Experiment Report

Identifying the unknown carbonyl compound

By Kelvin Timotius and Manoel Manuputty (Brilliant Class Year 11 SMAK PENABUR Gading Serpong)
Introduction
There are some main types of functional group in Chemical compounds. Functional Group is a part of chemical compound which determine chemical and physical properties of the compound. One of the most famous functional group in chemical compound is the carbonyl group. We may be often meet any carbonyl compounds around us without recognize it, such as nail polish, formalin, glue, etc. To find out the way to recognize a carbonyl compound, we have to determine some special properties of the compound and design a method to test it. Carbonyl group consists of two sub-funtional groups, there are aldehyde and ketone. Basically, Aldehyde and Ketone have some different properties. The most basic difference between Aldehyde and Ketone groups is their ability to be oxidized by few chemical reagents. Some oxidizers such as potassium dichromate (VI), potassium manganate (VI), fehling reagent, and tollens reagent ([Ag(NH3)2]OH) can be used as indicator for testing aldehydes because they can oxidize the compound and give change in color and precipitate while they do not give any change after treating with ketones. Furthermore, there is another method to determine structure of carbonyl compound by testing it with Iod (I2) in alkaline condition by adding NaOH (Sodium Hydroxide) which called Iodoform test. Iodoform test is used to test methyl group in carbonyl or alcohols compound.

Objectives
The goal of the experiment is to identify an unknown solution called solution X with some information and different methods, also to learn about aldehyde and ketone tests (tollens and fehling).

Methods
From recent experiment, we knew that solution X cannot be oxidized, it also does not react with iodoform test. What we did in this experiment was to determine whether the solution X is a ketone or an aldehyde. So, in order to learn about the solution more, we did tollens and fehling tests. We also compared the results of the tollens and fehling tests of the solution X with those of the aldehyde (in this case formaldehyde).

Identifying the unknown carbonyl compound

Tollens Test
Clean two test tubes with sodium hydroxide, and then wash them. Add 2.5ml of silver nitrate 5% to each of the tube then add ammonia drop by drop until there is no precipitate. Add 1 drop of sodium hydroxide 10%, if there is precipitate then add ammonia until no more precipitate. Add 5ml of solution X to one of the tube, and 5ml of formaldehyde to the other. Heat the tubes!

Fehling Test
Clean three test tubes with sodium hydroxide, and then wash them. Add 1 ml of fehling A and 1 ml of fehling B to one of the tubes, mix them. Drop 1 ml of the fehling mixture to each of the tube (currently two tubes). Add 5ml of solution X to one of the tube, and 5ml of formaldehyde to the other. Heat the tubes!

Results
Identify Compound X
Compound X has boiling points about 56.5C. Weve done four tests on solution X: oxidation, fehling, tollens, and iodoform. Which result as: OXIDATION NEGATIVE No Change TOLLENS NEGATIVE No Change FEHLING NEGATIVE No Change IODOFORM POSITIVE Yellow precipitate

From the boiling point information and result above, we can conclude that: 1. Compound X has neither alcohol nor aldehyde group (cant be oxidized) 2. Compound X has methyl group besides ketone group (iodoform test) 3. Compound X has relatively low boiling points which we can say that it has relatively short carbon chains and is a nonpolar/semipolar compound. For a comparison ethanol which has two carbon chains and is a polar molecule has boiling points about 78C. Since the probability only lead us to ketone group (acetone, buthan-2-on, etc), we could conclude that the compound X is acetone (CH3COCH3), because ketones with longer carbon chains will have higher boiling points than ethanol which are incorrect. Brilliant Class, BPK Penabur | [Kelvin and Noel]

Identifying the unknown carbonyl compound

Fehling and Tollens Tests

From the fehling and tollens test which are tests to differ aldehydes and ketones, we know that compound X is not an aldehyde since it was not react with tollens and fehling (no change happen). But, how about the formaldehyde? The formaldehyde reacted with both fehling and tollens. Which result as: FEHLING Red-Brown Precipitate TOLLENS Silver mirror in the test tube

Discussion
Q : What is main chemical property which explain ability of aldehyde compound to be oxidized while ketone is not? A : Aldehyde compound has a Hydrogen carbonyl which is able to oxidized, while ketone has no one and it makes ketone is not able to oxidized.

