Experiment 1: Synthesis of Acetamides from Aniline and Substituted PDF

SUPPORTING INFORMATION

Optimisation of the reaction temperature for the acetylation of aniline derivatives. Investigations into the reaction mechanism using 3-phenylpropionic acid ...

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A mechanism was proposed for the catalysed reaction between aniline and the general acid catalyzed migrations of acetyl and benzoyl groups shown in ...

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A Convenient Laboratory Preparation of Acetanilide*. Preparation of acetanilide by the acetylation of aniline is an important exercise in organic synthesis

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quantity of aniline hydrochloride in the presence of aniline as solvent (i) Why is acetic anhydride preferred over acetyl chloride for acetylation reaction?

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The re- actions of acetyl phosphate at neutral pH. with hydroxylamine aniline

Experiment 14 Preparation of p-Nitroaniline

Figure 14.2 Mechanism of Acetylation Reaction. H2N aniline. +. CH3. C. O. C. CH3. O. O. NH C. O. CH3. +. O. C. CH3. O acetanilide acetic anhydride acetic acid.

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acetylation of aniline by aryl acetate ([aniline] = 6.62 x ... acetanilide .in reaction 6 in the absence of the catalytic mechanism involving the intermediate.

Experiment 1: Synthesis of Acetamides from Aniline and Substituted

03-May-2011 Experiment 1: Synthesis of Acetamides from Aniline and ... Acetylation of aniline ... Additional comments on the reaction mechanism:.

Experiment 14 Preparation of p-Nitroaniline

nitroaniline from aniline and then we will characterize our product using the new and Figure 14.2 Mechanism of Acetylation Reaction. H2N aniline.

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Reaction:N-acylation / N-acetylation / Electrophilic Substitution Reaction. Chemicals: Aniline - 5mL. Glacial acetic acid - 5mL. Acetic anhydride - 5mL.

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Aniline. : 5 mL. • Acetic anhydride. /Acetyl chloride (iii) Cool the reaction mixture and pour it slowly in 150-200 mL of ice cold water with stirring.

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Scheme SM 3.1.5.1 – General acetylation reaction mechanism of an alcohol with acetic The reaction between maleic anhydride and the aniline (aniline ...

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The re- actions of acetyl phosphate at neutral pH. with hydroxylamine aniline

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Chem 216 S11 Notes - Dr. Masato Koreeda Date: May 3, 2011 Topic: __Experiment 1____ page 1 of 2. Experiment 1: Synthesis of Acetamides from Aniline and Substituted Anilines Many of the acetylated [CH3-C(=O)-] derivatives of aromatic amines (aka anilines) and phenols are pharmacologically important compounds. Some of these exhibit distinct analgesic activity. Two of the most representative examples are: H

NCH 3 O acetaminophen (Tylenol) HO OCH 3 O OHO acetylsalicylic acid (Aspirin)

======================================================================= The reaction to be carried out in this experiment is: Acetylation of aniline HN

H aniline (nucleophile) CH 3 O O O H 3 C acetic anhydride (electrophile) H NCH 3 O acetanilide CH 3 HOO acetic acid

Both aniline and acetic anhydride are somewhat viscous liquids. So, simply mixing them together does not result in the efficient formation of acetanilide. Therefore, a solvent (in this case water) is used to dissolve and evenly disperse two reactants in it. R'

NR" O R CH 3 O acetyl group Note: R' NCH 3 O R amide acetamide R' N R" O R

The amide N is usually not nucleophilic

because of a significant contribution of this resonance form.

Reaction mechanism: N

CH 3 O H 3 C O O HH N CH 3 OO O H 3 C H H tetrahedral (sp 3 ) intermediate N O CH 3 H H OCH 3 O

B(including

OCH 3 O pK a ~ -5 NCH 3 O H acetanilide

Chem 216 S11 Notes - Dr. Masato Koreeda Date: May 3, 2011 Topic: __Experiment 1____ page 2 of 2. Additional comments on the reaction mechanism: 1. Aniline is a strong nucleophile (much stronger than water). 2. Acetic anhydride is a relatively unstable reagent, but does not react with water that easily. 3. N

CH 3 O H 3 C O O HH A direct substitution process at the C=O carbon does not take place.

No direct S

2 reaction at the C=O carbon is known. This is not feasible

on the basis of the orbital consideration.

Experimental procedure: Aniline is not soluble in water; so 1 mol. equiv of conc. HCl (37% HCl by weight in water) is added in order to dissolve the aniline in water. aniline

H 2 O

Erlenmeyer flask

Don't use a beaker!

H 2 O PhNH 3 Cl (all dissolved) add 1 mol equiv of conc HCl homogeneous solution H 2 O H 2 O

Mostly PhNH

3 and NaCl, acetic anhydride, and CH 3

C(=O)O

(dissolved in H 2 O) add 1 mol equiv of acetic anhydride PhNH 3 Cl acetic anhydride (still all dissolved in H 2 O) no reaction yet! H 3 CO Na O add 1.2 mol equiv of (sodium acetate) - weak base

By the action of sodium acetate,

a small amount of free aniline (PhNH 2 is regenrated.

Free aniline has virtually no water solubility.

But before aniline comes out of the H

O solution,

it quickly collides (i.e., reacts) with acetic anhydride dissolved in H 2

O. As soon as the

acetamide product (acetanilide) is formed, it will precipitate out of the H 2

O solution and

more PhNH 3 gets converted to free aniline.... acetanilide as white precipitates (collect by suction filtration)

NaCl, acetic acid and

CH 3

C(=O)O

dissolved in H 2 O o o o o oo o o o o o o o o oo o o

Questions: (1) What would happen if the order of additions of acetic anhydride and sodium acetate is reversed? (2) What would be the outcome if 1 mol equiv of NaOH is used instead of sodium acetate? (3) What would you have to do in order to dissolve p-nitroaniline into water by adding conc. HCl? The pKa of the conjugate acid of p-nitroaniline is 1.00 (see the note on pKa).

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[PDF] Experiment 1: Synthesis of Acetamides from Aniline and Substituted

The amide N is usually not nucleophilic

Reaction mechanism: N

B(including

No direct S

2 reaction at the C=O carbon is known. This is not feasible

Erlenmeyer flask

Don't use a beaker!

Mostly PhNH

C(=O)O

By the action of sodium acetate,

Free aniline has virtually no water solubility.

But before aniline comes out of the H

O solution,

O. As soon as the

O solution and

NaCl, acetic acid and

C(=O)O