Given The Electron Configuration For C and H, Imagine How Their Atomic Orbitals Might Overlap

1.
9 Hybridized Atomic Orbitals

• Given the electron configuration for C and H, imagine how their atomic orbitals
might overlap
• Would such orbital overlap

yield methane?
Copyright 2012 John Wiley & Sons, Inc.

1 Klein, Organic Chemistry 2e
1.9 Hybridized Atomic Orbitals
• To make methane, the C atom must have 4 atomic orbitals available for overlapping
• If an electron is excited from the 2s to the 2p, will that make it suitable for making methane?
• If four H atoms were to come in and overlap with the 2s and 2p orbitals, what geometry
would the resulting methane have?

• The carbon must undergo hybridization to form 4 equal
atomic orbitals
• The atomic orbitals must be equal in energy to form four
equal-energy symmetrical C-H bonds

• Should the shape of an sp3 orbital look more like an s or more

like p orbital?

• To make CH4, the 1s atomic orbitals of the H atoms will
overlap with the four sp3 hybrid atomic orbitals of C

• Draw a picture that shows the necessary atomic orbitals and their overlap to form ethane (C 2H6).
• Draw a picture that shows the necessary atomic orbitals and their overlap to form water.
• Practice with conceptual checkpoint 1.19

• Consider ethene (ethylene).
• Each carbon in ethene must bond to three other atoms,

so only three hybridized atomic orbitals are needed

• An sp2 hybridized carbon will have three equal-energy
sp2 orbitals and one unhybridized p orbital

• The sp2 atomic orbitals overlap to form sigma (σ) bonds
• Sigma bonds provide maximum HEAD-ON overlap

• The unhybridized p orbitals in ethene form pi (π) bonds, SIDE-BY-SIDE overlap
• Practice with conceptual checkpoint 1.20

• The unhybridized p orbitals in ethene form pi (π) bonds,
SIDE-BY-SIDE overlap of p-orbitals giving both
CONSTRUCTIVE and DESTRUCTIVE interference
• MO theory provides
a similar picture.
Remember, red and
blue regions are all
part of the same
orbital

• Why is sp2 hybridization not appropriate for methane

(CH4)?

• Consider ethyne (acetylene).
• Each carbon in ethyne must bond to two other atoms, so

only two hybridized atomic orbitals are needed

• The sp atomic orbitals overlap HEAD-ON to form sigma
(σ) bonds while the unhybridized p orbitals overlap SIDE-
BY-SIDE to form pi bonds
• Practice with
SkillBuilder 1.7

• Which should be stronger, a pi bond or a sigma bond? WHY?
• Which should be longer, an sp3 – sp3 sigma bond overlap or an

sp – sp sigma bond overlap?

• Explain the different strengths and lengths below.
• Practice with
conceptual
checkpoint
1.24

1.10 Molecular Geometry
• Valence shell electron pair repulsion (VSEPR theory)
– Valence electrons (bonded and lone pairs) repel each other
• To determine molecular geometry…
1. Determine the Steric number

1.10 Molecular Geometry
• Valence shell electron pair repulsion (VSEPR theory)
– Valence electrons (bonded and lone pairs) repel each other
• To determine molecular geometry…
2. Predict the hybridization of the central atom
• If the Steric number is 4, then it is sp3
• If the Steric number is 3, then it is sp2
• If the Steric number is 2, then it is sp

1.10 sp3 Geometry
• For any sp3 hybridized atom, the 4 valence electron pairs
will form a tetrahedral electron group geometry
• Methane has 4 equal • How does the lone • The bond angels in
bonds, so the bond pair of ammonia oxygen are even
angles are equal affect its geometry? smaller, why?

1.10 sp3 Geometry
• The molecular geometry is different from the electron
group geometry. HOW?

1.10 sp2 Geometry
• Calculate the Steric number for BF3
• Electron pairs that are located in sp2 hybridized orbitals will form a trigonal planar electron group geometry
• What will be the molecular geometry?

1.10 sp2 Geometry
• How many electrons are in Boron’s unhybridized p orbital?
• Does this geometry follow VSEPR theory?

1.10 sp2 Geometry
Analyze the steric number, hybridization, electron group
geometry and molecular geometry for this imine?

