RATIFICATION PAGE Complete report of Organic Chemistry I with the title Preparation of Cyclohexanone which made by: Name

: Sri Agustiani Basir

Reg. Number : 101304159 Class Group Department : ICP Chemistry : IV : Chemistry

After checked by assistant and assistant coordinator. So, this report accepted.

Makassar, June Assistant coordinator Assistant

2011

(Ahmad Fudhail Majid, S.Pd ) Known by, Lecturer of Responsibility

( Widiastini Arifuddin, S.si)

( Iwan Dini, S.Si, M.Si )

A. Title of experiment Title in experiment is Preparation of cyclohexanone

B. Purpose of experiment Purposes in experiment are: 1. Have a skill to do oxidation of secondary cyclic alcohol 2. Can understand about oxidation reaction of secondary cyclic alcohol

C. Preview of literature Cyclohexanone is the six member alicyclic hydrocarbon consisting of six carbon atoms linked to each other to form a ring, with each carbon atoms, C6H12. Acyclic compound is an organic compound that consists of one ear more closed rings of atoms carbon. The term alicyclic refer to cyclic compound that behaves chemically like aliphatic compounds (open-chain), which means the exclusion of carboxylic compounds of aromatic rings with an array of electrons characteristic. Cyclohexane is colorless, highly flammable, mobile liquid with a pungent odor. It is insoluble in water and soluble in alcohol, ether and almost organic solvents (Anonym, 2011). Cyclohexane is a non-corrosive and quick volatilize liquid and sublimes between -5 to 5 C. Cyclohexane can exist in a number of inter convertible threedimensional conformations, the two simplest being are the chair and boat conformation and others include the half-chair and twist-chair conformation. Cyclohexane can cause irritation to the eyes and mucous membranes in workers. Repeated and prolonged contact with skin may cause dermatitis. The substance has not been shown to cause the hematologic changes associated with exposure to benzene. Cyclohexane occurs naturally in crude oils. Some cyclohexane is recovered from petroleum streams by fractionation. The bulky commercial production of cyclohexane is based on hydrogenation of benzene in closed

system. Cyclohexane consumption is linked almost entirely to nylon production. Nylon is further processed into fibers for applications in carpeting, automobile tire cord, clothing, and other growing industrial fields. Cyclohexane is used as a solvent, oil extract ant, paint and varnish remover, dry cleaning material, and in solid fuels. It has been used as an insecticide itself. Cyclohexane is used as a chemical intermediate to produce target molecules. Natural compounds of one to five alicyclic rings with great variety and complexity are found particularly in steroids and trepans. Cyclohexane structure, six member-rings, is one of the major skeletons in nature. Cyclohexane derivatives can be used for the synthesis of pharmaceuticals, dyes, herbicides, plant growth regulator, plasticizers, rubber chemicals, cyclamens and other organic compounds (Anonym, 2011). The general formula of mono hydroxide alcohol group is ROH, certainty that R can have a form alkyl group, unsaturated alkyl, substituted alkyl, and possibly also cyclic chain. In addition it is also known alcohol group, containing more than one group OH. Alcohol structural diversity can be seen from the following examples: CH3CH2CH2OH CH2 = CHCH2OH
CH 2 - OH

OH

CH 2 - CH 2

HO

OH

Alcohol functional group is a group class OH (hydroxyl) and groups that determine the properties of his trademark. Diversity structure of carbon atom chains that bind OH, alcohol groups can be grouped into: 1. Primary alcohol, -OH bound C atom primary, 2. Secondary alcohol, -OH bound C atom secondary, and 3. Tertiary alcohol, -OH bound C atom alcohol tertiary. Examples from groups are: CH3CH2OH
CH 2 - OH Primary alcohol

Primary alcohol

CH3CHCH3 OH CH3 H3C C CH3 OH

Secondary Alcohol

Tertiary alcohol

When viewed from the number of groups OH contained in each structure, the alcohol group can be divided into monohydrocsyl alcohol (which has one group OH), alcohol hydroxyl (which has two groups OH), and onwards (Parlan, 2005:115-117). Alcohol can form hydrogen bond between molecules, melting point alcohol higher than melting point halide alkyl or ether, which its proportional molecular weight. Low molecular weight alcohol soluble in water, whereas the corresponding alkyl halides are not soluble. Solubility in water is directly caused by hydrogen bonds between alcohol and cloroalkane (Ralp, 1999:160-161).

