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1 Organic Chemistry
The study of carbon-containing molecules and their reactions What happens to a molecule during a reaction?
A collision Bonds break/form
WHAT IS A BOND?

The BIG question: WHY do reactions occur?


We will need at least 2 semesters of your time to answer this question FOCUS ON THE ELECTRONS
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Klein, Organic Chemistry 1e

1.1 Organic Chemistry


Why do we distinguish between organic and inorganic compounds?

Why are organic compounds important?

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Klein, Organic Chemistry 1e

1.2 Structural Theory


In the mid 1800s, it was first suggested that substances are defined by a specific arrangement of atoms.
Why is a compounds formula NOT adequate to define it?

What term do we use to describe different substances with the same formula?

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Klein, Organic Chemistry 1e

1.2 Structural Theory


Atoms that are most commonly bonded to carbon include N, O, H, and halides (F, Cl, Br, I). With some exceptions, each element generally forms a specific number of bonds with other atoms

Practice with skill builder 1.1


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Klein, Organic Chemistry 1e

1.3 Covalent Bonding


A covalent bond is a PAIR of electrons shared between two atoms. For example

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Klein, Organic Chemistry 1e

1.3 Covalent Bonding


How do potential energy and stability relate?

What forces keep the bond at the optimal length?


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Klein, Organic Chemistry 1e

1.3 Atomic Structure


A review from General Chemistry
Protons (+1) and neutrons (neutral) reside in the nucleus Electrons (-1) reside outside the nucleus. WHERE? Some electrons are close to the nucleus and others are far away, WHY? Look at carbon for example. Which electrons are the valence electrons?

Why are valence electrons important?


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Klein, Organic Chemistry 1e

1.3 Counting Valence Electrons


You can always calculate the number of valence electron by analyzing the e- configuration. Look at phosphorus. Or, for Group A elements only, just look at the Group number (Roman Numeral) on the periodic table

Practice with skill builder 1.2


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Klein, Organic Chemistry 1e

1.3 Simple Lewis Structures


For simple Lewis Structures
1. Draw the individual atoms using dots to represent the valence electrons. 2. Put the atoms together so they share PAIRS of electrons to make complete octets. WHAT is an octet?

Take NH3, for example

Practice with skill builder 1.3


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Klein, Organic Chemistry 1e

1.3 Simple Lewis Structures


For simple Lewis Structures
1. Draw the individual atoms using dots to represent the valence electrons. 2. Put the atoms together so they share PAIRS of electrons to make complete octets. WHAT is an octet?

Try drawing the structure for C2H2

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Klein, Organic Chemistry 1e

1.4 Formal Charge


What term do we use to describe atoms with an unbalanced or FORMAL charge? How does formal charge affect the stability of an atom? Atoms in molecules (sharing electrons) can also have unbalanced charge, which must be analyzed, because it affects stability To calculate FORMAL charge for an atom, compare the number of valence electrons that should be associated with the atom to the number of valence electrons that are actually associated with an atom
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Klein, Organic Chemistry 1e

Lets look at a specific formal charge example. Given the Lewis structure, calculate the formal charge on each atom. or

1.4 Formal Charge

Carbon should have 4 valence e-s, because it is in group IVA on the periodic table. Carbon actually has 8 valence e-s. It needs 8 for its octet, but only 4 count towards its charge. WHY? The 4 it actually has balance out the 4 it should have, so it does not have formal charge. Its neutral.
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Klein, Organic Chemistry 1e

Lets look at the formal charge of the oxygen atom. or Oxygen should have 6 valence e-s, because it is in group VIA on the periodic table. It actually has 8 valence e-s. It needs 8 for its octet, but only 7 count towards its charge. WHY? If it actually has 7, but it should only have 6, what is its formal charge? Practice with skill builder 1.4
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1.4 Formal Charge

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Klein, Organic Chemistry 1e

Covalent bonds are electrons pairs that exist in an orbital shared between two atoms. What do you think that orbital looks like? Just like an atomic orbital, the electrons could be anywhere within that orbital region. What factors determine which atom in the bond will attract the shared electrons more?

