NVAMediumJEE 2023Proteins (Amino Acids, Structure, Denaturation)

JEE Chemistry 2023 Question with Solution

In an oligopeptide named Alanylglycylphenylalanylisoleucine, the number of sp2sp^2 hybridised carbons is _____.

Answer

Correct answer:10

Step-by-step solution

Standard Method

Given: The oligopeptide is Alanylglycylphenylalanylisoleucine.

Find: The number of sp2sp^2 hybridised carbon atoms.

From the given structure, identify carbon atoms that are sp2sp^2 hybridised.

The following carbons are sp2sp^2 hybridised:

  1. The carbonyl carbon of the peptide bond between alanine and glycine.
  2. The carbonyl carbon of the peptide bond between phenylalanine and alanine.
  3. The carbonyl carbon of the carboxyl group at the C-terminal of isoleucine.
  4. The carbons of the phenyl group in phenylalanine.

Hence, counting all the sp2sp^2 hybridised carbons in the structure:

  • One from each of the peptide bonds.
  • One from the carboxyl group.
  • The aromatic ring carbons in phenylalanine.

Thus, the total number of sp2sp^2 hybridised carbons is 1010.

Therefore, the required answer is 1010.

Recognition Trick

Given: The peptide contains peptide carbonyl groups, one terminal carboxyl group, and one phenyl ring.

Find: The total number of sp2sp^2 hybridised carbons.

A quick way is to count standard sp2sp^2 carbon sources:

  • Each peptide bond contributes one carbonyl carbon.
  • The terminal carboxyl group contributes one carbonyl carbon.
  • The phenyl ring contributes six sp2sp^2 carbons.

Adding these contributions gives the final count as 1010.

Therefore, the correct numerical value is 1010.

Common mistakes

  • Counting only the carbonyl carbons and forgetting the aromatic ring carbons is incorrect because all six carbons of the phenyl ring are sp2sp^2 hybridised. Include both carbonyl and aromatic sp2sp^2 carbons.

  • Treating peptide-bond carbonyl carbons as sp3sp^3 is wrong because a carbonyl carbon is trigonal planar and therefore sp2sp^2 hybridised. Identify every C=OC=O carbon separately.

  • Missing the terminal carboxyl-group carbonyl carbon leads to an undercount. In addition to peptide bonds, also check the C-terminal carboxyl group.

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