According to Brady (1990:768) aldehydes and ketones have something in common; they both contain a carbon oxygen double bond, C=O. This groups of atoms is called a carbonyl groups. H RC=O Aldehyde O R C R Ketone

Formaldehyde, of course, is used in preserving biological specimens and for embalming. It also used in the manufacture of some plastics. Some important ketones are: O CH3 C CH3 O CH3 C CH2CH3

Oxidant commonly used in laboratories for this purpose is chromic acid. H2CrO4 (lowered from K2CrO7 and strong acid) and CrO3 contain Cr6+. Example oxidations become cyclohexanone (Muhaidah, 2009:137).

D. Apparatus and Materials 1. Apparatus a. Erlenmeyer 250 mL b. Distillation flask 500 mL c. Condenser d. Funnel f. Thermometer 3000 = 1 piece = 1 piece = 1 piece = 1 piece

e. Volumetric glass 10 mL, 100 mL = 1 piece = 1 piece

g. Beaker glass 250 mL, 1000 mL = 1 piece h. Separating funnel 250 mL i. Stir bar j. Spray bottle k. Boiling stone l. Statif and clem m. Balance n. Drop pipette o. Closed Erlenmeyer 2. Materials a. Potassium Chromate (K2CrO4) b. Concentrated H2SO4 c. Cyclohexanol (C6H11OH) d. H2O e. NaCl f. Petroleum ether (C4H10O) g. MgSO4 anhydrate h. Tissue i. Filter paper = 1 piece = 1 piece = 1 piece = 3 pieces = 1 piece = 1 piece = 4 pieces = 1 piece

E. Work procedure 1. Dissolved 20,5 gr of potassium chromate in 100 mL of water 2. Added carefully 10 mL of concentrated H2SO4 and cooled until 300C 3. Put 10 mL of cyclohexanol in Erlenmeyer that has a flug. Added little by little mixture of potassium chromate + H2SO4 and shake. Arrange so that temperature still 500 600C. 4. Put the mixture in distillation flask and added 100 mL of water 5. Distillated the mixture, so we can get 65 mL distillate

6. Put the distillate in separation funnel, until 2 layers 7. Saturated the mixture with 13 gram NaCl, separated cyclohexanone layer and extracted with 12 mL C4H10O 8. Added 3 gr of magnesium sulfate anhydrate 9. Filtered

F. Observation result 20,5 gram of K2CrO4 + 100 mL of H2O Yellow solution + 10 mL of H2SO4 Concentrated of red solution + 10 mL of cyclohexanol old green solution temperature constant at 520C mixture + 100 mL of H2O 65

mL of distillate (form 2 layers; up layer is like oily and down layer is water) distillate + 13 gram of NaCl solution like oily (cyclohexanone) layer of like oily

and water

water + 12 mL of petroleum ether

(cyclohexanone) + 13 gram MgSO4

7,8 mL of cyclohexanone.

G. Data analysis Mm of cyclohexanol (C6H11OH) Mm of cyclohexanone (C6H10O) Mass of cyclohexanol = 6(12) + 11(1) + 16 + 1 = 100 gr/ mole = 6 (12) + 10 (1) + 16 = 98 gr/ mole = Density x Volume = 0,9620 gr/ mole x 10 mL = 9,62 gr Mole of cyclohexanol Mole of cyclohexanol = Mole of cyclohexanone = =

= 0,0962 mole Mass of cyclohexanone = Mole C6H10O + Mm C6H10O = 0,0962 mole x 98 gr/ mole = 9,4276 gr Mass of practicum = Density x volume = 0,9478 gr/ mole x 7,8 mL = 7,4 gr Rendement = = = 78,7234 % = 79%