1.5 Polar Covalent Bonds

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Klein, Organic Chemistry 1e

Covalent bonds are either polar or nonpolar

1.5 Polar Covalent Bonds

Nonpolar Covalent bonded atoms share electrons evenly Polar Covalent One of the atoms attracts electrons more than the other

Electronegativty - how strongly an atom attracts shared electrons

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Klein, Organic Chemistry 1e

Electrons tend to shift away from lower electronegativity atoms to higher electronegativity atoms.

1.5 Polar Covalent Bonds

The greater the difference in electronegativity, the more polar the bond.

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Klein, Organic Chemistry 1e

1.5 Polar Covalent Bonds


Can a bond have both covalent and ionic character?

Practice with skill builder 1.5

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


General Chemistry review In the 1920s, Quantum Mechanics was established as a theory to explain the wave properties of electrons The solution to wave equations for electrons provides us with visual pictures called orbitals

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


General Chemistry review The type or orbital be identified by its shape An orbital is a region where there is a calculated 90% probability of finding an electron. The remaining 10% probability tapers off as you move away from the nucleus

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


Electrons behave as both particles and waves. How can they be BOTH? Maybe the theory is not yet complete The theory does match experimental data, and it has predictive capability.
Like a wave on a lake, an electrons wavefunction can be (+), (-), or ZERO.

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


Because they are generated mathematically from wavefunctions, orbital regions can also be (-), (+), or ZERO
The sign of the wave function has nothing to do with electrical charge.

In this p-orbital, there is a nodal plane. The sign of the wavefunction will be important when we look at orbital overlapping in bonds.

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


Electrons are most stable (lowest in energy) if they are in the 1s orbital? The 1s orbital is full once there are two electrons in it. Why cant it fit more? The 2s orbital is filled next. The 2s orbital has a node. WHERE?

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


Once the 2s is full, electrons fill into the three degenerate 2p orbitals Where are the nodes in each of the 2p orbitals?

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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


Common elements and their electron configurations

Practice with skill builder 1.6


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Klein, Organic Chemistry 1e

1.6 Atomic Orbitals


What are the rules that govern our placement of electrons ?

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Klein, Organic Chemistry 1e

1.7 Valence Bond Theory


A bond occurs when atomic orbitals overlap. Overlapping orbitals is like overlapping waves

Only constructive interference results in a bond


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Klein, Organic Chemistry 1e

1.7 Valence Bond Theory


The bond for a H2 molecule results from constructive interference

Where do the bonded electrons spend most of their time?


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Klein, Organic Chemistry 1e

1.8 Molecular Orbital Theory


Atomic orbital wavefunctions overlap to form MOs that extend over the entire molecule. MOs are a more complete analysis of bonds, because they include both constructive and destructive interference. The number of MOs created must be equal to the number of AOs that were used.
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H2 MOs

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Klein, Organic Chemistry 1e

1.8 Molecular Orbital Theory


Why is the antibonding orbital higher in energy?

When the AOs overlap, why do the electrons go into the bonding MO rather than the antibonding MO?
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Klein, Organic Chemistry 1e

1.8 Molecular Orbital Theory


Imagine a He2 molecule. How would its MOs compare to those for H2?
How would the energy of the He2 compare to 2 He? Why does Helium exist in its atomic form rather than in molecular form? In general, if a molecule has all of it MOs occupied, will be stable or unstable?
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Klein, Organic Chemistry 1e

1.8 Molecular Orbital Theory


Consider the MOs for CHBr3
There are many areas of atomic orbital overlap Notice how the MOs extend over the entire molecule

Each picture below represents ONE orbital.

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Klein, Organic Chemistry 1e

1.8 Molecular Orbital Theory


How many electrons can fit into the areas represented in (b)?

Depending on the circumstances, we will use both MO and valence bond theory to explain phenomena.
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Klein, Organic Chemistry 1e

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?

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Klein, Organic Chemistry 1e

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?
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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


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

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals

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

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


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

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


Draw a picture that shows the necessary atomic orbitals and their overlap to form ethane (C2H6).

Draw a picture that shows the necessary atomic orbitals and their overlap to form water.

