l in the Substance Mass (g) MW (g/mol) Mmol Equivalents Sulfanilic acid 6.417329 173.2 0.1 1 2-Naphthol 0.47449 144.17 O.! NaNO2 0.00689 68.99 0.1 1 Acid Orange

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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Fill in the reagents table below:
Substance
Mass (g)
MW (g/mol)
Mmol
Equivalents
2-Naphthol
Write the safety precautions for each chemical
Sulfanilic Acid
Sodium Nitrite
Acid Orange
Sulfanilic acid
6.417329
173.2
0.1
1
Ethyl Acetate
2-Naphthol
NaNO2
0.47449 0.00689
68.99
144.17
0.1
0.1
I
Acid Orange
What solvent is used in this reaction, and how much of it is needed?
Draw the mechanism for the generation of the nitrosonium (NO) ion from sodium
nitrite and sulfuric acid:
Greener Organic Experiments 91
Transcribed Image Text:Fill in the reagents table below: Substance Mass (g) MW (g/mol) Mmol Equivalents 2-Naphthol Write the safety precautions for each chemical Sulfanilic Acid Sodium Nitrite Acid Orange Sulfanilic acid 6.417329 173.2 0.1 1 Ethyl Acetate 2-Naphthol NaNO2 0.47449 0.00689 68.99 144.17 0.1 0.1 I Acid Orange What solvent is used in this reaction, and how much of it is needed? Draw the mechanism for the generation of the nitrosonium (NO) ion from sodium nitrite and sulfuric acid: Greener Organic Experiments 91
Post-Lab Discussion
Weight of Product 350.33
Melting Point
164°C
Atom Economy 20.22%
E=
% Yield
60%
Literature M.P. 164 °C
NaO3S
Atom Efficiency
Amax =
How would the yield change if the dye was washed with cold water instead of cold
ethanol?
HN-N-
483nm
How is the resonance form of Acid Orange, drawn below, obtained? Redraw the
molecule and show all arrows in your rationale.
Transcribed Image Text:Post-Lab Discussion Weight of Product 350.33 Melting Point 164°C Atom Economy 20.22% E= % Yield 60% Literature M.P. 164 °C NaO3S Atom Efficiency Amax = How would the yield change if the dye was washed with cold water instead of cold ethanol? HN-N- 483nm How is the resonance form of Acid Orange, drawn below, obtained? Redraw the molecule and show all arrows in your rationale.
Expert Solution
Step 1

Sulfanilic acid(4-aminobenzenesulfonic acid) reacts with 2-napthol in presence of NaNO2 to form a azo dye called acid orange (2-naphthol orange). This is formed from the azo coupling reaction between diazotized Sulfanilic acid and β-naphthol (2-napthol).

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