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These are notes and practice questions on chapter 11 of the student's book of IGCSE Chemistry. This will give you a clear understanding on the concept of making salts for example details on precipi...
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organic experiment report
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organic experiment reportFull description
Lecture by: Do Dot Dotsha tsh sha a J. Raheem Assistant Lecturer Department of Chemistry College of Science University of of Salahadin 2010
Week (1): Nitration of Acetanilide Acetanilide
1.
Preparation of Acetanilide O O
NH2
O
H3C + H3C Aniline
HN
O O
CH3
CH3
Acetic anhydride
O
OH + Acetanilide
H3C
OH
Acetic acid
2.
Nitration of o f Acetanilide O
HN
O
O CH3
HN HNO3 / H2SO4
HN
CH3 NO2
CH3
+ NO2
Acetanilide o-nitroacetanilide
p-nitroacetanilide "Major product"
3.
Hydrolysis of Acetanilide H
H
1) Hydrolysis
H
H ,H ) -nitroacetanilide
H -nitroaniline
Acetanilide Importance of Acetanilide m-director o,p-director
NH3
NH2 +
HNO3 H2SO4
HNO3 / H2SO4 Anilinium ion
Aniline
So, acetylation protects aniline from protonation, charring and oxidation
Charring and oxidation of aniline
meta substitution
This
lab.:
/
c ta i li - itr ac ta ili
- i tr ac ta il i " a r r ct"
Q/
The
major product is para, but why not ortho?
This
is mainly due to steric effect.
ortho-nitroacetanilide
para-nitroacetanilide
ortho-nitroacetanilide
para-nitroacetanilide
Notes on the Experiment
Nitration of acetanilide is an exothermic reaction ; the temperature must be carefully controlled by chilling, stirring, and the slow addition of reagents. The
reaction is conducted below 0Û C to maintain selectivity by preventing less favorabl favorable e reactions reactions from occurri occurring ng [o[o- and 2,42,4dinitro products require higher energy]
Notes on the Experiment
Glacial acetic acid is used because it is a polar solvent capable of dissolving acetanilide, and the acetate ion is a poor nucleophile so no substitution is possible. A mixture of concentrated nitric and sulfuric acids is used as the nitrating mixture.
Notes on the Experiment
To
prev prevent ent dinitr dinitrati ation on of the the acetan acetanili ilide, de, the nitrating mixture is added in small portions to the acetanilide solution (and not vice versa) so that the concentration of HNO3 is kept at a minimum. After the addition is complete the beaker is allowed to stand at room temperature for 30 minutes [more than that will lead to the formation of 2,4-dinitroacetanilide].
Notes on the Experiment
o-nitroacetanilide has higher solubility in the aqueous solution than p-nitroacetanilide.