Lab Book Organic Chemisty

Topics: Chemistry, Amine, Functional group Pages: 7 (711 words) Published: September 25, 2013

CHM1002

Synthesis of Benzanilide and Methyl 3-Nitrobenzoate and the Identification of ‘Unknowns’ from Spectroscopic and Physical Properties

James Lucas
10394308

23/11/12

Introduction
In this series of practicals it was the aim to synthesise both Benzanilide and Methyl 3-Nitrobenzoate. Benzanilide was synthesised using The Schotten Baumann reaction which takes a hydrogen atom from an amino group and substitutes it for an acyl group. For Methyl 3-Nitrobenzoate, NO2+ was used as an electrophilic reagent to replace an aromatic hydrogen atom. Then both chemicals were purified by first determining appropriate recrystallisation solvent, before analysing Benzanilide and Methyl 3-Nitrobenzoate as well as 2 unknown compounds (B & E) using melting point determination and IR spectrometry to find the purity. Procedure

For method used please refer to CHM1002 Stage 1 Organic Chemistry Practicals Term 1 lab script. Only deviation was that, the use of Decolourising Carbon and Filtration of the hot solution was skipped in this set of practicals

Results

Determination of an appropriate Recrystallisation Solvent
0.02g of crude solid in each test tube. 0.5 cm3 (initially) of solvent in each test tube

Solute: Benzanilide
Solute: Methyl 3-Nitrobenzoate
Solvent
Soluble at 0.5cm3
Soluble at 1.0cm3
Soluble when heated
Recryst-allised

Solvent
Soluble at 0.5 cm3
Soluble at 1.0 cm3
Soluble when heated
Recryst-allised

Methanol
Negative
Negative
Negative
Negative
Methanol
Negative
Negative
Negative
Negative
Ethanol
Negative
Negative
Positive
Positive
Ethanol
Negative
Negative
Negative
Negative
Toluene
Negative
Negative
Positive
Positive
Toluene
Negative
Negative
Negative
Negative
Petroleum Ether
Negative
Negative
Negative
Negative
Petroleum Ether
Negative
Negative
Positive
Positive
Water
Negative
Negative
Negative
Negative
Water
Negative
Negative
Negative
Negative
Solvent used = Ethanol because from Solvent used = Petroleum Ether COSHH assessment it is shown as
being safer than Toluene
After dissolving the product – left to stand for 10-15mins

Melting Points

Compound
Melting Point oC Rough
Melting Point oC #1
Melting Point oC #2
Melting Point oC #3
B
79
79.4
79.3
79.6
E
107
106.8
107.1
107.2
Benzanilide
162
161.7
162.2
163.4
Methyl 3-Nitrobenzoate
77
77.6
77.3
76.8

Selective Reduction Reactions
Compound
Nitro group test
Aromatic amine
Carbonyl Group
Alcoholic Hydroxide
B
Positive
Negative
Positive
Negative
Positive
E
Negative
Positive
Positive
Negative
Negative
Benzanilide
Negative
Positive
Positive
Negative
Negative
Methyl 3-Nitrobenzoate
Positive
Negative
Positive
Negative
Negative

Compound B contains: Nitro group, carbonyl group
Therefore must be either 1-(3-nitrophenyl) ethanoate or 1-(4-nitrophenyl) ethanoate

Compound E contains: Aromatic Amine group, carbonyl group
Therefore must be either 1-(3-aminophenyl) ethanoate or 1-(4-aminophenyl) ethanoate

IR Spectra

Figures 1,2,3,4 – IR Spectrums Relating to Sample B (1), Sample E(2), Methyl 3-Nitrobenzoate(3) and Benzanilide(4)

Discussion
Compound
Literature Melting Points oC
1
78
2
57.59
3
98
4
79
5
N/A
6
107
By looking at the melting points for B & E and comparing them to the literature values, it is possible to narrow the structure of both unknown compounds down from the suggest compounds in the results section (1-(3-nitrophenyl)ethanoate) or 1-(4-nitrophenyl)ethanoate) for compound B and (1-(3-aminophenyl)ethanoate or 1-(4-aminophenyl)ethanoate) for compound E.

Compound
Mean Melting Point oC
B
79.4
E
107.0

From comparison of the two data tables it can seen
that Compound E has the same melting point as
compound 6, which is 1-(4-aminophenyl)ethanoate.
However for...

References: First Year Spectra Collection 2012, University of Plymouth
CHM1002 Stage 1 Organic Chemistry Practicals Term 1 Lab Script 2012, University of Plymouth
Clayden, J., Greeves, N., Warren, S. and Wothers, P. (2001) Organic Chemistry, Oxford University Press.
http://www.chemistry.ccsu.edu/glagovich/teaching/316/ir/table.html (accessed 18/11/12
Continue Reading

Please join StudyMode to read the full document

You May Also Find These Documents Helpful

  • Organic Lab Report Essay
  • Organic Lab Essay
  • Organic Lab 7 Essay
  • sample lab reoort on purification and separation of organic compounds Essay
  • Essay about Organic 2 Lab Report- Aldehydes & Ketones: Finding an Unknown
  • Writing an Organic Chemistry Lab Report Essay
  • organic Essay
  • organic chemistry lab manual Essay

Become a StudyMode Member

Sign Up - It's Free
Kelcy Griffin | Clique - Saison 2 (Ajout de l'Episode : 3) (HDTV) | Grisse HDTV 720p AC3 5.1