Title : Sodium Borohydride Reduction of Cyclohexanone.

Objective

1) To investigate the reduction reaction of ketone to an alcohol using sodium

borohydride as the reducing agent .
2) To study what is the expected ketone and the expected product
3) To study what is the reducing agent

Introduction

Carbonyl group is the key of many functional groups such as aldehydes , ketones ,
amides and others. One of the reaction in carbonyl group is nucleophilic addition.The
carbonyl group consists of partial positive and partial negative atom.The nucleophile attack
the partial positive atom which is carbon , so , the electron at carbon-oxygen shift to the
oxygen which cause the oxygen aton become negative and the carbon atom become
positive in their charge.The positive charged atom was added with hydride ion from sodium
borohydride compound.

Reduction of organic molecule usually corresponds to increasing its hydrogen content

or to decreasing its oxygen content.In this experiment ketones was reduced to alcohol.
Reducing agent for ketones to alcohols is lithium aluminium hydride ( LiAlH4) and sodium
borohydride ( NaBH4). LiAlH4 is strong reducing agent . It can reduces esters , acids ,
aldehydes and ketones while NaBH4 can reduces aldehydes and ketones . LiAlH4 can react
vigorously in water , so , the experiments cannot be carried out in water or alcohols solution
while NaBH4 experiment can carried out in water and alcohol solutions . The reducing agent
in this experiment is NaBH4 , the expected product in this experiment is cyclohexanol which
is formed from cyclohexanone.
Experimental method

1) 5 mL of methanol was placed in a large test tubeand 2 mL of cyclohexanone was

added into the large test tube and the test tube was cooled in an ice bath.
2) 200 mg of NaBH4 was added into the solution . After the vigorous reaction has
ceased ,the test tube was removed from the ice bath and the test tube was allowed it
to stand at room temperature for 10 minutes.
3) 5 mL of 3 M NaOH solution was addded to decompose the borate ester and 4mL of
water was added to the solution.
4) The product was separated as small and clear upper . By using pasteur pipette was
transferred as much of the product to another clean test tube.
5) The remainder product was extracted from the reaction mixture using 5 mL of
dichloromethane .
6) The dichloromethane was combined with the earlier product layer and dried with
anhydrous sodium sulphate .
7) Small clean pre weighed round bottomed flask was transferred and the
dichloromethane was evaporated using evaporator .
8) The flask was reweigh and the percentage yield of product was calculated.
9) The IR spectrum of your spectrum was obtained .
Results and observation

The mass of round bottomed flask = 46.3730 g

Mass of cork = 17.3885 g

Mass of product with round bottomed flask = 65.4187 g - 17.3885 g

= 48.0302 g

Mass of product = 48.0302 g - 46.3730 g

=1.6572 g

Percentage yield formula = actual yield x 100%

Theoretical yield

Mass of cyclohexanol

Molecular mass = 100.158 g/mol

No.of mole of cyclohexanol

Density = mass / volume

0.9478 g/mol = mass / 2 mL

Mass = 1.8956 g

Percentage yield

= 1.6572 g x 100%

1.8956 g

= 87.4 %
Discussion

The reduction step of the ketones to alcohol is the transfer of a hydride ion from the
metal to the carbonyl compound . The hydride ion act as nucleophile and the mechanisms for
reduction of cylohexanone to cyclohexanol by sodium borohydride is as shown below :

The percentage yield of the product is 87.4 % .The reducing agent is NaBH4 and
cyclohexanol is the expected product .Cyclohexanone and cyclohexanol have different
solubility in water .In this experiment methanol is a solvent and it also used to detect wether
the NaBH4 active or not to do the reaction. If there is vigorous reaction so the NaBH4 is active
and can be used to reduced cyclohexanone to cyclohexanol. NaBH4 is not very strong
reducing agent because it only can reduced ketone and aldehyde .

The density of cyclohexanol is higher compared to aqueous solution , so , while

handling the experiment we take the bottom layer liquid to further the experiment.The
remainder product was extracted two times to make sure there is no left any cyclohexanol in
the separatory funnel. Anhydrous sodium sulphate is used to absorb the moisture and the
product were evaporated using rotoevaporator .

The experiment is success, even we do not get 100% percentage yield but we still get
87.4% which is near to the 100% yield.This may causes by few error.While we are handling
the separatory funnel , the funnel was broken and there is some of our product we released
fro the funnel so we cannot get the correct percentage of the product . There is some
precaution while we are handling the experiment. NaBH4 may be dangerous to us , before
we do the experiment we should really undestand about the steps and the quantity of the
reducing agent should be small. The most important thing is to wear goggle in the lab
because the hazardous chemical can cause us blind.If the acid or bases get into our eyes ,
flush it out immedietly with lots of water until it the chemical was removed.It ts the same ,
when other place part of our body was spilled with chemical , flush the area with water and
the sink or use the safety shower in the lab.
Conclusion

The reduction reaction of cyclohexanone was performed .The expected product is

cyclohexanol ,based on the IR spectrum we get cyclohexanol. The reducing agent in this
experiment is sodium borohydride , NaBH4 .

References

1) http://www.gobookee.org/get_book.php?u=aHR0cDovL3d3dy54dWxhLmVkdS9jaGVtaXN0cn
kvZG9jdW1lbnRzL29yZ2xlY2xhYi8xOVJlZG94LnBkZgpPeGlkYXRpb24gb2YgQ3ljbG9oZXhhbm9s
IHRvIEN5Y2xvaGV4YW5vbmU=
2) Donal L . Pavia ; Gary M. Lampman;George S Kriz;Randall G Engel , A microscale
approach to organic laboratory techniques , fifth edition , published by Belmont/Cole ,
Cengage Learning ,[2013] , page : 550,552,553,554 and 555.

Laboratory techniques

The techniques involves in this experiment is separation and distillation.

 Full marks Mark (to be filled by the
lecturer)
Objective of the 1.0
experiment
Introduction 2.0
Experimental procedure 1.0
Results and observations 3.0
Calculations 3.0
Discussions 2.0
Conclusions 1.0
Answers to the question 3.0
References 1.0
Pre-laboratory 2.0
preparations
Laboratory techniques 1.0
Total marks 20.0
APPLIED CHEMISTRY
AS2253A
EXPERIMENT 2 : SODIUM BOROHYDRIDE REDUCTION OF
CYCLOHEXANONE
NAME:IDAYU BT RAZALI
NAME OF PARTNERS:MONICA LIMAU ANAK JADAM
LECTURER NAME:PROF. FARIDAHANIM
DATE OF EXPERIMENT:1/10/2013
DATE SUBMISSION REPORT:8/10/2013