JEE Main · 2019 · Shift-ImediumBIO-119

The correct structure of product 'P' in the following reaction is: Asn - Ser + (CH3CO)2O - [NEt3] P

Biomolecules · Class 12 · JEE Main Previous Year Question

Question

The correct structure of product 'P' in the following reaction is: \ceAsnSer+(CH3CO)2O>[NEt3]P\ce{Asn - Ser + (CH3CO)_2O -> [NEt3] P} image

Options
  1. a

    Option a

  2. b

    Option b

  3. c

    Option c

  4. d

    Option d

Correct Answerb

Option b

Detailed Solution

Step 1: Substrate Analysis — The peptide Asn-Ser (Asparagine-Serine) possesses a primary amino group (at the N-terminal end) and a primary alcohol group (on the serine side chain).

Step 2: Acetylation Reaction — Under basic conditions with acetic anhydride ((\ceCH3CO)2\ceO(\ce{CH3CO})_2\ce{O}), both the amino (\ceNH2-\ce{NH2}) and alcohol (\ceOH-\ce{OH}) groups will be acetylated.

Step 3: Resulting Structure — Structure (b) accurately reflects the derivative where both these groups have undergone substitution. Correct option is (b).

Key Point: Tertiary amines like triethylamine (NEt3NEt_3) act as catalysts/bases in these nucleophilic substitution reactions.

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The correct structure of product 'P' in the following reaction is: Asn - Ser + (CH3CO)2O - [NEt3] P (JEE Main 2019) | Canvas Classes