Compound A of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{~N}_{2} \mathrm{O}_{2}\) reacts with aqueous nitrous acid to give compound \(B\) of formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{4}\). Compound B readily loses water on heating to give \(\mathrm{C}, \mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{3}\). Compound A can also react with a solution of bromine and sodium hydroxide in water to give \(\mathrm{D}, \mathrm{C}_{4} \mathrm{H}_{12} \mathrm{~N}_{2}\), which on treatment with nitrous acid and perchloric acid gives methyl ethyl ketone. Write structures of all compounds and the equations involved.

Short Answer

Expert verified
Compound A is a dipeptide Gly-Ala with the molecular formula \(\mathrm{C}_6\mathrm{H}_{12}\mathrm{N}_2\mathrm{O}_2\), and its structure is: \(\mathrm{H}_{2}\mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NH}-\mathrm{CH}_{3}-\mathrm{COOH}\). A reacts with aqueous nitrous acid to form B, losing two hydrogen atoms and gaining two oxygen atoms: \(\mathrm{H}_{2}\mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NO}-\mathrm{CH}_{3}-\mathrm{COOH}\). B loses water upon heating to form C: \(\mathrm{H}_{2}\mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NO}-\mathrm{CH}_{3}-\mathrm{CO}\). A reacts with bromine and sodium hydroxide to form D: \(\mathrm{H}_{2}\mathrm{N}-\mathrm{CH}_{2}\mathrm{NH}_{2}\) and \(\mathrm{H}_{2}\mathrm{N}-\mathrm{CH}_{3}\). D reacts with nitrous and perchloric acids to produce methyl ethyl ketone: \(\mathrm{CH}_{3}\mathrm{COCH}_{2}\mathrm{CH}_{3}\).

Step by step solution

01

Analyzing the Reactions

First, we need to analyze the given information and understand what happens during each chemical reaction. 1. Compound A \((\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{N}_{2} \mathrm{O}_{2})\) reacts with aqueous nitrous acid to form compound B \((\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{4})\). 2. Compound B loses water on heating to form compound C \((\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{3})\). 3. Compound A also reacts with a solution of bromine and sodium hydroxide in water to form compound D \((\mathrm{C}_{4} \mathrm{H}_{12} \mathrm{N}_{2})\), which upon treatment with nitrous acid and perchloric acid gives methyl ethyl ketone. Let's move on to identifying the structures of each compound, starting with compound A.
02

Identifying the Structure of Compound A

The molecular formula of compound A is \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{N}_{2} \mathrm{O}_{2}\). The nitrogen and oxygen atoms in the molecular formula suggest that it could be a dipeptide. This is supported by the fact that compound A reacts with bromine and sodium hydroxide, which is the reaction to determine amino acid content in protein analysis. The reaction between nitrous and perchloric acids suggests that the amino groups produce methyl ethyl ketone, so we can identify the amino acids as glycine (Gly) and alanine (Ala). Thus, the structure of compound A can be represented as Gly-Ala: \[ \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NH}-\mathrm{CH}_{3}-\mathrm{COOH} \]
03

Writing the Reaction Equation for Compound B

Compound A reacts with aqueous nitrous acid, which causes the loss of two hydrogen atoms and gaining two oxygen atoms, creating compound B with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{4}\). The reaction can be written as: \[ \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NH}-\mathrm{CH}_{3}-\mathrm{COOH} + 2\mathrm{HNO}_2 \rightarrow \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NO}-\mathrm{CH}_{3}-\mathrm{COOH} + 2\mathrm{H}_2\mathrm{O} \]
04

Writing the Reaction Equation for Compound C

Compound B loses water upon heating, which causes the molecular formula to change to \(\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{3}\), forming compound C. The reaction can be written as: \[ \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NO}-\mathrm{CH}_{3}-\mathrm{COOH} \xrightarrow{\triangle} \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NO}-\mathrm{CH}_{3}-\mathrm{CO} + \mathrm{H}_{2}\mathrm{O} \]
05

Writing the Reaction Equation for Compound D

Compound A reacts with a solution of bromine and sodium hydroxide in water to form compound D \((\mathrm{C}_{4} \mathrm{H}_{12} \mathrm{N}_{2})\). The reaction can be written as: \[ \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{CO}-\mathrm{NH}-\mathrm{CH}_{3}-\mathrm{COOH} + 2\mathrm{NaBr} + 2\mathrm{NaOH} \rightarrow \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{NH}_{2} + \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{3} + 2\mathrm{Na}_{2}\mathrm{CO}_{3} + 2\mathrm{H}_{2}\mathrm{O} \]
06

Writing the Reaction Equation for Methyl Ethyl Ketone formation

Compound D, upon treatment with nitrous acid and perchloric acid, results in the formation of methyl ethyl ketone. The reaction can be written as: \[ \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{2}\mathrm{NH}_{2} + \mathrm{H}_{2} \mathrm{N}-\mathrm{CH}_{3} + 2\mathrm{HNO}_2 + 2\mathrm{HClO}_4 \rightarrow \mathrm{CH}_{3}\mathrm{COCH}_{2}\mathrm{CH}_{3} + 2\mathrm{N}_{2} + 4\mathrm{H}_{2}\mathrm{O} \]

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