Organic Chemistry I Tutorials with Worksheets

Video Lectures

Displaying all 210 video lectures.
Lecture 1
Organic molecules in your everyday life
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Organic molecules in your everyday life
Why do we take an entire year learning about Organic chemistry? What makes Ochem so special? Let’s find out.
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Lecture 2
What is an organic molecule?
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What is an organic molecule?
Organic Molecule: Any molecule that contains carbon bonded to hydrogen. Hydrocarbon: Any molecule that contains only carbon and hydrogen, and nothing else.
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Lecture 3
The difference between atomic numbers and atomic mass
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The difference between atomic numbers and atomic mass
Been awhile since Chem 1? Let’s cover some of the essentials from general chemistry that you’ll need for this course.
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Lecture 4
Shells, orbitals and types of ions
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Shells, orbitals and types of ions
Shell: Region of space that electrons orbit around the nucleus in. Orbital: Region of space within a shell with exactly enough space for two electrons. Ion: An atom that has an unequal number of electrons and protons.
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Lecture 5
3 rules about orbitals you need to know
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3 rules about orbitals you need to know
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Lecture 6
The probability of finding electrons in a given place
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The probability of finding electrons in a given place
This video deals with the basics of quantum mechanics. Don’t worry too much about it, but this is some good general information.
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Lecture 7
What’s the difference between sigma and pi bonds
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What’s the difference between sigma and pi bonds
When atomic orbitals interfere constructively with each other, they increase the chances of finding electrons between nuclei, forming what we call a bond.
What's the difference between sigma and pi bonds?
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Lecture 8
What’s the difference between atomic and molecular orbitals
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What’s the difference between atomic and molecular orbitals
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Lecture 9
Single bonds, double bonds, and triple bonds
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Single bonds, double bonds, and triple bonds
There’s some simple facts about different types of bonds that could show up on your exam. Here’s a really nice summary for you.
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Lecture 10
How Nobel gases are related to the octet rule
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How Nobel gases are related to the octet rule
This might be the most important rule in all of undergraduate chemistry! Let’s start from the beginning and go from there.
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Lecture 11
The most important parts of the periodic table for organic chemistry
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The most important parts of the periodic table for organic chemistry
Science-y Version: Helium would have to fill an anti-bonding molecular orbital in order to bond to itself, which undoes the extra stability provided by the filled bonding orbital, so it has no reason to make a bond. Basic Version: Nobel gases don’t like to bond to anything!
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Lecture 12
The octet rule
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The octet rule
Octet electrons is the name we give to ALL electrons that surround an atom. These help the atom reach its Nobel gas configuration.
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Lecture 13
What is a valance electron?
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What is a valance electron?
Just because an atom satisfies its octet doesn’t mean that it is stable. We also have to consider valance electrons. Sounds familiar? Let’s look into what those are.
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Lecture 14
What is the difference between valance and octet electrons?
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What is the difference between valance and octet electrons?
All of these carbons satisfy their octet, but only one of them is actually stable. The others suck. How can we tell which one will be stable?
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Lecture 15
Calculating formal and net charge
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Calculating formal and net charge
We use our knowledge of valance electrons to determine what the formal charge of the molecule will be.
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Lecture 16
Calculate the formal charges of ALL atoms
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Calculate the formal charges of ALL atoms
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Lecture 17
How bondline is different from Lewis Structures
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How bondline is different from Lewis Structures
Since we are going to be drawing A LOT of molecules over the next year, it makes sense to find an easier way to draw them. Hence, I now present to you :::drumroll::: the bondline structure! *Also known as skeletal structure or line-angle structure.
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Lecture 18
How to use Organic Chemistry to make Lewis Structures easier
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How to use Organic Chemistry to make Lewis Structures easier
Drawing Lewis Structures is something we learned how to do in Gen Chem. Nothing has changed since then, but now since we know about bonding preferences, that makes it a lot easier.
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Lecture 19
How to interpret condensed structures
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How to interpret condensed structures
What if you want to describe a molecule, but you have nothing but a keyboard? (No fancy pictures or drawings). This is was actually a big dilemma in the chemistry world, which is why we now have condensed structure.
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Lecture 20
The difference between saturated and unsaturated molecules
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The difference between saturated and unsaturated molecules
Hydrocarbons fall into two categories: Saturated and Unsaturated- and both of these terms describe the number of hydrogens that carbon is bonded to.
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Lecture 21
What index of hydrogen deficiency is
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What index of hydrogen deficiency is
IHD is also known as the Degree of Unsaturation. Basically the IHD is an easy way for us to compare how unsaturated a molecule is compared to another.
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Lecture 22
How to use IHD with molecular formula
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How to use IHD with molecular formula
Unfortunately, the structure of a compound will not always be drawn for us. In that case, we use the following technique.
If your professor taught you a different method, that’s fine! Whatever helps you get the right answer.
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Lecture 23
What is a constitutional isomer?
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What is a constitutional isomer?
“How are the following two molecules related to each other?”
Does this sound familiar? This is one of the most important questions you will have to answer in Organic Chemistry 1.
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Lecture 24
The rules you need for resonance
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The rules you need for resonance
Resonance is used to represent all the different ways that identical molecules can distribute electrons.
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Lecture 25
Common ways to move arrows in resonance
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Common ways to move arrows in resonance
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Lecture 26
How to determine which structure is most stable
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How to determine which structure is most stable
Often one of the resonance structures will be more stable, so it will contribute to the hybrid more than the others. Use the octet rule and electronegativity trends to determine the best placement of charges. (i.e. Fluorine is more stable with a negative charge than oxygen).