Practice with conceptual checkpoint 1.19


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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


Consider ethene (ethylene).

Each carbon in ethene must bond to three other atoms, so only three hybridized atomic orbitals are needed

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


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

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


The sp2 atomic orbitals overlap to form sigma () bonds

Sigma bonds provide maximum HEAD-ON overlap

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


The unhybridized p orbitals in ethene form pi () bonds, SIDE-BY-SIDE overlap

Practice with conceptual checkpoint 1.20


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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


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

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals

Why is sp2 hybridization not appropriate for methane (CH4)?

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


Consider ethyne (acetylene).
Each carbon in ethyne must bond to two other atoms, so only two hybridized atomic orbitals are needed

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


The sp atomic orbitals overlap HEAD-ON to form sigma () bonds while the unhybridized p orbitals overlap SIDEBY-SIDE to form pi bonds Practice with skill builder 1.7

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


Which should be stronger, a pi bond or a sigma bond? WHY?

Which should be stronger, an sp3 sp3 sigma bond overlap or an sp sp sigma bond overlap?

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Klein, Organic Chemistry 1e

1.9 Hybridized Atomic Orbitals


Explain the different strengths and lengths below.

Practice with conceptual checkpoint 1.24

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Klein, Organic Chemistry 1e

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

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Klein, Organic Chemistry 1e

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

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Klein, Organic Chemistry 1e

1.10
Methane has 4 equal bonds, so the bond angels are equal

3 sp

Geometry
The bond angels in oxygen are even smaller, why?

For any sp3 hybridized atom, the 4 valence electron pairs will form a tetrahedral electron group geometry
How does the lone pair of ammonia affect its geometry?

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Klein, Organic Chemistry 1e

1.10

3 sp

Geometry

The molecular geometry is different from the electron group geometry. HOW?

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Klein, Organic Chemistry 1e

1.10

2 sp

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?

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Klein, Organic Chemistry 1e

1.10

2 sp

Geometry

How many electrons are in Borons unhybridized p orbital? Does this geometry follow VSEPR theory?

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Klein, Organic Chemistry 1e

1.10

2 sp

Geometry

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

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Klein, Organic Chemistry 1e

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

CO2

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Klein, Organic Chemistry 1e

1.10 Geometry Summary


Practice with skill builder 1.8

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Klein, Organic Chemistry 1e

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 + and - 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
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Klein, Organic Chemistry 1e

1.11 Molecular Polarity


Lets consider the dipole of CH3Cl Dipole moment () = charge (e) x distance (d)
Plug in the charge and distance

= (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)

= 1.87 x 10-18 esu cm


Convert to debye

= 1.87 D
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Klein, Organic Chemistry 1e

1.11 Molecular Polarity


What would the dipole moment be if CH3Cl were 100% ionic? = charge (e) x distance (d)
Plug in the charge and distance

= (4.80 x 10-10 esu) x (1.772 x 10-8 cm)


The full charge of an electron is plugged in

= 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?
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Klein, Organic Chemistry 1e

1.11 Molecular Polarity


Check out the polarity of come other common bonds

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Klein, Organic Chemistry 1e

1.11 Molecular Polarity


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

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Klein, Organic Chemistry 1e

1.11 Molecular Polarity


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

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Klein, Organic Chemistry 1e

1.11 Molecular Polarity


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

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Klein, Organic Chemistry 1e

1.11 Molecular Polarity

Practice with skill builder 1.9


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Klein, Organic Chemistry 1e

1.11 Molecular Polarity

Explain why the dipole moment for pentane = 0 D


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Klein, Organic Chemistry 1e

1.12 Intermolecular Forces


Many properties such as solubility, boiling point, density, state of matter, melting point, etc. are affected by the attractions BETWEEN molecules Neutral molecules (polar and nonpolar) are attracted to one another through
Dipole-dipole interactions Hydrogen bonding Dispersion forces (a.k.a. London forces or fleeting dipoledipole forces)

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Klein, Organic Chemistry 1e

1.12 Dipole-Dipole
Dipole-dipole forces result when polar molecules line up their opposite charges. Note acetones permanent dipole results from the difference in electronegativity between C and O The dipole-dipole attractions BETWEEN acetone molecules affects acetones boiling and melting points. HOW?

