I. II.

TITTLE OF EXPERIMENT PURPOSE OF EXPERIMENT student are expected to :

: Making of Iodoform : At the end of experiment,

a. Synthesize compound of iodoform b. Purifying of iodoform by recrystallization

III.

BASIC THEORY Iodoform, or triiodomethane (CHI3) is yellow crystalline with a

relatively high molar mass due to the iodine atoms. It is therefore a solid at room temperature It melts at 119C and is very slightly soluble in water and soluble in ether or ethanol. A visible precipitate of this compound will form from a sample only when a methyl ketone is present. This type of reactivity conforms to the more general Haloform Reaction. Iodoform was formerly used as an antiseptic. It is a stable compound. Incompatible with strong oxidizing agents, reducing agents. May explode when heated. It is harmful if swallowed, inhaled or absorbed through skin and causes irritation to skin, eyes and respiratory tract. Iodoform is also affects cardiovascular system, central nervous system, liver and kidneys. When released into the soil, iodoform may leach into groundwater. When released into water, it may evaporate to a moderate extent and it is expected to have a half-life between 1 and 10 days. Iodoform has an estimated bioconcentration factor of less than 100. This material is not expected to significantly bioaccumulate. When released into the air, it may be moderately degraded by reaction with photochemically produced hydroxyl radicals and it is expected to have a half-life of greater than 30 days. Formation of Iodoform:

Iodoform is produced when a methyl ketone, acetaldehyde, or an alcohol with the formula RCHOHCH 3 is treated with sodium hydroxide and iodine. "R" can be a hydrogen atom or a hydrocarbon group (for example, an alkyl group). If "R" is hydrogen, then you have the aldehyde ethanol, CH3CHO. Ethanol is the only aldehyde to give the triiodomethane (iodoform) reaction. If "R" is a hydrocarbon group, then you have a ketone. Lots of ketones give this reaction, but those that do all have a methyl group on one side of the carbon-oxygen double bond. These are known as methyl ketones. Compounds that are easily oxidized to acetaldehyde and methyl ketones also give a positive iodoform test. Only ethanol can be oxidized to acetaldehyde and secondary alcohols that have the general formula CH3CHOHR can be oxidized to methyl ketones For ethanol (CH3CH2OH), the following reactions show the formation of iodoform : CH3COCH3 + 3 NaClO + 3 KI CH3COCl3 + 3 NaOH + 3 KCl CH 3COCl3 + NaOH CH3COONa + CHI3

IV.

TOOLS AND MATERIALS Tools :

200 mL Erlenmeyer Graduated cylinder Buchner Funnels Funnel Electric stove Filter paper Spatula

Materials : Iodoform Acetone 2 N NaOH Alcohol aquades 2,5 gram Iodium

Entered into erlenmeyer 200ml Added 2,5 mL of acetone Added 5 mL of aquades Shaked Added NaOH 2N solution drop by drops, and shaked until formed yellow precitate Shake until form yellow precipitate Added 125 ml aquades Filtered using buchner funnel

Filtrate

Residu Washed the precipitate with water until free from NaOH Iodoform Impurities Put into erlenmeyer flask that has been closed with glass funnel

V.

PROCEDURE

Put 5 ml ethanol from the funnel (keep away from flame) Heated and shaked Filtered

Filtrate

Residu Cooled Added 12,5 ml of aquades Filter by using Buchner Funnel Wash with some drops od cold ethanol Dried iodoform crystal using desicator Crystal of Iodoform Determined the mass and melting point

The mass of iodoform

The melting point of iodoform

VI.

OBSERAVTION DATA Procedure Hypothesis Result

Before Reaction The color of : Iodoform=silver solid Acetone=colorless NaOH=colorless Etanol=colorless After reaction The color of : Iodoform+acetone=dark with precipitate Iodoform+acetone+9,5 ml NaOH=yellow solution with precipitate *after recrystallization the solution dissolve *after filter=yellow crystal of iodoform *weight of crystal iodofom=0,6427 g

Conclusion Weight of iodoform crystal= 0,6427 gram Melting point of iodoform crystal=116oC

3I2(s) + CH3COCH3(aq) 3HI(aq) + CI3COCH3(aq) CI3COCH3(aq) + NaOH(aq) CHI3(aq) + CH3COONa(s)

VII.

