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Chemistry & Chemical Reactivity

10th Edition
John C. Kotz + 3 others
ISBN: 9781337399074

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BuyFindarrow_forward

Chemistry & Chemical Reactivity

10th Edition
John C. Kotz + 3 others
ISBN: 9781337399074
Textbook Problem

When two amino acids react with each other, they form a linkage called an amide group, or a peptide link. (If more linkage. are added, a protein or polypeptide is formed.)

(a) What are the hybridizations of the C and N atoms in the peptide linkage?

(b) Is the structure illustrated the only resonance structure possible for the peptide linkage? If another resonance structure is possible. compare it with the o ne shown. Decide which is the more important structure.

(c) The computer-generated structure shown here, which contains a peptide linkage, shows that this linkage is flat. This is an important feature of proteins. Speculate on reasons that the CO—NH linkage is planar. What are the sites of positive and negative charge in this dipeptide?

images

(a)

Interpretation Introduction

Interpretation:

The hybridization of the CandN atoms in the peptide linkage should be determined.

Concept Introduction

Hybridization:  When the atomic orbitals mix to form new atomic orbitals, the new orbitals have the same total electron capacity as the old ones. The properties and energies of the new, hybridized orbitals are an 'average' of the original unhybridized orbitals.

sp2 hybridization: This concept  has intermixing of one s-orbitals and two p-orbitals to give three identical hybrid orbitals is known as Sp2 or trigonal hybridization".

sp3 hybridization: This concept  has intermixing of one s-orbitals and three p-orbitals to give four identical hybrid orbitals is known as Sp3 or tetragonal hybridization".

Explanation

 Hybridization of carbon and nitrogen atom in peptide linkage can be determined as follows,

The formation peptide bond is given below,

(b)

Interpretation Introduction

Interpretation:

Check whether the given structure of peptide illustrates only the possible resonance structure for it or not.

Concept Introduction

Resonance: This method within the VBT theory of bonding that describes the delocalization of electrons within molecules. It compares and contrasts two or more possible Lewis structure that can represent particular functional groups.

(c)

Interpretation Introduction

Interpretation:

Speculate on reasons that the CONH linkage is planar. The sites of positive and negative charge in the given dipeptide should be identified.

Concept Introduction

When all the atoms in a molecule lie in the same plane then it is said to be planar molecule.

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