Nitration of Methyl Benzoate (1)Hydrocarbons do not dissolve in concentrated sul
ID: 1034341 • Letter: N
Question
Nitration of Methyl Benzoate
(1)Hydrocarbons do not dissolve in concentrated sulfuric acid but methyl benzoate does. Explain this difference and write an equation showing the ions that are produced
(2) Why is the product of this reaction methyl 3-nitrobenzoate and not methyl 4-nitrobenzoate? Use resonance structures to illustrate your point.
(3) What would you expect the structure of the dinitro ester to be? Consider the directing effects of the ester and the first nitro group upon the addition of the second nitro group
(4) Draw resonance structures to show in which position nitrobenzene will nitrate to form dinitrobenzene .
(5) Why are concentrated nitric and sulfuric acids used in this experiment instead of dilute acids? (HINT: You may want to consider the details of the mechanism for this reaction.)
Explanation / Answer
Methyl benzoate has an oxygen molecule which forms an alkyl oxonium ion which is soluble in sulfuric acid.Hydrocarbons are chains of carbon and hydrogen whereas methyl benzoate is an ester. Sulfuric acid protonates the carbonyl group in methyl benzoate to produce ions. Methyl m-nitrobenzoate is formed.
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