Reaction of glycine with \(\mathrm{NaNO}_{2}\) and \(\mathrm{HCl}\) gives (a) acetic acid (b) glycolic acid (c) oxalic acid (d) nitroacetic acid

Short Answer

Expert verified
Answer: (d) nitroacetic acid

Step by step solution

01

Write down the reaction and the structure of glycine

First, we need to write down the reaction of glycine with NaNO2 and HCl, as well as the structure of glycine. Glycine has the molecular formula NH2CH2COOH, which means it has an amino group (NH2) and a carboxyl group (COOH) attached to the same carbon atom. The reaction is as follows: NH2CH2COOH + NaNO2 + HCl → ?
02

Examine the reaction of the amino group with NaNO2 and HCl

Sodium nitrite (NaNO2) and hydrochloric acid (HCl) react together to form nitrous acid (HNO2) and sodium chloride (NaCl): NaNO2 + HCl → HNO2 + NaCl Now, the amino group of glycine can react with nitrous acid (HNO2) to form a diazonium ion. The reaction can be written as: NH2CH2COOH + HNO2 → N2+CH2COOH + H2O
03

Identify the possible products

Now, we need to identify the possible products from the given options based on the diazonium ion formed in the reaction. The diazonium ion can either lose a nitrogen molecule to form a carbocation or it can replace the nitrogen with a nitro group to form nitroacetic acid. Option (a) acetic acid: There is no possible way for the diazonium ion to lose both the amino and carboxyl groups and form acetic acid. Option (b) glycolic acid: The diazonium ion can lose a nitrogen molecule to form a carbocation; however, this would result in the formation of an unstable intermediate which is very unlikely. Option (c) oxalic acid: The diazonium ion does not have any possibility of being converted into oxalic acid, as it requires a different type of reaction and set of reactants. Option (d) nitroacetic acid: It is possible that the diazonium ion undergoes a substitution reaction to replace the nitrogen with a nitro group. This would result in the formation of nitroacetic acid.
04

Determine the product

From the analysis in Step 3, the most likely product is nitroacetic acid (option d). This is because it involves a reaction of the diazonium ion with the reactants (NaNO2 and HCl) to form nitroacetic acid. Thus, the correct answer is (d) nitroacetic acid.

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