone was not in the solution
any more. On the forth TLC plate, there were also 2 spots. The reaction
had completed.

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The amount of Benzhydrol collected was expected to be 1.01g while in
reality, 0.872g of Benzhydrol was collected. Therefore, the percentage yield was 86.3%.
Theexperimentwassuccessful.

References
1. Thaxton,A.;Lindsay,M.;Hickey,S.OrganicChemistryLab1;2nded.;The
UniversityofNewOrleans:NewOrleans,2015;p.107.
2. Masterorganicchemistry.com,.'SodiumBorohydride:ReducingAgentFor
AldehydesAndKetonesMasterOrganicChemistry'.N.p.,2015.Web.13Apr.
2015.http://www.masterorganicchemistry.com/2011/08/12/reagentfriday
sodiumborohydridenabh4/