Question Details

Considering the reaction sequence given below, the correct statement(s) is(are)


Options

A

P can be reduced to a primary alcohol using NaBH4.

B

Treating P with conc. NH4OH solution followed by acidification gives Q.

C

Treating Q with a solution of NaNO2 in aq. HCl liberates N2.

D

P is more acidic than CH3CH2COOH.

Show Answer

Correct Answer :

Option B

Treating P with conc. NH4OH solution followed by acidification gives Q.

Option C

Treating Q with a solution of NaNO2 in aq. HCl liberates N2.

Option D

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 (CH3CH2COOH) reacts with Br2 in the presence of red phosphorus followed by hydrolysis (H2O). This is the Hell-Volhard-Zelinsky (HVZ) reaction, which causes α-bromination of carboxylic acids.

Thus, compound P is 2-bromopropanoic acid:

P=CH3CH(Br)COOH

2. Formation of Compound Q:
Compound P undergoes reaction with potassium phthalimide, followed by alkaline hydrolysis (NaOH) and acidification (H3O+). 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):

Q=CH3CH(NH2)COOH

Evaluation of the Given Statements:

Statement 1: "P can be reduced to a primary alcohol using NaBH4."
NaBH4 is a weak reducing agent that reduces aldehydes and ketones but generally does not reduce carboxylic acid groups (-COOH) to alcohols. Therefore, P cannot be reduced to a primary alcohol using NaBH4. 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 (NH4OH), nucleophilic substitution (SN2) occurs where the bromide (-Br) group is substituted by an amino (-NH2) 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 (NaNO2+HCl) to form highly unstable aliphatic diazonium salts, which decompose immediately to release nitrogen gas (N2) 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 (-I effect), which stabilizes the carboxylate anion formed after deprotonation. Consequently, P is significantly more acidic than unsubstituted propanoic acid (CH3CH2COOH). Thus, this statement is correct.

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