H. Discussion This experiment will make a cyclohexanone solution with way reacted cyclohexanol with oxidizing agent of potassium chromate. Potassium chromate diluted in water produces yellow solution. In this case potassium chromate is oxidizing agent in acid situation. After that added to sulfuric acid which function as catalyst and to give acid condition in solution, the color of solution to become red solution. Existence of change of color to show that potassium chromate can react with sulfuric acid. Then cooled until 300C so that at the time of addition cyclohexanol the mixture temperatures do not too high. So that the reaction between used reagent to happen completely so get product to use. And then adding to cyclohexanol to change the color solution become old green, shaking while mixing make the mixture temperature always change. Therefore temperature has to be taken care of among 50 600C because this temperature is happened optimum temperature of oxidation. If more than temperatures, so cause the mixture become broken so that wormed of compound which produce not

cyclohexanone but other compound. The constant temperature which obtained is 520C. Adding to water at mixture, then distillation. Before distillation the mixture added boiling stone which function to decrease explosion which happened in distillation. The mixtures of distillation without using thermometer for the pressure in mixture at distillation occur more efficient for to decrease of vaporizing. The result of experiment is 65 mL formed two layers; up layer like oil and down layer is water. Caused there are different of density, the density of cyclohexanone is smaller than water (water: 1 gr/mL and cyclohexanone: 0,9478 gr/mL). Then the cyclohexanone separated from water solution with to saturate the mixture with NaCl salt, the function of addition NaCl is to saturate solution for can explain to layers between water and cyclohexanone. Extraction of water layer with petroleum ether is to bond cyclohexanone and to release of water. Petroleum ether is a solvent of non polar which form mixture of hydrocarbon liquid which characteristic an easy vaporize. Petroleum ether will dilute which compounds the characteristic less polar. And then added MgSO4, the function of MgSO4 is to bound of water. After that, filter the solution so get pure cyclohexanone 7,4 gr. Result of obtained different with theory which should 9,4 gr. This condition caused at shaking result of temperature just 520C. The rendement obtained 79%. Rendement is ratio between weighty of cyclohexanone which obtained with weighty cyclohexanone base theory which expressed with percent. Rendement cyclohexanone 79% mean from 100 gr cyclohexanone wishing to be obtained just 79 gr which produced. The reactions are:

I. Closing a. Conclusion 1. Cyclohexanone is oxidation of secondary cyclic alcohol become cyclic ketone with use K2CrO4. There are three techniques of purifying which to do, which is distillation, extraction, and filtering. 2. Cyclohexanone which found in the experiment is 7,4 gr with rendement 79% b. Suggestion 1. We hope to laboran to prepared to best quality of tools and materials in the experiment 2. We hope to practicant must be consent in practicant so result is more accurate and right.

BIBLIOGRAPHY

Anonym. 2011. Cyclohexanone. http://cyclohexanone.htm. Online. Accessed on May 4th 2011. Brady, James. 1990. General Chemistry. New York: Wiley. Parlan, Wahjudi. 2005. Kimia organic I. Malang: Penerbit Universitas Negeri Malang. Ralp J, Joans S. 1999. Kimia Organik Edisi Ketiga. Jakarta: Erlangga. Rasyid, Muhaidah. 2009. Kimia Organik I. Makassar: Badan penerbit Universitas Negeri Makassar.

ANSWER THE QUESTION

1. How to explain that the below reaction is oxidation reaction? Answer:

In equation of cyclohexanone former from cyclohexanol with potassium dichromate as oxidation in acid condition, release or loosing hydrogen, so that the molecule occur oxidation.

2. Why the reaction temperature way not higher than 600C? Answer: Because its may cause the mixture by destroy so that be worried the compound which resulted not cyclohexanone but be other compound. 3. Explain 3 manner separation technique of organic experiment! Answer: a. Distillation is a process of mixture separation based on boiling point difference in the certain pressure. These processes follow evaporation process by cooling. b. Extraction is substance separation from a mixture by adding the serration solvent. c. Filtration is the process of substance separation from a mixture based on measure of substances particles.