JEE Challenger
More from Biomolecules

Synthesis and Identification of Amino Acid T

Comprehension Passage

Upon reaction of compound O with KMnO4/H+\text{KMnO}_4/\text{H}^+, compound P is formed, which when heated with ammonia yields Q. Treatment of compound Q with Br2/NaOH\text{Br}_2/\text{NaOH} produces R. When strongly heated, Q yields S, which upon subsequent reaction with ethyl 2-bromopropanoate in the presence of KOH\text{KOH} followed by acidification, gives compound T.

Passage Diagram 1

Identify compound T.

Options

A

glycine

B

alanine

Correct
C

valine

D

serine

Step-by-Step Solution

To determine the identity of compound T, we trace the reaction sequence step by step starting from compound O:

  1. Oxidation of Compound O to Compound P: Compound O is 1,21,2-dipropylbenzene (an ortho-dialkylbenzene). Vigorous oxidation of 1,21,2-dipropylbenzene using acidic potassium permanganate (KMnO4/H+\text{KMnO}_4/\text{H}^+) cleaves the alkyl side-chains at the benzylic position to yield phthalic acid (benzene-1,21,2-dicarboxylic acid) as compound P: O (1,2-dipropylbenzene)→KMnO4/H+P (Phthalic acid)\text{\textbf{O}} \,(1,2\text{-dipropylbenzene}) \xrightarrow{\text{KMnO}_4/\text{H}^+} \text{\textbf{P}} \,(\text{Phthalic acid})

  2. Formation of Compound Q: Reaction of phthalic acid (P) with ammonia (NH3\text{NH}_3) followed by heating gives phthalamide (Q): P (Phthalic acid)→ΔNH3Q (Phthalamide)\text{\textbf{P}} \,(\text{Phthalic acid}) \xrightarrow[\Delta]{\text{NH}_3} \text{\textbf{Q}} \,(\text{Phthalamide})

  3. Formation of Compound S: Strong heating of phthalamide (Q) results in the elimination of a molecule of ammonia (NH3\text{NH}_3), leading to cyclization and formation of phthalimide (S): Q (Phthalamide)→Strong HeatingS (Phthalimide)+NH3↑\text{\textbf{Q}} \,(\text{Phthalamide}) \xrightarrow{\text{Strong Heating}} \text{\textbf{S}} \,(\text{Phthalimide}) + \text{NH}_3\uparrow

  4. Gabriel Phthalimide Synthesis to form Compound T: Phthalimide (S) undergoes a Gabriel synthesis reaction:

    • Treatment with KOH\text{KOH} deprotonates the imide nitrogen to form potassium phthalimide: Phthalimide+KOH→Potassium phthalimide+H2O\text{Phthalimide} + \text{KOH} \rightarrow \text{Potassium phthalimide} + \text{H}_2\text{O}
    • Potassium phthalimide undergoes an SN2\text{S}_\text{N}2 nucleophilic substitution reaction with ethyl 22-bromopropanoate (CH3CH(Br)COOCH2CH3\text{CH}_3\text{CH(Br)COOCH}_2\text{CH}_3) to yield NN-(1-ethoxycarbonylethyl)phthalimide.
    • Subsequent acidic hydrolysis (acidification) cleaves the amide linkage and hydrolyzes the ethyl ester group, releasing phthalic acid and the α\alpha-amino acid alanine (CH3-CH(NH2)-COOH\text{CH}_3\text{-CH(NH}_2\text{)-COOH}): S→(1) KOH,  (2) CH3CH(Br)COOCH2CH3,  (3) H3O+T (Alanine)\text{\textbf{S}} \xrightarrow{(1)\,\text{KOH}, \; (2)\,\text{CH}_3\text{CH(Br)COOCH}_2\text{CH}_3, \; (3)\,\text{H}_3\text{O}^+} \text{\textbf{T}} \,(\text{Alanine})

Thus, compound T is alanine.

Correct Option: B