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Lecture 27
How carbon creates 4 partially-filled orbitals
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How carbon creates 4 partially-filled orbitals
Aufbau Principle predicts that carbon would have two partially filled 2p orbitals, suggesting that carbon could only make 2 bonds. However, carbon actually makes 4 bonds. How do we explain this?
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Lecture 28
Using bond sites to predict hybridization
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Using bond sites to predict hybridization
A bond site is the name that we give to any lone pair or atom attached to the hybridized atom. The number of bond sites is what determines the hybridization of the molecule.
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Lecture 29
Molecular Geometry Explained
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Molecular Geometry Explained
Hybridization describes orbitals, but molecular geometry describes the shape of the atom.
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Lecture 30
How to tell the difference between ionic, polar and covalent bonds
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How to tell the difference between ionic, polar and covalent bonds
All bonds are not created equal. Some bonds perfectly share their electrons, and others barely share them at all. A dipole moment is the mathematical expression that describes this disbalance.
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Lecture 31
How IMFs are related to melting and boiling points
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How IMFs are related to melting and boiling points
Now that we understand how bonds keep atoms together, the next question is, what force keeps molecules together? Do they bond to each other as well? Let’s take a look.
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Lecture 32
How hydrogen bonding works
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How hydrogen bonding works
Hydrogens attached to small, highly electronegative atoms can hydrogen bond. Namely N, O and F.
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Lecture 33
How dipole-dipole forces work
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How dipole-dipole forces work
We like to call this the net dipole force because it’s only present when the molecule has a net dipole.
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Lecture 34
How Van der Waals forces work
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How Van der Waals forces work
Van der Waals Forces is also known as London Dispersion Forces or Dipole-Induced Dipole Forces.
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Lecture 35
Understanding “like dissolves like”
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Understanding “like dissolves like”
Only one rule to know here: Like polarity dissolves like polarity.
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Lecture 36
Introducing common solvents and other molecules in organic chemistry
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Introducing common solvents and other molecules in organic chemistry
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Lecture 37
Why we need functional groups
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Why we need functional groups
We can group millions of different molecules into families of similar functionality.
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Lecture 38
Recognizing different types of hydrocarbons
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Recognizing different types of hydrocarbons
All carbon groups, regardless of size, can be symbolized using an –R group. When an alkane is attached to a greater carbon chain, it is given a –yl suffix. An alkane turns into an alkyl group.
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Lecture 39
How to assign degrees to carbons and hydrogens
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How to assign degrees to carbons and hydrogens
Carbons are given a “degree” based on how many other carbons they are attached to. Degrees are expressed as primary, secondary, tertiary and quaternary (1°, 2°, 3°, 4°). Hydrogens possess the SAME degree as the carbon they are attached to.
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Lecture 40
Recognizing alkyl halides
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Recognizing alkyl halides
Condensed Structure = -RX. The degree of the alkyl halide is determined the same exact way as hydrogen.
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Lecture 41
How to recognize alcohols, amines and ethers
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How to recognize alcohols, amines and ethers
Carbonyls are C=O bonds within a molecule. First we’ll learn about common functional groups that don’t contain these.
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Lecture 42
How to recognize carboxylic acids, amides and esters
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How to recognize carboxylic acids, amides and esters
As you see, these functional groups are similar to the other ones, but have different names due to the adjacent carbonyl.
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Lecture 43
The difference between aldehydes and ketones
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The difference between aldehydes and ketones
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Lecture 44
How to recognize nitriles
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How to recognize nitriles
Nitrile Condensed Structure = -CN
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Lecture 45
The difference between phenyl and benzyl groups
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The difference between phenyl and benzyl groups
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Lecture 46
Recognizing acyl chlorides and anhydrides
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Recognizing acyl chlorides and anhydrides
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Lecture 47
What you need to know about types of chemical reactions
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What you need to know about types of chemical reactions
Now you’re finally getting ready to start understanding types of chemical reactions. Oh joy!
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Lecture 48
Recognizing Acid-Base Reactions
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Recognizing Acid-Base Reactions
We’re gonna learn about 4 different types of chemical reactions. You don’t actually need to understand these! Just be able to recognize them for now.
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Lecture 49
How to tell if a molecule will be reactive or not
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How to tell if a molecule will be reactive or not
Stability and reactivity generally have an inverse relationship. If a molecule is unstable in some way, it will want to react! Here are the 4 signs we can look for that determine reactivity.
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Lecture 50
How to tell if charged molecules will react as nucleophiles or electrophiles
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How to tell if charged molecules will react as nucleophiles or electrophiles
Now that we know how to determine if molecules are reactive, we still don’t know HOW they will react! There are two major subtypes of reactivity that we’ll often use in Orgo 1 and 2.
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Lecture 51
How to tell if uncharged molecules will react as nucleophiles or electrophiles
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How to tell if uncharged molecules will react as nucleophiles or electrophiles
So that wasn’t so hard, but those were the easy cases. What if you have nucleophilic AND electrophilic regions on the same molecule? Is it possible to determine how it will react? Yes it is!
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Lecture 52
Learning the rules of electron movement
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Learning the rules of electron movement
Now we understand which molecules will want to react, and we are getting better at determining If they are nucleophiles or electrophiles, but how to they actually attack other molecules?
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Lecture 53
Why we need to break bonds sometimes
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Why we need to break bonds sometimes
So now we know how to make bonds. Do we ever have to break bonds? How do we know if we do or we don’t?
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Lecture 54
The Lewis definition of acids and bases
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The Lewis definition of acids and bases
The Lewis definition is the most general of the definitions that applies to all cases. It’s actually just another name for what we learned earlier as Nucleophiles and Electrophiles.
