EXERIMENT 2

SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXANONE

OBJECTIVE

 To synthesize cyclohexanol from cyclohexanone by using reduction reaction with

sodium borohydride.
 To determine the percentage yields of product produce.

INTRODUCTION

In organic chemistry, a ketone is a compund with the structure RC(=O)R', where R

and R'can be a variety of atoms and groups of atoms. It features a carbonyl group (C=O)
bonded to two carbon atoms and the oxygen center is more electronegativity than that for
carbonyl carbon. Thus, ketones are nucleophilic at oxygen and electrophilic at carbon.
Ketones are converted to alcohols by reduction with sodium borohydride followed by
hydrolysis in an aqueous acidic workup. In this reaction, a hydride anion from the
borohydride is transferred to the electropositive carbon of the carbonyl group. Sodium
borohydride were used in this experiment because it is easier to be handled The reaction of
cyclohexanone with sodium borohydride is demonstrated in the following equation:
APPRATUS

 Test tube
 Ice bath
 Pasteur pipette
 Round bottom flask
 Rotary Evaporator

CHEMICAL

 5mL of methanol
 2mL cylohexanone
 200mg sodium borohydride
 5mL of 3M Sodium hydroxide solution
 4mL distilled water
 5mL dichloromethane
 Anhydrous Sodium sulphate

PROCEDURE

1. 5 mL of methanol was placed in a large test tube and 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, sodium borohydride was weighed and 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, sodium hydroxide solution was added to decompose the borate
ester and 4mL of water was added to the solution.
4. The product was separated as clear layered . By using pasteur pipette the clear layer
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 and using the seperatory funnel about 2 times.
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 reweighed and the percentage yield of product was calculated.
9. The IR spectrum of your spectrum was obtained
RESULTS

The mass of round bottom flask 54.8440 g

The mass of round bottom flask + product 58.3980 g
The mass of product (cylohexanol) 3.5540 g

DISCUSSION

In this experiment, the reduction step of the ketones to alcohol is the transfer of a
hydride ion from the metal to the carbonyl compound. The percentage yield of the product
is 97.59%. The reducing agent in this experiment is sodium borohydride and the
cyclohexanol are the product obtained. We used methanol as a solvent to detect whether
sodium borohydride is can do the reaction. In this experiment we can see the sodium
borohydride is active in reducing the cyclohexanone to cyclohexanol. This is because there is
vigorous reaction when we added sodium borohydride in the methanol with 2mL of
hexanone.

The experiment is success, even we do not get 100% percentage yield but we still get
97.59% which is near to the 100% yield. This may causes by few error while we are handling
the experiment. Firstly, after we added the sodium borohydride into the methanol with
cyclohexanone make sure the reaction are complete. If there still have bubble that’s mean
the reaction are not complete. Make sure to always to put in the ice bath. There is some
precaution while we are handling the experiment. Sodium borohydride may be dangerous
to us, before we do the experiment we should really understand the steps and the quantity
of the reducing agent should be used. The most important thing is to wear goggle in the lab
because the hazardous chemical can harm us.

CONCLUSION

From the experiment, ketone group can be converted into alcohol group by using
reduction reagent sodium borohydride. This experiment was successful in reducing the
cyclohexanone because from the IR spectrum result we can observed the presence of
cyclohexanol.

REFERENCES

T.R Hoye. (2018) Ketone reduction by sodium borohydride. Retrieved from

http://www1.chem.umn.edu/groups/hoye/teaching/Teaching2312HFall2018/1KetoneR
educeF18.pdf

Pavia., L Donald. A small scale approach to Organic Laboratory Technique. Fourth edition pg
(610-614)
 CHM 556

Organic Chemistry II ( Laboratory Report)

Experiment 2

Sodium Borohydride Reduction Of cyclohexanone

Name : Rasyiqah Binti Abdul Rani

Student No. : 2017442676

Date of experiment : 1 st October 2018

Date of submission : 8th October 2018

Lab Partner’s Name : Nur Afiqah Nadhiah Binti Ammar Rusdan

(2017442658)
Lecturer’s Name : Dr. Syahrul Imran