Experiment 1: Preparation of Benzamide

General Mechanism-Nucleophilic Acyl Substitution

O
O O

C + :Nu C C + :Y
R [1] R [2] R Nu
Y Nu
Y
Tetrahedral carbonyl Substitution
addition intermediate product

Nucleophilic attack
Loss of a leaving Group

In Step [1]: the nucleophilic attack the carbonyl group cleaving the π bond and forming a
tetrahedral intermediate with a new C-Nu bond
In Step [2] elimination of the leaving group forms the substitution product.
 Characteristic Reactions
Poor bases make good leaving groups.
O
R2 N- RO- RCO- X-
Increasing leaving ability
Increasing basicity

Halide ion is the weakest base and the best leaving group;
acid halides are the most reactive toward nucleophilic
acyl substitution.
Amide ion is the strongest base and the poorest leaving
group; amides are the least reactive toward nucleophilic
acyl substitution.
 Acid amide having relatively high boiling points

Amides have the

highest boiling
points

B.P of Acetic acid is 118 ◦C

B.P of Acetamide is 221 ◦C

Synthesis of Benzamide
Possible Mechanism of Benzamide Formation

Benzoyl Chloride Tetrahedral Intermediate

Benzamide
 Procedure for Benzamide Preparation

1. 1.3 mL of Benzoyl chloride into a small dry test tube.

2. Test tube Cool to room temperature
3. 4 mL of aqueous ammonia will add to the test tube dropwise manner
4. Reaction mixture will mixed well the wall of the tube will scratching to prevent solidification
of the ppt.
5.Filtrate the reaction mixture by using what-man filter paper and cold water
6.Buchner filtrate the Benzamide and wash thoroughly with ice cold water. and re-crystallise from
hot water (5 ml)
7.The crystal solids should be dried and put in oven for 10 mins
8.Then weight the product and will take melting point
Buchner filtration
 Risk Assessment

• Benzoyl Chloride is corrosive and causes burns to the skin.

• Benzoyl Chloride vapours cause severe irritation to eyes

• Aqueous ammonia is poisonous and corrosive

• Wear gloves, lab coats and safety glasses.
• Inform INSTRUCTORS/TA immediately if somethings gets on your skin.
 Recrystallization of Benzamide
The Experimental Process:

1.Find a suitable recrystallization solvent for your solid

(solute) - solubility; refer to Table 4.1
• First try hexanes (nonpolar), if needed try water (polar)
• Trial and error
• Choice of solvent will give a clue as to the type of
compound you have - either nonpolar or polar
• Ideal solvent: solute insoluble at rt, solute soluble with
heat

2.Dissolve the compound in a minimal amount of the chosen

solvent

3.Remove insoluble impurities (may skip)

• Pipet Filtration, hot filtration

4.Crystallize your compound - slow cooling of crystals;

5.Collect and wash the crystals
• Pipet filtration or vacuum filtration
6.Dry the crystals
 Calculations
Tabulation:
S.No Molecular Equivalent Milimol Density(g/ Amount
  Wt. ml)
 
Benzoyl chloride 140.57 1 11.19 1.21 1.573
NH3 17 Excess Excess    

Calculation:
Volume of the Benzyl chloride= 2 ml
Density of Benzyl Chloride=1.21 g/ml
Density=(Mass/Volume)
Mass= Density. Volume= 2*1.21= X gm
Molecular weight of Starting materil= 140.57
M.Wt of benzamide= 121.14 gm
Theritical yield= 121.14/140.57* X= Ygm
% Yield: Experimental yield/Theoritical yield * 100= Z %

Melting Point:
Thank You