ANALYSIS AND DISCUSSION

In this experiment, that had been done of balancing Iodium as main compound in iodoform synthetic that dissolved with H2O and added by acetone .Resulting dark colored solution, the reaction:

3I2(s) + CH3COCH3(aq) 3HI(aq) + CI3COCH3(aq)

The dark solution was then added 9,5 mL of 2N NaOH. 2N NaOH solution is a colorless solution. After the addition of 9,5 mL of 2N NaOH solution and then shaken to produce yellow, with the reaction:

CI3COCH3(aq) + NaOH(aq) CHI3(aq) + CH3COONa(s)

The solution mixture was added to 125 mL H2O. Then the filtering is done using a Buchner funnel. The screening results obtained yellow precipitate. Screening results in the form of a yellow precipitate were placed in a closed Erlenmeyer glass funnel. The next few mL of ethanol was poured through a funnel. The addition of ethanol which is a colorless solution gave no color change in the solution, which remains a yellow solution. Results are then heated while mixing whipped over an electric heater. Mixture was heated produces a yellow color (+ + +). Filtering is then performed using a Buchner funnel, and produces a yellow precipitate. Then covered and left in the cold. After getting the cold, added 12.5 mL H2O and stirred to precipitate iodoform thereafter. Filtering is done using a Buchner funnel. Filtering is done repeatedly with the aim that the results obtained maximum sediment. The screening results obtained yellow precipitate. The precipitate is then washed with a few drops of cold ethanol. Then dried in a desiccator, with the aim of iodoform crystals produced completely dry. After three days of drying in a desiccator, weighed iodoform crystals, producing 0.642 grams iodoform crystals. Then calculated the melting point of iodoform mass produced using a capillary tube and heated in electric stoves produce a melting point of iodoform is 116oC. the melting point is less than theory, because we not accurately when measured the melting point using melting block, so the result not suitable with the theory.

Iodoform crystal mass resulting from the experiment will be compared with the theoretical masses. The calculation is as follows:

Reaction: 3I2 Initial: React: Rest : 0,00328 mol 0,03086 mol + CH3COCH3 CH3COCI3 + 3HI 0,00328mol 0,00328mol -

CH3COCH3 + NaOH Initial: React: 0,03086 mol mol mol mol

CHI3 -

CH3COONa -

mol

mol

Rest:

0,01186 mol

mol

mol

VIII. CONCLUSION
The resulting crystals are yellow iodoform 0.64267 grams, while the results of theoretical mass of crystalline iodoform 2,405 grams. Percentage obtained was 26,472% mass yield and melting point of 116
o

C.

REFERENCES
Anonim. Ester. http://id.wikipedia.org/wiki/Ester. Diakses pada hari

senin, pukul 21.00 Fessenden RJ. Fessenden JS. 1991. Kimia Organic, Edisi ketiga terjemahan A. Harayana Dudjaatrata, Jilid 1 dan 2. Jakarta: Penerbit Erlangga. Tim Dosen Kimia Organik. 2013. Panduan Praktikum Kimia Organik I. Surabaya : jurusan kimia FMIPA UNESA.

ATTACHMENT

PICTURE

NOTE

Mixtured after added NaOH 2N

Iodium+aquades+acetone

The precipitate of iodoform after filter by buchner funnel

The result from recrystalization process

Answer of Questions 1. Write the reaction in the experiment

2. Explain the halogenation process for preparing iodoform beside using iodium, for example using chlor (Cl)!

3. Beside with acetone, oidoform can be prepared from ethano. Explain the reasons! Because when ethanol be oxidized it will produce a substance that has methyl aldehyde.

4. Explain the way to increase the rate of dissolving iodium in acetone! Acetone react with solid of iodium and added by aquades. Then it shaked and finally added by NaOH solution. 5. Test the solubility of iodoform in water! Is the water can be used as a solvent for recrystallization iodoform? Explain! Iodoform cannt dissolve either in cold nor hot water, so it cannt be used as a solvent for recrystallization iodoform. 6. Calculate precentage of iodoform that you get! Calculation:

Reaction: 3I2 Initial: React: Rest : 0,00328 mol 0,03086 mol + CH3COCH3 CH3COCI3 + 3HI 0,00328mol 0,00328mol -

CH3COCH3 + NaOH Initial: React: Rest: 0,03086 mol mol 0,01186 mol mol mol -

CHI3 -

CH3COONa -

mol mol

mol mol

7. Write the equation of ethyl acetate, propanol, methanol, n- buthyl alcohol, secbuthyl alcohol,4-methyl-2-pentanol, dan 2-pentanon. Are those subtances positive in testing iodoform?

8.

Where is the possible failure of the preparation of iodoform? a. Failure can occur if the condition is too alkaline b. The reaction between acetone and iodine deficient, which is not all form iodoform. c. Weighing improper.