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Lecture 55
The Brønsted Lowry definition of acids and bases
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The Brønsted Lowry definition of acids and bases
The Brønsted-Lowry definition is a more specific definition that only applies to some acids and bases. In this definition, electrons don’t matter- we only look at protons.
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Lecture 56
Equilibrium constant and conjugates
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Equilibrium constant and conjugates
When determining how acids and bases react together, it important to understand the concepts of conjugates and Ke.
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Lecture 57
Why we use pKa instead of pH
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Why we use pKa instead of pH
Now that we understand what an acid is, we need a method of quantifying which acids are stronger and which are weaker. pH doesn’t work for this, let me explain why.
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Lecture 58
The relationship between equilibrium constant and pKa
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The relationship between equilibrium constant and pKa
The Ka (dissociation constant) describes the tendency of a molecule to break apart. In the case of acids, that specifically means donating protons, which is exactly what we are interested in knowing!
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Lecture 59
The pH scale vs the pKa scale
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The pH scale vs the pKa scale
The pH and pKa scales really are completely different. Pardon my French! pKas are obviously something I’m really passionate about.
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Lecture 60
The 12 pKa values you want to memorize because they're important!
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The 12 pKa values you want to memorize because they're important!
Here is a list of the MINIMUM number of pKa values to memorize. By the time you get to your exam, you should at least know these values.
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Lecture 61
The 3 steps for determining the direction of acid and base equilibrium
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The 3 steps for determining the direction of acid and base equilibrium
The holy grail of acid-base chemistry is to be able to draw the mechanism and predict the equilibrium for an acid-base reaction. Believe it or not, you’re ready to do this.
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Lecture 62
Why we need factors affecting acidity and when to use them
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Why we need factors affecting acidity and when to use them
There are two situations in particular that making predicting equilibrium challenging: you don’t know the pKas of the acids, and the pKas for the acid and the conjugate acid are both the same.
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Lecture 63
Understanding the Element Effect
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Understanding the Element Effect
This effect describes the way different atoms donate protons. For example C-H vs. N-H.
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Lecture 64
Understanding the Inductive Effect
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Understanding the Inductive Effect
This effect describes the way that electronegative atoms that are NOT CONNECTED to the acidic proton make the conjugate base more stable.
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Lecture 65
Understanding resonance effects Which of the following –OH groups would be more acidic and why?
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Understanding resonance effects Which of the following –OH groups would be more acidic and why?
If a conjugate base is able to make a resonance structure, it will be more stable.
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Lecture 66
Understanding hybridization effects
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Understanding hybridization effects
The higher the %s-character of the conjugate base, the more stable it will be.
Recall, %s-character = (s-orbitals)/(total hybrid orbitals) x 100. Aka, sp3 = ¼ = 25% s-character.
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Lecture 67
The different parts of an IUPAC name
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The different parts of an IUPAC name
In chemistry, every single molecule needs a unique name. We can’t have two molecules with the same name or that would get super confusing! For this, we use IUPAC nomenclature.
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Lecture 68
Learning Alkane Prefixes up to 12 Carbons in Length
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Learning Alkane Prefixes up to 12 Carbons in Length
Memorizing sucks, I get it. But this is something you’re just gonna have to remember. Not all professors will make you memorize all 12- check with your professor to figure out how many you need to know!
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Lecture 69
Naming the root chain
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Naming the root chain
Remember, if there is a TIE between two chains of equal length, go with the chain that gives the MOST substituents!
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Lecture 70
How to determine the direction of the root chain
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How to determine the direction of the root chain
Now we know the length of the root chain, but nothing else! We need to determine which carbon gets the “1” location.
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Lecture 71
How to identify and locate branches (substituents)
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How to identify and locate branches (substituents)
So we know the length and direction of the root chain, which is great. But if there are ANY branches on this chain, we need to name those too. P.S. The term “substituent” is just a nerdy word for a “branch”.
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Lecture 72
Proper name ordering and punctuation
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Proper name ordering and punctuation
Now we have all the pieces we need to name most alkanes, but we need to work on our formatting! Chemists are surprisingly analytical making sure all your commas and numbers are in the right place.
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Lecture 73
Understanding Non IUPAC Substituents
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Understanding Non IUPAC Substituents
IUPAC naming is awesome because it’s pretty easy to master. But unfortunately there are some non-IUPAC names we need to know for this course. These apply mostly to weird looking substituents.
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Lecture 74
How to find the root name for cycloalkanes
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How to find the root name for cycloalkanes
Ringed structures are easy to name, you just need to use a new prefix (aka –cyclo)!
Hint: Benzene and a cyclohexane are NOT the same thing. Remember, benzene has double bonds in it!
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Lecture 75
Why it is okay to omit a single location for monocyclics
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Why it is okay to omit a single location for monocyclics
If you only have one substituent on your ring, the numerical location is unnecessary!
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Lecture 76
What is a bicyclic molecule?
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What is a bicyclic molecule?
Bicyclics are also forms of cycloalkanes, but since they are not monocycles, they have completely different rules for naming!
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Lecture 77
The two types of bicyclic molecules
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The two types of bicyclic molecules
Bicyclic rings possess multiple ringed systems within the same molecule.
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Lecture 78
How to name a bridged bicyclic
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How to name a bridged bicyclic
The bridgehead atom (one of the circled ones) must always be in the “1” position. The name is formatted as bicyclo[ringsize1.ringsize2.ringsize3]alkane.
