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ATR-FTIR spectra of non-crystalline and crystalline solid

of 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
(MNYAD_1539)
Nurin Zarifah1, Nur Najihah,,
M. Rashidi Abdull Manap1,2 Tasnim Munshi2, Ian J. Scowen2
1Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
2School of Chemistry, University of Lincoln, Joseph Banks Laboratories, Green Lane, Lincoln, Lincolnshire, LN6 7DL, UK

Corresponding email; atiradriana@gmail.com

ABSTRACT RESULTS AND DISCUSSION


An aldol condensation is a condensation reaction in organic Base catalysed Aldol condensation of MNYAD_1539:
chemistry in which an enol or an enolate ion reacts with a
carbonyl compound to form a β-hydroxyaldehyde or β-
NaOH
hydroxyketone, followed by dehydration to give a conjugated
enone. In the aldol condensation reactions which reaction of
aromatic aldehydes with acetonphenone and ethanol. The title H2O
compound, 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one was
synthesized in high yield by aldol condensation of p-methoxy non-crystalline solid sample
benzaldehyde and acetophenone in ethanolic NaOH. Its structure
was characterized by IR analysis.

INTRODUCTION
Aldol condensation is a reaction that is named based on the
type of product formed when two aldehydes or ketones, in the
presence of dilute base, yields a molecule having both alcohol
and aldehyde functional groups. A base catalyzed Aldol
reaction has been performed and dehydration- an elimination
Figure 2: non crystalline yellow solid from Aldol condensation reaction. Its
reaction to remove water molecule- turned the Aldol to yellow crystalline sample has needle-like shape under the microscope.
Aldehyde. The product is a β-Hydroxy-Aldehyde or a β-
Hydroxy-Ketone. The product results from the addition of one FTIR analysis:
molecule of an aldehyde (or ketone) to a second molecule in
such a way that the α-carbon of the first becomes attached to
the carbonyl carbon of the second.
(a)

(b)

Figure 3: Solid state ATR-IR spectra of 3-(4-methoxyphenyl)-1-phenylprop-2-


Figure 1 : Chemical structure of MNYAD_1539 en-1-one. (a) non crystalline sample (b) crystalline sample. Peak positions for
both samples are consistent but there are slight differences in the
METHODOLOGY Transmittance values. The spectrum of non crystalline sample and 3-(4-
methoxyphenyl)-1-phenylprop-2-en-1-one (MNYAD_1539) is comparable.

p-methoxy benzaldehyde + acetophenone


+ ethanol + NaOH

Add cool distilled water Put in the ice water bath

Put in the ice water bath Add cool distilled water

Figure 4: The presence of water in the non crystalline sample led to a broad
Filter Off signal in region above 3000 cm-1 that was readily distinguishable from that of
crystalline sample. However, a weak signal at 3310 cm-1 is not affected.

Recall back, based on the methodology steps, there are a few of different steps occurred in the preparation of p-
methoxybenzalacetophenone, which leads the different formation of product at the end of the experiment such as the product is in the
powdered form, not the crystal one.

From here, it can be concluded that a non-prefect removal of water from the product might resulting the formation of powdered p-
Recrystallize methoxybenzalacetophenone.

Powder Crystal
3-(4-methoxyphenyl)-1- 3-(4-methoxyphenyl)-1-
phenylprop-2-en-1-one phenylprop-2-en-1-one

REFERENCES
CONCLUSIONS: 1. Nielsen, Arnold T., and William J. Houlihan. "The aldol condensation." Organic reactions (1968).

1. Product formed in powdered form not in crystal form due to different methodology 2. “AldolCondensation”(2018).Retrievedform

used why conducting the experiment. https://chem.libretexts.org/Core/Organic_Chemistry/Reactions/Organic_Reactions/Aldol_Condensation.

3. Retrieved from https://www-sciencedirect-


2. The formation of powder is due to non-perfect removing water from the product.
com.proxy.library.lincoln.ac.uk/science/article/pii/S0379677916300169#fig0015
3. The different in trend if compared the red and blue spectra is due to the presence
4. Retrieved from https://www-sciencedirect-com.proxy.library.lincoln.ac.uk/science/article/pii/S1386142517306868
too much of water in the product obtained (blue spectra).