week 7-9 carboxylic acids preparation of methyl 3 ... of methyl benzoate = 2.1 ml x 1.09 g/ml = 2.29...

Week 7-9 Carboxylic Acids Preparation of Methyl 3-Nitrobenzoate Preparation of 3-Nitrobenzoic Acid Preparation of 3-Nitrobenzamide

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Week 7-9 Carboxylic Acids

Preparation of Methyl 3-Nitrobenzoate

Preparation of 3-Nitrobenzoic Acid

Preparation of 3-Nitrobenzamide

Page 2: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

Preparation of 3-Nitrobenzoic Acid

CO2CH3

NO2

1. NaOH, heat

2, HCl

CO2H

NO2

Page 3: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

Preparation of 3-Nitrobenzoic Acid Basic Hydrolysis Mechanism

(Saponification)

Page 4: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

Saponification Hydrolysis of Triglycerides

Page 5: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

- 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.

!!!!!!!!!- NaOH is VERY hydroscopic and a very strong base

(DON’T TOUCH IT with bare hands) !

Overall….

CO2CH3

NO2

1. NaOH, heat

2, HCl

CO2H

NO21 g

0.7 g

2 mL

2.2 gX

2.2 x 0.7 g

2.2 x 2 mL

Page 6: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

Preparation of 3-Nitrobenzoic Acid Procedure

!Weigh NaOH in a beaker!

Mix ester + water + NaOH

50 mL

!Heat over steam bath with CONTINUOUS SWIRLING

until all crystals have melted and the solution turns pale

yellow.

After the solution is transparent / pale yellow keep heating for 5 more

minutes for the reaction to be completed.

Page 7: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

Preparation of 3-Nitrobenzoic Acid Procedure

Dilute the solution with an equal

volume of water

Add the diluted solution to a beaker containing 2 ml of concentrated HCl, while stirring.

Ice bath

Vacuum Filtration

Dry filter spread solid on

watch glass

Page 8: Week 7-9 Carboxylic Acids Preparation of Methyl 3 ... of methyl benzoate = 2.1 mL x 1.09 g/mL = 2.29 g How many moles are there in 7.5 mL of concentrated sulfuric acid? M of concentrated

Calculating Moles of Compounds

1. If a Solid

Mole =g of Compound

Molecular weight

2. If a Liquid

Molarity (M) =Moles

Liter

Mole = M x Liter

Also:

Density (d) =Mass

Volume=

grams

Mass = mL x d

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

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

M of concentrated Sufuric acid =Moles of sufuric acid

0.0075 L= 18

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

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