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Klein, Organic Chemistry 1e

1.12 Dipole-Dipole
Why do isobutylene and acetone have such different MP and BPs?

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Klein, Organic Chemistry 1e

1.12 Hydrogen Bonding


Hydrogen bonds are an especially strong type of dipoledipole attraction Hydrogen bonds are strong because the partial + and charges are relatively large Why are the partial charges in the H-bonding examples below relatively large?

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Klein, Organic Chemistry 1e

1.12 Hydrogen Bonding


Only when a hydrogen shares electrons with a highly electronegative atom (O, N, F, or Cl) will it carry a large partial positive charge The large + on the H atom can attract large charges on other molecules Even with the large partial charges, H-bonds are still about 20 times weaker than covalent bonds Compounds with H atoms that are capable of forming Hbonds are called protic

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Klein, Organic Chemistry 1e

1.12 Hydrogen Bonding


Which of the following solvents are protic (capable of Hbonding), and which are not? Acetic acid

Diethyl ether Methylene chloride (CH2Cl2)

Dimethyl sulfoxide
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Klein, Organic Chemistry 1e

1.12 Hydrogen Bonding


Explain why the following isomers have different boiling points

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Klein, Organic Chemistry 1e

1.12 London Dispersion Forces


If two molecules are nonpolar (dipole = 0 D), will they attract one another?
YES! HOW?

Nonpolar molecules normally have their electrons (-) spread out evenly around the nuclei (+) completely balancing the charge However, the electrons are in constant random motion within their MOs

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Klein, Organic Chemistry 1e

1.12 London Dispersion Forces


The constant random motion of the electrons in the molecule will sometimes produce an electron distribution that is NOT evenly balanced with the positive charge of the nuclei Such uneven distribution produces a temporary dipole, which can induce a temporary dipole in a neighboring molecule

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Klein, Organic Chemistry 1e

1.12 London Dispersion Forces


The result is a fleeting attraction between the two molecules

Such fleeting attractions are generally weak. But like any weak attraction, if there are enough of them, they can add up to a lot
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Klein, Organic Chemistry 1e

1.12 London Dispersion Forces


The greater the surface area of a molecule, the more temporary dipole attractions are possible Consider the feet of Gecko. They have many flexible hairs on their feet that maximize surface contact
The resulting London dispersion forces are strong enough to support the weight of the Gecko

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Klein, Organic Chemistry 1e

1.12 London Dispersion Forces


Explain why molecules with more mass generally have higher boiling points

Practice with skill builder 1.10


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Klein, Organic Chemistry 1e

1.12 London Dispersion Forces


Explain why more highly branched molecules generally have lower boiling points

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Klein, Organic Chemistry 1e

1.13 Solubility
We use the principle, like-dissolves-like Polar compounds generally mix well with other polar compounds
If the compounds mixing are all capable of H-bonding and/or strong dipole-dipole, then there is no reason why they shouldnt mix

Nonpolar compounds generally mix well with other nonpolar compounds


If none of the compounds are capable of forming strong attractions, then no strong attractions would have to be broken to allow them to mix

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Klein, Organic Chemistry 1e

1.13 Solubility
We know it is difficult to get a polar compound (like water) to mix with a nonpolar compound (like oil)
We cant use just water to wash oil off our dirty cloths

To remove nonpolar oils, grease, and dirt, we need soap

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Klein, Organic Chemistry 1e

1.13 Solubility
Soap molecules organize into micelles in water, which form a nonpolar interior to carry away dirt.

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Klein, Organic Chemistry 1e

1.13 Solubility
Which attraction is generally stronger?
The attraction between a permanent dipole and an induced dipole or The attraction between a temporary dipole and an induced dipole

Which attraction is generally stronger?


The attraction between a polar molecule and a nonpolar molecule or The attraction between two nonpolar molecules?
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Klein, Organic Chemistry 1e

1.13 Solubility
Why wont a nonpolar compound readily dissolve in water? Is it because the water molecules repel the nonpolar molecules?

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