Ixtlahuaca University CUI

Lic. En Qumico Farmacetico Bilogo

Pre Report
LABORATORY SYNTHESIS OF COMPOUNDS HETEROCYCLIC

Practice #1
PAAL - KNORR REACTION: OBTAINING PYRROLES

Team #3

Members:
Mendoza Jose Manuel Paz Mendoza Jorge Luis Quezada Nuez Ivan Cirilo Ramirez Mayra Yunuen Reyes ramos jaqueline
Date of practice:
5th September 2013

OBJETIVES

The student should obtain a heterocyclic compound of five members from the Paal - Knorr reaction by condensation of dicarbonyl compounds and aniline Identify and explain each of the steps of the methodology of the practices of obtaining such compounds To obtain the 1-phenyl- 2 ,5- dimethylpyrrole through a condensation reaction between aniline and dicarbonyl uncompuesto (or derivatives thereof ) .

HYPOTHESIS Verify obtaining a pyrrole compound from Pall- Knorr reaction, and to determine the reaction yield and the factors that may affect the performance and results of the practice.

RESULTS

She started placing hexanedione and aniline hydrochloride which took a gray color.

By adding ethanol was formed light brown; was armed reflux where its initial temperature was 50 C.

Once reflux was observed started changing colors. The first change was in 10 min light brown to brown.

The next color change was in 13 min where it was observed that this became more obscure.

Then the last change was in 27 min, the color was more intense (red blood).

Finally, filter, scrape the solid by adding ethanol to purify the substance and heated.

DISCUSSION OF RESULTS This practice was carried out using 2, 5 -hexanedione , aniline hydrochloride . By the reflux method using ethanol as a solvent, wherein the heat applying means functions as an acid catalyst. During the reflux period, we observed a change of tone colors from light brown to blood red. We performed a recrystallization using ethanol as solvent for purifying the product obtained. Where the product obtained was a solid light cream, almost white which is characteristic of the pyrrole. CONTRAST WITH THE HYPOTHESIS Through research literature is found that the Pall- Knorr reaction this being a method of organic synthesis which furans originally obtained from 1,4 -diketones and their use spread synthesis of pyrroles and thiophenes initially reported independently by German chemists and Ludwig Carl Paal Knorr the Paal - Knorr synthesis has been widely used , while the procedure is observed that the main factors of error is mostly obtained in the measurement reagent when preparing the solution , note that the use of inappropriate equipment also influences obtaining erroneous data , an important part during practice is to be consistent

with the procedure and that disruption of this can cause even more errors in performance of our product. CONCLUSIONS During this practice job with a 5-membered heterocyclic pyrrole molecule called flat with bond angles of 120 found in small amounts in coal tar , as well as in bones and other products derived from proteins and their main reaction Pall- Knorr synthesis , was analyzed likewise said synthesis mechanism , as in previous practice and knowledge this is reinforced by literature research also strict care reagent handling , the team analyzed in this type of practice is important not to interrupt or change the literal process this order only to get the results marked as by modifying reagents or measuring percent of these data often change, this to avoid not having a standard which the team can guide and verify the data. QUESTIONS

QUESTIONNAIRE 1. - What is the mechanism of the transformation of 2,5- hexanedione and aniline to form the corresponding pyrrole ?

2. - What is the function of hydrochloric acid in the reaction ? R = Used as a reaction catalyst to hydrolyze the 2,5 -hexanedione and form the compound which can react with the amine of the aniline 3. - In the acidification of water composite is being removed ? R = hydroxy are renewed up to 2.5 dihidroxitetrahidrofurano 4. - Draw the chemical shift and the doubling of signals in the spectrum of H- NMR of the product.

The CH have shaped singlet signal because it has more hydrogen neighbors.

These signals are those of the aromatic hydrogens.

5. - What are the raw materials for making only 2 - methylpyrrole ? Require the presence of 2,5 -hexanedione and aniline amine contained no acid medium