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Lecture 79
How to name alkyl halides
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How to name alkyl halides
Now it’s time to start naming functional groups! We’ll start with alkyl halides because they are some of the easiest to name.
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Lecture 80
How to name alkenes and alkynes
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How to name alkenes and alkynes
When alkanes contain double or triple bonds, that totally changes the way we name the molecule. Alkenes and alkynes are named as modifiers, meaning we add suffix modifiers to the root chain.
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Lecture 81
How to name alcohols
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How to name alcohols
Like double and triple bonds, –OH groups change the reactivity of an alkane. So these are considered functional groups, called alcohols.
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Lecture 82
Old School vs. New School Naming
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Old School vs. New School Naming
The biggest takeaway here is just to remember that having more than one location in front of your root name is always a mistake! Place at least one of the locations within the root (or even all of them).
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Lecture 83
How to name different types of double bonds or rings
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How to name different types of double bonds or rings
Since double bonds and rings can’t rotate, we need different names for the different arrangements they can create.
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Lecture 84
Why we need to use the EZ naming system
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Why we need to use the EZ naming system
The cis/trans nomenclature system is awesome, but it breaks down with multisubstituted alkenes. The E/Z naming system allows us to name tri- and tetra- substituted alkenes.
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Lecture 85
What does E and Z stand for
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What does E and Z stand for
Using the periodic table to assign priorities, trans = E, and cis = Z.
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Lecture 86
Understanding what a conformer is
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Understanding what a conformer is
As we’ve learned before, single bonds have the ability to freely rotate, meaning that we have to get used to seeing multiple arrangements of single bonds and understanding that they are all the same thing.
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Lecture 87
How sigma bond rotation is visualized
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How sigma bond rotation is visualized
We use Newman projections to visualize the rotations of conformers. Some are more stable than others.
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Lecture 88
The energy states of 3 different Newman Projections
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The energy states of 3 different Newman Projections
The dihedral angle (theta), is equal to the angle between the two largest groups on either side of the projection.
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Lecture 89
Six Steps to Drawing Newman Projections Step 1
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Six Steps to Drawing Newman Projections Step 1
Worked Example: Draw the most energetically favorable Newman Projection for CH3CH2CH2CH2CH3 down the C2 – C3 bond
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Lecture 90
Six Steps to Drawing Newman Projections Step 2
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Six Steps to Drawing Newman Projections Step 2
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Lecture 91
Six Steps to Drawing Newman Projections Step 3
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Six Steps to Drawing Newman Projections Step 3
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Lecture 92
Six Steps to Drawing Newman Projections Step 4
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Six Steps to Drawing Newman Projections Step 4
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Lecture 93
Six Steps to Drawing Newman Projections Step 5
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Six Steps to Drawing Newman Projections Step 5
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Lecture 94
Six Steps to Drawing Newman Projections Step 6
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Six Steps to Drawing Newman Projections Step 6
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Lecture 95
4 Values You Should Memorize
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4 Values You Should Memorize
Sometimes we’ll be asked to actually calculate the amount of energy a Newman Projection “spends” while rotating.
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Lecture 96
Understanding Heat of Combustion
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Understanding Heat of Combustion
We can use an instrument called a calorimeter to determine how much potential energy is stored in molecules.
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Lecture 97
Shape and strain make alkanes unstable
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Shape and strain make alkanes unstable
Strain is a super general word. So now let’s go more into specifics of the types of strain you need to recognize.
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Lecture 98
What is angle strain?
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What is angle strain?
The ideal bond angle for sp3 hybirdized carbon is 109.5°, so the more we deviate from that number, the more unstable the angle will be! (Aka cyclopropane sucks).
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Lecture 99
What is torsional strain?
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What is torsional strain?
Torsional strain increases with the number of eclipsing hydrogens in a molecule. Some of these rings are so small they can’t twist to prevent these interactions, which makes them unstable.
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Lecture 100
What is a chair conformation?
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What is a chair conformation?
Instead of being planar, cyclohexane twists into something called a chair conformation to reduce angle and torsional strain.
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Lecture 101
How chairs flip from one conformation to another
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How chairs flip from one conformation to another
In order to flip from one chair to another, the cyclohexane must first pass through a boat conformation (not stable due to flagpole interactions of hydrogens!).
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Lecture 102
How to draw chairs
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How to draw chairs
Before we can really understand chair conformations, we have to practice drawing them! These tricky little suckers can be hard to get right.
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Lecture 103
How to distinguish cis from trans
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How to distinguish cis from trans
Cis or trans is based on whether the groups are facing the same face (top or bottom) of the ring—it has nothing to do with the axial and equatorial positions!
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Lecture 104
Axial or Equatorial: Which position is better?
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Axial or Equatorial: Which position is better?
This is the #1 thing you need to know about cyclohexane. So let’s get right into it.
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Lecture 105
The 3 important factors when drawing chairs
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The 3 important factors when drawing chairs
How do you know you're drawing your chairs right? There are only 3 things that you have to keep track of when you draw a chair: Distance between groups, Cis vs. Trans, and Equatorial Preference.
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Lecture 106
How to determine the stability of a declin
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How to determine the stability of a declin
If you liked bicyclic molecules, you’ll love declins. They are just fused bicyclic cyclohexanes. As is hopefully evident from the drawings, trans-declins are more stable than cis-declins.
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Lecture 107
Draw the following declin as a chair conformation in the most stable conformation
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Draw the following declin as a chair conformation in the most stable conformation
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Lecture 108
Determining when molecules are different
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Determining when molecules are different
Isomers are terms used to describe relationships between similar molecules.
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Lecture 109
Determining when molecules are constitutional isomers
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Determining when molecules are constitutional isomers
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Lecture 110
What is chirality?
