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Experiment 8

The document describes the preparation of 3-nitrobenzoic acid from methyl 3-nitrobenzoate. It involves basic hydrolysis of the ester using sodium hydroxide to yield 3-nitrobenzoic acid. The procedure is provided along with notes on adjusting amounts based on the amount of starting ester available and safety precautions for handling sodium hydroxide.

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Benson Shayo
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23 views8 pages

Experiment 8

The document describes the preparation of 3-nitrobenzoic acid from methyl 3-nitrobenzoate. It involves basic hydrolysis of the ester using sodium hydroxide to yield 3-nitrobenzoic acid. The procedure is provided along with notes on adjusting amounts based on the amount of starting ester available and safety precautions for handling sodium hydroxide.

Uploaded by

Benson Shayo
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Week 7-9
 
Carboxylic Acids

 
Preparation of Methyl 3-Nitrobenzoate

 
Preparation of 3-Nitrobenzoic Acid

 
Preparation of 3-Nitrobenzamide
Preparation of 3-Nitrobenzoic Acid

CO2CH 3 CO2H
1. NaOH, heat

2, HCl
NO 2 NO 2
Preparation of 3-Nitrobenzoic Acid
Basic Hydrolysis Mechanism
(Saponification)
Saponification
Hydrolysis of Triglycerides
Overall….

- Get the methyl 3-nitrobenzoate you made last time.


- Keep a small amount to take mp.
- Use the rest of your ester to set up the next reaction.
The procedure in the manual is written for 1 g of ester.
You will NEED to ADJUST the amounts to correspond to
your amount of ester.
!
!
CO2CH 3 X
0.7 g 2.2 x 0.7 g CO2H
! 1. NaOH, heat
!
2, HCl
!
!
NO 2
X
2 mL 2.2 x 2 mL NO 2
! X
1g
! 2.2 g
!
- NaOH is VERY hydroscopic and a very strong base
(DON’T TOUCH IT with bare hands)
!
Preparation of 3-Nitrobenzoic Acid
Procedure
!
Weigh NaOH
in a beaker!

50 mL
!
Heat over steam bath with After the solution is
CONTINUOUS SWIRLING transparent / pale yellow
until all crystals have melted keep heating for 5 more
and the solution turns pale minutes for the reaction to be
Mix ester +
yellow. completed.
water + NaOH
Preparation of 3-Nitrobenzoic Acid
Procedure
!

spread solid on
watch glass Dry filter

Dilute the solution


with an equal
volume of water Vacuum
Filtration

Ice bath

Add the diluted solution to a beaker containing 2 ml


of concentrated HCl, while stirring.
Calculating Moles of Compounds

1. If a Solid

g of Compound
Mole =
Molecular weight

2. If a Liquid

Moles
Molarity (M) =
Liter

Mole = M x Liter

How many moles are there in 7.5 mL of concentrated sulfuric acid?

Moles of sufuric acid


M of concentrated Sufuric acid = = 18
0.0075 L

Moles of sulfuric acid = 18 moles/L x 0.0075 L = 0.135 moles

Also:
Mass grams
Density (d) = =
Volume mL

Mass = mL x d

mass of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g  

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