Q : What happens when an aldehyde give silver mirror when treated with tollens reagent and give red-brown precipitate when treated with fehling solution? A : When the aldehyde compound treated with tollens reagent, the following chemical reaction occurs:

We could see that the reaction yields Silver precipitate (silver mirror). When aldehyde treated with Fehling solution, the following chemical reaction occurs:

In this case, Cu2O is a red-brown precipitate.

Q : What is the difference between Fehling A and Fehling B? A : Fehling A is a solution of Copper (II) Sulfate pentahydrate (69.28 grams in 1 L of water), while fehling B is a solution of Rochelle salts (Potassium Sodium tartrate tetrahydrate) and Sodium Hydroxide (NaOH) in distilled water (346 grams of Rochelle salt, 120 grams of NaOH, and 1 L water)

Q : Why do we have to heat the tubes?

Brilliant Class, BPK Penabur | [Kelvin and Noel]

Identifying the unknown carbonyl compound

A : Heating tubes was intended to accelerate the reaction between solutions and reagents, especially for fehling test because it will need much more time to react when not heated.

Q : How can we conclude that low boiling point of the unknown compound means that the compound has relatively low molar mass or the compound is a non-polar or semipolar compound? A : Boiling point is affected by intermolecular forces in one compound. When a compound has low boiling point, it means that the intermolecular forces is also low. A polar compound, usually has high boiling point because the compound has dipole force between it molecules and make it strong. Thats why we can conclude that the compound is a non-polar or semipolar compound. Relatively low molar mass is also affect the low boiling point.

Q : Why cant we conclude that the compound was ethanol since we know that methyl alcohol is also give positive result when treated with iodoform test? A : Although ethanol is also give positive result when treated with iodoform test, but we know that the unknown compound does not give positive result when oxidized which means that it is not ethanol since we know that ethanol is easily oxidized to form acetic acid.

Conclusion
After some chemical tests and compared with informations given, we could conclude that the compound X is acetone, which is a carbonyl compound especially ketone group.

References
http://en.wikipedia.org (accessed : February 3rd 2009) http://www.google.co.id (accessed: February 3rd 2009)

FEEDBACK
INTRODUCTION = introduction sudah bagus, hanya pengunaan SUBJECT biasanya dilarang, karena report itu bersifat universal. Tetapi ini kembali kepada kebijakan dosen dan kampus. Pada dasarnya, report yang baik adalah report yang bersifat universal. OBJECTIVES =Padat, singkat, jelas. PERFECT METHODS = Padat, singkat, jelas.PERFECT RESULTS = Penyajian data sudah bagus dan dapat dimengerti DISCUSSION = Diskusi experiment sudah detail dan sangat jelas CONCLUSION = Padat , singkat , jelas. PERFECT

Brilliant Class, BPK Penabur | [Kelvin and Noel]

Identifying the unknown carbonyl compound

REFERENCES = references juga sudah bagus, karena cara penulisan references tergantung sama kebijakan sekolah/kampus, jadi dalam penulisannya boleh dengan format apa aja selama itu masih berlagu ( e.g. Chicago Referencing, Harvard Referencing )

Please note: 1. Pengunaan SUBJECT kalau bisa dihindari. Bersifatlah universal

2. Sebagai saran dan masukan, WIKIPEDIA biasanya jarang dipake sebagai referensi. Memang ada beberapa dosen yang suka dan ada yang ga suka, jadi tergantung sama kebijakan kampus dan dosennya ;)

Brilliant Class, BPK Penabur | [Kelvin and Noel]