Considering the reaction sequence given below, the correct statement(s) is(are)
Correct Answer :
Treating P with conc. NH4OH solution followed by acidification gives Q.
Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
P is more acidic than CH3CH2COOH.
Solution :
The correct statements are:
1. Treating P with conc. NH4OH solution followed by acidification gives Q.
2. Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
3. P is more acidic than CH3CH2COOH.
Step-by-Step Analysis of the Reaction Sequence:
The given image shows the following reaction scheme:
1. Formation of Compound P:
Propanoic acid () reacts with in the presence of red phosphorus followed by hydrolysis (). This is the Hell-Volhard-Zelinsky (HVZ) reaction, which causes α-bromination of carboxylic acids.
Thus, compound P is 2-bromopropanoic acid:
2. Formation of Compound Q:
Compound P undergoes reaction with potassium phthalimide, followed by alkaline hydrolysis () and acidification (). This is the Gabriel Phthalimide Synthesis, which converts an alkyl halide into a primary amine without affecting the carboxylic group. Phthalic acid is formed as a side product.
Thus, compound Q is alanine (2-aminopropanoic acid):
Evaluation of the Given Statements:
Statement 1: "P can be reduced to a primary alcohol using NaBH4."
is a weak reducing agent that reduces aldehydes and ketones but generally does not reduce carboxylic acid groups () to alcohols. Therefore, P cannot be reduced to a primary alcohol using . Thus, this statement is incorrect.
Statement 2: "Treating P with conc. NH4OH solution followed by acidification gives Q."
When 2-bromopropanoic acid (P) is treated with concentrated ammonia/ammonium hydroxide (), nucleophilic substitution () occurs where the bromide () group is substituted by an amino () group, yielding 2-aminopropanoic acid (alanine, Q). Thus, this statement is correct.
Statement 3: "Treating Q with a solution of NaNO2 in aq. HCl liberates N2."
Compound Q is an aliphatic primary amine (an α-amino acid). Aliphatic primary amines react with nitrous acid () to form highly unstable aliphatic diazonium salts, which decompose immediately to release nitrogen gas () quantitatively along with alcohols/hydroxy acids. Thus, this statement is correct.
Statement 4: "P is more acidic than CH3CH2COOH."
Compound P (2-bromopropanoic acid) contains an electronegative bromine atom at the α-position. Bromine exerts an electron-withdrawing inductive effect ( effect), which stabilizes the carboxylate anion formed after deprotonation. Consequently, P is significantly more acidic than unsubstituted propanoic acid (). Thus, this statement is correct.
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