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What is chirality?
Chiral is the chemistry term we use to describe objects whose mirror image is different from the original.
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Lecture 111
How and when to use the internal line of symmetry test
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How and when to use the internal line of symmetry test
The simplest test for chirality is symmetry. If a molecule has an internal line of symmetry, it is achiral.
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Lecture 112
What is a stereocenter?
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What is a stereocenter?
The gold standard chirality test for almost all molecules involves finding stereocenters.
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Lecture 113
The difference between chiral and trigonal centers
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The difference between chiral and trigonal centers
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Lecture 114
Why stereoisomers need their own naming system
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Why stereoisomers need their own naming system
According to IUPAC protocol, each molecule must have a unique, unambiguous name – even stereoisomers.
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Lecture 115
R and S Naming - Step 1
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R and S Naming - Step 1
Step 1: Assign priorities to the four atoms on the chiral center according to their atomic mass on the periodic table.
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Lecture 116
R and S Naming - Step 2
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R and S Naming - Step 2
Step 2: When there is a tie between atomic weights, compare the next set of adjacent atoms (playoffs!)
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Lecture 117
R and S Naming - Step 3
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R and S Naming - Step 3
Step 3: Double bonds count twice. Triple bonds count three times
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Lecture 118
R and S Naming - Step 4
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R and S Naming - Step 4
Step 4: If the last priority group is in the back, then trace a path from highest to lowest priority
— Clockwise = R, Counterclockwise = S — Always Ignore group 4
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Lecture 119
R and S Naming - Step 5
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R and S Naming - Step 5
Step 5: If the last priority group is NOT in the back, swap that group with the group that is on the dash. Trace path as always, but this time swap the sign since you swapped groups.
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Lecture 120
Using chiral centers to predict types of stereoisomers
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Using chiral centers to predict types of stereoisomers
We can use our knowledge of chiral centers to predict what types of stereoisomers molecules will make.
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Lecture 121
How to predict the total number of stereoisomers
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How to predict the total number of stereoisomers
Follow the 2n (n = stereocenters) rule to predict total number of possible stereoisomers. Note: Remember that stereocenters include both chiral centers and trigonal centers!
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Lecture 122
Recognizing chiral molecules with zero chiral centers
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Recognizing chiral molecules with zero chiral centers
These are exceptions to the rule: molecules that contain no chiral centers yet are chiral due to their inability to freely rotate.
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Lecture 123
Determining if allenes are chiral or not
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Determining if allenes are chiral or not
Imagine that the allene is a big double bond. If it is able to form E or Z isomers, it is chiral.
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Lecture 124
Determining if substituted biphenyls are chiral or not
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Determining if substituted biphenyls are chiral or not
Must meet two criteria to be chiral: all substituents are in the ortho- position, and none of the rings have two of the same group on them.
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Lecture 125
Defining meso compounds
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Defining meso compounds
Another exception to the rule, these are compounds that remain achiral even though they have chiral centers!
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Lecture 126
The 3 rules of meso compounds
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The 3 rules of meso compounds
A compound will be meso if it meets the following 3 criteria: it has 2 or more chiral centers, it is atomically symmetrical, and an even number of chiral centers have opposite configuration to each other.
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Lecture 127
Three types of disubstituted cycloalkanes
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Three types of disubstituted cycloalkanes
Since these molecules come up often in exams, it’s a good idea to just memorize a few simple rules for them.
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Lecture 128
Cis-1,2-Disubstituted Cyclohexane A controversial exception
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Cis-1,2-Disubstituted Cyclohexane A controversial exception
Because cyclohexane has axial and equatorial positions, some professors will have different definitions of whether this is chiral or not. Textbook Answer (correct) = Achiral. Some wacky professors = Chiral.
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Lecture 129
Different atoms or different connectivity
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Different atoms or different connectivity
One of the most frequently asked exam questions in this chapter is: “What is the relationship between the following two molecules?”. We’re going to learn a systematic method to solve these questions.
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Lecture 130
Same atoms, same connectivity, 0 chiral centers
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Same atoms, same connectivity, 0 chiral centers
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Lecture 131
Same atoms, same connectivity, 1 chiral center
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Same atoms, same connectivity, 1 chiral center
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Lecture 132
Same atoms, same connectivity, 2 or more chiral centers
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Same atoms, same connectivity, 2 or more chiral centers
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Lecture 133
Same atoms, same connectivity, 1 or more trigonal centers
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Same atoms, same connectivity, 1 or more trigonal centers
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Lecture 134
When to use R and S, when you don’t have to
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When to use R and S, when you don’t have to
Solving for R and S on every single molecule can be a headache. If the molecule hasn’t been rotated, feel free to use “different or same” as a surrogate for R and S.
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Lecture 135
Introduction to different projections
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Introduction to different projections
There are several common projections used to visualize molecules in different perspectives.
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Lecture 136
How to convert Fischer projections into bondline structures
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How to convert Fischer projections into bondline structures
We will need to know how to convert these into bondline so that we can analyze them. Make a caterpillar, then rotate every other bond.
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Lecture 137
R and S rule for Fischer Projections
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R and S rule for Fischer Projections
Determine location of lowest priority group: if vertical, chirality is as it looks, if horizontal, chirality is flipped.
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Lecture 138
Specific rotation vs observed rotation
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Specific rotation vs observed rotation
One of the special features of chiral molecules is that they are able to rotate plane-polarized light. Unfortunately, this means that now professors have an excuse to ask you math problems.
