Which is the limiting factor if we have: 0.015 moles of sulfunilic acid 0.010 moles of sodium carbonate 0.012 moles of sodium nitrite excess HCl, explain your reasoning and calculate theoratical yield.

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Which is the limiting factor if we have:

0.015 moles of sulfunilic acid

0.010 moles of sodium carbonate

0.012 moles of sodium nitrite

excess HCl,

explain your reasoning and calculate theoratical yield.

You will synthesize methyl orange from sulfanilic acid and N,N-dimethylaniline using a
coupling reaction just like the one you saw in the previous experiment in the nitrous acid test for
aromatic amines. The overall reaction is shown in Figure 17.2 and the mechanism is shown inf
of this chemistry is in your text in the chapter on amines. You need to understand it.
Figure 17.2 Preparation of Methyl Orange
CH,
CF
1. Na,CO3
NH2
HO-
HO S
NEN
CH3
2. NaNO2
3. HСІ
sulfanilic acid
CH3
HO
CH3
methyl or ange
The first step is simply an acid base reaction. In order to dissolve the sulfanilic acid in t
solution we add sodium carbonate. Then we form the diazonium salt by the same mechanism t
presented in Figure 16.4 of the previous experiment. When we add the HCI, the nitroso ion is f
sodium nitrite and this reacts with the amine to form a nitrosoammonium adduct that loses wate
acidic conditions after proton transfer. This gives the diazonium salt. Aromatic diazonium salt
low temperature. The terminal nitrogen of the diazonium salt is very electron deficient. It can
good nucleophiles. We dissolve the dimethylaniline in acetic acid. This forms the dimethylani
which is soluble in water but not nucleophilic. Slow addition of sodium hydroxide neutralizes
amine of the N,N-dimethylaniline acetate salt in situ and the dimethylaniline becomes a good n
the activating effect of the dimethylamine substituent. Attack is in the para position due to hine
ortho norition hy the bulky dimethylamine substituent.
Transcribed Image Text:You will synthesize methyl orange from sulfanilic acid and N,N-dimethylaniline using a coupling reaction just like the one you saw in the previous experiment in the nitrous acid test for aromatic amines. The overall reaction is shown in Figure 17.2 and the mechanism is shown inf of this chemistry is in your text in the chapter on amines. You need to understand it. Figure 17.2 Preparation of Methyl Orange CH, CF 1. Na,CO3 NH2 HO- HO S NEN CH3 2. NaNO2 3. HСІ sulfanilic acid CH3 HO CH3 methyl or ange The first step is simply an acid base reaction. In order to dissolve the sulfanilic acid in t solution we add sodium carbonate. Then we form the diazonium salt by the same mechanism t presented in Figure 16.4 of the previous experiment. When we add the HCI, the nitroso ion is f sodium nitrite and this reacts with the amine to form a nitrosoammonium adduct that loses wate acidic conditions after proton transfer. This gives the diazonium salt. Aromatic diazonium salt low temperature. The terminal nitrogen of the diazonium salt is very electron deficient. It can good nucleophiles. We dissolve the dimethylaniline in acetic acid. This forms the dimethylani which is soluble in water but not nucleophilic. Slow addition of sodium hydroxide neutralizes amine of the N,N-dimethylaniline acetate salt in situ and the dimethylaniline becomes a good n the activating effect of the dimethylamine substituent. Attack is in the para position due to hine ortho norition hy the bulky dimethylamine substituent.
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