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Chapter 11: Problem 62

Draw a Lewis structure for the urea molecule, \(\mathrm{CO}\left(\mathrm{NH}_{2}\right)_{2},\) and predict its geometric shape with the VSEPR theory. Then revise your assessment of this molecule, given the fact that all the atoms lie in the same plane, and all the bond angles are \(120^{\circ} .\) Propose a hybridization and bonding scheme consistent with these experimental observations.

Short Answer

Expert verified
The urea molecule \(\mathrm{CO}\left(\mathrm{NH}_{2}\right)_{2}\) has a Lewis structure where carbon is double bonded to oxygen and single-bonded to the nitrogen atoms (which are each single-bonded to two hydrogen atoms). The initial prediction of a tetrahedral molecular shape (based on VSEPR theory) is revised to a trigonal planar shape to match the given experimental data. The carbon atom achieves this shape through sp2 hybridization, suggesting a bonding scheme where each sp2 hybrid orbital forms a sigma bond with the oxygen or nitrogen atoms, and the remaining 2p orbital forms a pi bond with the oxygen atom.

Step by step solution

01

Draw the Lewis Structure

A Lewis structure shows the placement of atoms and respective lone pairs and bonding pairs of electrons. The important part is finding how many valence electrons are available and placing these electrons around the atoms. The urea molecule, \(\mathrm{CO}\left(\mathrm{NH}_{2}\right)_{2}\), is composed of one carbon atom, one oxygen atom, and two nitrogen atoms, each bonded to two hydrogen atoms. The number of valence electrons totals to 24. When you place these electrons around the atoms, keep the rule of octet in mind. This would result in the formation of double bond between carbon and oxygen atoms, and single bonds between nitrogen and hydrogen atoms, as well as carbon and nitrogen atoms.
02

Predict the Shape Using VSEPR Theory

The Valence-Shell Electron-Pair Repulsion (VSEPR) theory allows us to predict the shape of molecules based on their Lewis structure. The electron pairs around the central atom lead to a tetrahedral shape according to VSEPR theory because carbon is the central atom and has four areas of electron density (the oxygen atom and three nitrogen atoms).
03

Revise the Shape to Fit Given Data

However, this prediction doesn't match up with the given experimental observations. It's been given that all atoms lie in the same plane and the bond angles are 120 degrees. This suggests that the molecule has a trigonal planar shape.
04

Propose a Hybridization and Bonding Scheme

Hybridization refers to the combining of atomic orbitals to form the same number of equivalent hybrid orbitals. To achieve a trigonal planar structure with 120-degree bond angles, the central carbon atom would need to be sp2 hybridized. Under this scheme, there would be one 2s orbital and two 2p orbitals combining to form three sp2 hybrid orbitals, with each one forming a sigma bond with the oxygen atom or a nitrogen atom. The remaining unhybridized 2p orbital on the carbon atom will form a pi bond with the oxygen atom, completing the double bond.

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Most popular questions from this chapter

Consider the molecules \(\mathrm{NO}^{+}\) and \(\mathrm{N}_{2}^{+}\) and use molecular orbital theory to answer the following: (a) Write the molecular orbital configuration of each ion (ignore the 1 s electrons). (b) Predict the bond order of each ion. (c) Which of these ions is paramagnetic? Which is diamagnetic? (d) Which of these ions do you think has the greater bond length? Explain.

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