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Lecture 139
How to calculate enantiomeric excess
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How to calculate enantiomeric excess
Specific rotation [α] is the rotation that 100% pure enantiomers produce. Opposite enantiomer = opposite rotation. Racemic: a perfect 1:1 ratio of enantiomers. Scalemic: a non-1:1 ratio of enantiomers.
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Lecture 140
How to solve for the percentage of each enantiomer
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How to solve for the percentage of each enantiomer
Sometimes professors will ask us to solve for exact the percentage of each enantiomer in solution. For that we’ll need some new equations.
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Lecture 141
Breaking down the different terms of the Gibbs Free Energy equation
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Breaking down the different terms of the Gibbs Free Energy equation
Time for Gibbs Free Energy, the most important equation for understanding reaction favorability! It’s going to be important that we understand the significance of all the terms of this equation.
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Lecture 142
How to calculate enthalpy using bond dissociation energies
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How to calculate enthalpy using bond dissociation energies
Bond dissociation energies describe the strength of chemical bonds. They can be determined experimentally. We’ll need some basic math for this section.
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Lecture 143
Explaining what entropy is
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Explaining what entropy is
If a reaction is exothermic, shouldn’t that be enough to determine favorability? Actually, no! Even if a reaction is highly exothermic, the level of order it requires may make it statistically improbable.
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Lecture 144
Defining the Hammond Postulate
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Defining the Hammond Postulate
The Hammond-Postulate more accurately describes what transition states look like. Paraphrased version: “Transition states most closely resemble the species with the highest energy.”
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Lecture 145
Determining Carbocation Stability
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Determining Carbocation Stability
Now we’re going to discuss the most important intermediate of all organic chemistry, the carbocation.
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Lecture 146
Understanding why carbocations shift
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Understanding why carbocations shift
Carbocations will rearrange to an adjacent, more stable possible if possible. These have different names based on which atoms are rearranging.
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Lecture 147
Remembering general patterns of reactions
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Remembering general patterns of reactions
We can use reactions we’ve learned in the past (particularly acid-base reactions) to understand substitution. In fact, substitution is just a category of Lewis acid-base reactions!
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Lecture 148
Nucleophiles and Electrophiles can react in Bronsted Lowry Reactions
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Nucleophiles and Electrophiles can react in Bronsted Lowry Reactions
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Lecture 149
Nucleophiles and Electrophiles can react in Lewis Acid Base Reactions
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Nucleophiles and Electrophiles can react in Lewis Acid Base Reactions
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Lecture 150
How to use the factors affecting acidity to predict leaving group ability
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How to use the factors affecting acidity to predict leaving group ability
The favorability of many reactions depends on the ability of the leaving group to be stable after it gains a negative charge. That’s because this is the same exact way we determine conjugate base stability.
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Lecture 151
Drawing the SN2 Mechanism
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Drawing the SN2 Mechanism
Time to start learning about some of the most important reactions in all of organic chemistry. In fact, you’re never allowed to forget this one!
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Lecture 152
Drawing the SN1 Mechanism
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Drawing the SN1 Mechanism
The SN1 mechanism is similar to SN2 in that you get a substitution product, but the path to get there is completely different. It’s important that we understand how it’s different from SN2.
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Lecture 153
Why highly substituted leaving groups favor SN1
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Why highly substituted leaving groups favor SN1
The slow step of this mechanism is the formation of a carbocation intermediate. These types of intermediates are unstable, so anything that we can do to stabilize them will help them form faster.
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Lecture 154
How do we predict if the mechanism is SN1 or SN2
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How do we predict if the mechanism is SN1 or SN2
How can we tell which mechanism to use? This question will get more complicated unfortunately, but for now we can use the following factors to answer this question.
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Lecture 155
Drawing the E2 Mechanism
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Drawing the E2 Mechanism
Time to discuss the most complicated mechanism of the bunch, E2. It’s an awesome reaction, but there are a few extra details we’re gonna have to keep track of!
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Lecture 156
The number of unique β carbons helps predict the number of possible products
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The number of unique β carbons helps predict the number of possible products
In order to predict E2 products, we’ll have to get good at recognizing how many different and eligible β-hydrogens exist.
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Lecture 157
The number of unique β carbons in an anti-coplanar arrangement predicts the total number of products
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The number of unique β carbons in an anti-coplanar arrangement predicts the total number of products
Now we know how to find β-hydrogens, but it turns out that E2 reactions require an anti-coplanar arrangement (also called anti-periplanar) in order for the orbitals to overlap and create a new pi bond.
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Lecture 158
Drawing the E1 Mechanism
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Drawing the E1 Mechanism
The E1 mechanism is similar to E2 in that you get a substitution product, but the path to get there is completely different. It’s important that we understand how it’s different from E2.
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Lecture 159
Understanding the properties of E1
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Understanding the properties of E1
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Lecture 160
General format of reactions and how to interpret solvents
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General format of reactions and how to interpret solvents
Solvents are the mostly inert compounds that provide a medium for the reaction to take place in.
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Lecture 161
The difference between protic vs. aprotic solvents
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The difference between protic vs. aprotic solvents
Aprotic Solvents are solvents that cannot display hydrogen-bonding. Protic Solvents are solvents that display hydrogen-bonding (this stabilizes carbocations, but hinders nucleophiles).
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Lecture 162
The 3 important leaving groups to know
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The 3 important leaving groups to know
At this point, the only leaving group you are really familiar with is alkyl halides. It turns out there are 2 more you should definitely know about.
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Lecture 163
Overview of the flowchart
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Overview of the flowchart
Here is the best flowchart you’ll ever learn in your life. Seriously. When do you use this flowchart? Whenever you have a nucleophile and a GOOD leaving group.