1.10 sp Geometry
• Analyze the Steric number, the hybridization, the electron group geometry, and the molecular geometry for the following molecules
• BeH2
• CO2

1.10 Geometry Summary
• Practice with
SkillBuilder 1.8

1.11 Molecular Polarity
• Electronegativity Differences cause induction
• Induction (shifting of electrons WITHIN their orbitals)
results in a dipole moment.
• Dipole moment = (the amount of partial charge) x (the
distance the δ+ and δ- are separated)
• Dipole moments are reported in units of debye (D)
• 1 debye = 10-18 esu ∙ cm
– An esu is a unit of charge. 1 e- has a charge of 4.80 x 10-10 esu
– cm are included in the unit, because the distance between the
centers of + and – charges affects the dipole

• Consider the dipole for CH3Cl
• Dipole moment (μ) = charge (e) x distance (d)
– Plug in the charge and distance
• μ = (1.056 x 10-10 esu) x (1.772 x 10-8 cm)
– Note that the amount of charge separation is
less than what it would be if it were a full
charge separation (4.80 x 10-10 esu)
• μ = 1.87 x 10-18 esu ∙ cm
– Convert to debye
• μ = 1.87 D

• What would the dipole moment be if CH3Cl were 100%
ionic?
• μ = charge (e) x distance (d)
– Plug in the charge and distance
• μ = (4.80 x 10-10 esu) x (1.772 x 10-8 cm)
– The full charge of an electron is plugged in
• μ = 8.51 x 10-18 esu ∙ cm = 8.51 D
• What % of the C-Cl bond is ionic?
• Is the C-Cl bond mostly ionic or mostly
covalent?

1-28
• Check out the polarity of come other common bonds

• Why is the C=O double bond so much more polar than
the C-O single bond?

• For molecules with multiple polar bonds, the dipole
moment is the vector sum of all of the individual bond
dipoles

• It is important to determine a molecule’s geometry FIRST before analyzing its polarity
• If you have not drawn the molecule with the proper geometry, it may cause you to
assess the polarity wrong as well
• Would the dipole for water be different if it were linear rather than angular?

• Electrostatic potential maps are often used to give a
visual depiction of polarity

• Practice with SkillBuilder 1.9

• Explain why the dipole moment for pentane = 0 D

Study Guide for sections 1.9-1.11
DAY 2, Terms to know:
Sections 1.9-1.11 hybridized atomic orbitals, steric number, degenerate orbitals, pi bond,
sigma bond, electron group geometry, molecular geometry, induction, dipole moment
DAY 2, Specific outcomes and skills that may be tested on exam 1:
Sections 1.9-1.11
•Be able to predict what type of hybridization atomic orbitals will undergo for an atom
depending on the bonding and steric number of the atom.
•Be able to explain how the ratio of s and p orbitals mixed into the hybrid atomic orbitals
affects the shape and energy of the resulting hydridized orbitals.
•Be able to draw a picture showing the overlapping of the correct atomic orbitals for small
molecules with 8 atoms or less including molecules with single, double, and triple bonds.
•Be able to predict where molecules will have pi bonds and sigma bonds between atoms.
•Be able to predict the steric number, hybridization, electron group geometry, molecular
geometry, and approximate bond angle for atoms within molecules.
•Be able to determine the direction of dipole moment for a molecule and rate its approximate
magnitude.
•Be able to describe how molecular geometry affects polarity or dipole.

Practice Problems for sections 1.9-1.11
Complete these problems outside of class until you are confident you have learned
the SKILLS in this section outlined on the study guide and we will review some of
them next class period. 1.20 1.21 1.22 1.23 1.25 1.26 1.27 1.29 1.30 1.31
1.49 1.50 1.51 1.55 1.59

Prep for day 3
Must Watch videos:

https://www.youtube.com/watch?v=cnSTsLvyuOk (dissolving, Tyler DeWitt)
https://www.youtube.com/watch?v=_mWHWJiMKXU (solubility)
https://www.youtube.com/watch?v=RP6AS7XVIC8 (drawing organic molecules)
Other helpful videos:

http://www.youtube.com/watch?v=gxmpr09Xk4Y (solvation, Brightstorm)
https://www.youtube.com/watch?v=pMoA65Dj-zk (drawing organic molecules)
Read sections 1.12-1.13, 2.1-2.2

Given The Electron Configuration For C and H, Imagine How Their Atomic Orbitals Might Overlap

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1.

9 Hybridized Atomic Orbitals

• Would such orbital overlap

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

• Should the shape of an sp3 orbital look more like an s or more

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

• Practice with conceptual checkpoint 1.19

Copyright 2012 John Wiley & Sons, Inc.

• Each carbon in ethene must bond to three other atoms,

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

• Sigma bonds provide maximum HEAD-ON overlap

Copyright 2012 John Wiley & Sons, Inc.

• Practice with conceptual checkpoint 1.20

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

• Why is sp2 hybridization not appropriate for methane

Copyright 2012 John Wiley & Sons, Inc.

• Each carbon in ethyne must bond to two other atoms, so

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

• Which should be longer, an sp3 – sp3 sigma bond overlap or an

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

Copyright 2012 John Wiley & Sons, Inc.

• Practice with SkillBuilder 1.9

Copyright 2012 John Wiley & Sons, Inc.

• Explain why the dipole moment for pentane = 0 D

Copyright 2012 John Wiley & Sons, Inc.

36 Klein, Organic Chemistry 2e

37 Klein, Organic Chemistry 2e

Must Watch videos:

Other helpful videos:

Read sections 1.12-1.13, 2.1-2.2

38 Klein, Organic Chemistry 2e

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