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Lecture 164
How to predict SN2 and E2 mechanisms
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How to predict SN2 and E2 mechanisms
In general, the left side of the flowchart predicts SN2 /E2 mechanisms, and the right side predicts SN2/E2 mechanisms, but there are exceptions.
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Lecture 165
How to predict SN1 and E1 mechanisms
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How to predict SN1 and E1 mechanisms
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Lecture 166
Understanding trends of alkene stability
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Understanding trends of alkene stability
Not all alkenes were created equal. Like carbocations, alkenes are stabilized through a phenomenon called hyperconjugation.
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Lecture 167
Defining Zaitsev’s Rule
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Defining Zaitsev’s Rule
Elimination reactions often can yield multiple products. However, not all of these products will be of equal stability. Zaitsev’s Rule (also spelled Saytzeff’s Rule) helps us predict the major product.
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Lecture 168
Using a Free Energy Diagram to explain thermodynamic vs. kinetic products
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Using a Free Energy Diagram to explain thermodynamic vs. kinetic products
The Zaitsev product is also known as the thermodynamic product, since it is the one that releases the most free energy overall (most negative ΔG°).
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Lecture 169
The dehydrohalogenation mechanism
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The dehydrohalogenation mechanism
The elimination reaction is exactly what it sounds like. Use a base to take away (de-) one hydrogen and one halogen. Voila! We’ve got a double bond.
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Lecture 170
General features of double dehydrohalogenation
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General features of double dehydrohalogenation
When two equivalents of halide are present, bases can eliminate twice, creating alkynes as products.
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Lecture 171
Understanding how to convert terminal alkynes to alkynides
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Understanding how to convert terminal alkynes to alkynides
Now it’s time to introduce some of the most important nucleophiles in all of organic chemistry, alkynides.
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Lecture 172
Using double dehydrohalogenation to perform alkynide synthesis
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Using double dehydrohalogenation to perform alkynide synthesis
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Lecture 173
The definition of hydrogenation
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The definition of hydrogenation
Hydrogenation reactions are a subtype of reduction reactions that add hydrogens to double and triple bonds. These differ in the types of products made and the stereochemistry of the mechanism.
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Lecture 174
Using Catalytic hydrogenation or Wilkinson’s Catalyst to turn alkynes to alkanes
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Using Catalytic hydrogenation or Wilkinson’s Catalyst to turn alkynes to alkanes
Catalytic Hydrogenation or Wilkinson’s Catalyst: Alkane products
Stereochemistry: Syn Addition
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Lecture 175
Using Dissolving Metal Reduction or Lindlar’s Catalyst to turn alkynes to alkenes
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Using Dissolving Metal Reduction or Lindlar’s Catalyst to turn alkynes to alkenes
Dissolving Metal Reduction: Alkene products. Stereochemistry: Anti Addition.
Lindlar’s Catalyst: Alkene products. Stereochemistry: Syn Addition.
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Lecture 176
General features of acid catalyzed dehydration
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General features of acid catalyzed dehydration
For elimination to take place, you need a good leaving group. Alcohols are terrible leaving groups, but in the presence of acid, they can be converted into water, which is an amazing leaving group.
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Lecture 177
Dehydration of 1° alcohols The E2 Mechanism
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Dehydration of 1° alcohols The E2 Mechanism
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Lecture 178
Dehydration of 2° and 3° alcohols The E1 Mechanism
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Dehydration of 2° and 3° alcohols The E1 Mechanism
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Lecture 179
An extra note of caution with 1° alcohols
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An extra note of caution with 1° alcohols
This isn’t the case of 1° alcohols that can rearrange to 3° alcohols. Since the 1,2-rearrangement creates a super stable carbocation, the reaction will follow the E1 pathway.
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Lecture 180
General features of dehydration with phosphoryl chloride
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General features of dehydration with phosphoryl chloride
Another form of dehydration uses POCl3 to convert alcohol to a good leaving group.
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Lecture 181
Features of Addition Mechanisms
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Features of Addition Mechanisms
Addition reactions are ones in which 1 π-bond is broken and 2 new σ-bonds are formed. They are the opposite of elimination reactions (if you haven’t learned about these yet don’t worry).
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Lecture 182
How to add to asymmetrical double bonds
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How to add to asymmetrical double bonds
The general addition mechanism looks pretty straightforward, but what if the π-bond is asymmetrical? How can we tell which side the –X will add to?
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Lecture 183
General properties of hydrohalogenation
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General properties of hydrohalogenation
This is the most simple addition reaction, mostly because this is the example that we use to teach the mechanism in the first place. You should already be familiar with this reaction.
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Lecture 184
General properties of acid-catalyzed hydration
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General properties of acid-catalyzed hydration
This is the first of three ways to add alcohol to a double bond. Similar to hydrohalogenation in terms of mechanism, however it will require a protonation and deprotonation step since it is acid-catalyzed.
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Lecture 185
General properties of oxymercuration-reduction
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General properties of oxymercuration-reduction
This is the second of three ways to add alcohol to a double bond. It is similar in acid-catalyzed hydration in terms of products, but the mechanism is WAY different.
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Lecture 186
A worked example of the acid catalyzed oxymercuration reduction mechanism
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A worked example of the acid catalyzed oxymercuration reduction mechanism
Opening of 3-membered intermediates/molecules always results in anti-addition.
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Lecture 187
General properties of hydroboration oxidation
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General properties of hydroboration oxidation
This is the last of three ways to add alcohol to a double bond. This reaction creates alcohols that are much different from the first two methods, so pay attention to the differences!
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Lecture 188
Catalytic Hydrogenation: Mechanism
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Catalytic Hydrogenation: Mechanism
These reactions add hydrogen which reduces π-bonds to alkanes.
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Lecture 189
General properties of halogenation
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General properties of halogenation
One of the most popular addition reactions, this is the primary method for making vicinal dihalides.
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Lecture 190
General properties of halohydrin formation
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General properties of halohydrin formation
Indentical mechanism to halogention, except with water as the nucleophile in the second step. Why would water prefer to react as a nucleophile over a halogen anion? Let’s find out.
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Lecture 191
A worked example of the halohydrin mechanism
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A worked example of the halohydrin mechanism
Opening of 3-membered intermediates/molecules always results in anti-addition.
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Lecture 192
General properties of epoxidation
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General properties of epoxidation
This reaction adds a 3-membered cycle ether (epoxide functional group) to an alkene using reagents called peroxy acids. These epoxides are highly strained, so they can react in very useful ring-opening reactions, which we will discuss later.
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Lecture 193
The mechanism of how halohydrins make epoxides via intramolecular SN2
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The mechanism of how halohydrins make epoxides via intramolecular SN2
Peroxy acids are compounds with the general molecular formula RCO3H. The most common examples are MCPBA and MMPP. These are essentially the same molecule, just with different –R groups.
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Lecture 194
Acid Catalyzed Epoxide Ring Opening
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Acid Catalyzed Epoxide Ring Opening
Ethers are generally unreactive. However, epoxides (3-membered cyclic ethers) are highly strained, so they are able to react with nucleophiles in ways a typical ether could not. Let’s take a look.
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Lecture 195
Syn Vicinal Dihydroxylation
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Syn Vicinal Dihydroxylation
In this reaction, we learn how to use certain agents to add diols to a double bond. This is also known as the 1,2-syn diols reaction.
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Lecture 196
Ozonolysis
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Ozonolysis
Ozonolysis is a form of oxidative cleavage that breaks through alkenes and replaces them with carbonyls on both ends. Just imagine the ozone functioning like tiny atomic scissors, cutting each alkene right in half!
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Lecture 197
General properties of double addition reactions to alkynes
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General properties of double addition reactions to alkynes
Alkynes contain two π-bonds, so when they are exposed to electrophiles, they do exactly what you would expect them to do: they react TWICE with them.
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Lecture 198
Double hydrohalogenation of alkynes
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Double hydrohalogenation of alkynes
Keep in mind that for some of these reactions, vinyl carbocations will be created. While unstable, these cannot rearrange, so don’t worry about carbocation rearrangements when reacting with alkynes!
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Lecture 199
Double halogenation of alkynes
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Double halogenation of alkynes
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Lecture 200
Vinyl alcohols yield tautomers
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Vinyl alcohols yield tautomers
Vinyl alcohols (alcohols directly on a double bond) undergo a process called tautomerization. We will devote an entire chapter to this process next semester, so you aren’t expected to fully understand it yet.
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Lecture 201
Markovnikov addition of alcohols yields ketones
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Markovnikov addition of alcohols yields ketones
Both acid-catalyzed hydration and oxymercuration-reduction of any alkyne leads to formation of a ketone. These reactions both yield a Markovnikov vinyl alcohol, which then tautomerizes.
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Lecture 202
Heterolytic vs Homolytic Bond Cleavage
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Heterolytic vs Homolytic Bond Cleavage
Radical reactions require an initial first step to get going. We call this reagent the radical initiator.
Chemical bonds can be cleaved in two ways: Heterolytically (ionic cleavage) and homolytically (radical cleavage).
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Lecture 203
The radical stability trend
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The radical stability trend
Radicals are unstable intermediates. So we’re going to have to discuss some ways to stabilize them. Unlike carbocations, allylic and benzylic radicals are ALWAYS most stable.
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Lecture 204
The one reaction that alkanes will actually undergo
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The one reaction that alkanes will actually undergo
Alkanes are the backbone of organic molecules, yet they are almost completely unreactive. The only reaction alkanes undergo is radical halogenation, the gateway to the rest of organic synthesis.
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Lecture 205
Radical Chain Reaction Mechanism
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Radical Chain Reaction Mechanism
Alkanes will react with diatomic halogens in the presence of heat, light or any other radical initiator.
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Lecture 206
Using the Hammond Postulate to describe radical chlorination
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Using the Hammond Postulate to describe radical chlorination
Early transition states could care less what they look like, whereas late transition states have to be much more careful about the arrangements they take.
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Lecture 207
Radical selectivity: Lilo vs. Dutchess Kate
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Radical selectivity: Lilo vs. Dutchess Kate
Not all radicals are born equal! Some of them are going to make pretty smart decisions from an energy perspective, while others literally can’t even. Let’s turn to some famous role models for guidance on this topic.
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Lecture 208
Overview of Hydrohalogention
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Overview of Hydrohalogention
The presence of radicals in some familiar looking addition reactions can completely change the product. Remember our friendly addition reaction hydrohalogenation? Notice that you achieve Markovnikov alkyl halide in this reaction
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Lecture 209
General features of Radical Polymerization
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General features of Radical Polymerization
Polymers are used to form plastics and other synthetic materials. These radical reactions use alkenes to link millions of repeating units together through an almost never-ending propagation step.
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Lecture 210
The general mechanism of Allylic Halogenation
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The general mechanism of Allylic Halogenation
The presence of radicals in some familiar looking addition reactions can completely change the product. Remember our friendly addition reaction halogenation? Notice that you achieve a vicinal dihalide in this reaction.
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