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chore: temp image path fix, need a config for this
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rhighs committed Oct 25, 2024
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76 changes: 38 additions & 38 deletions docs/lectures/organic-chemistry/lesson-4_24-09-2024.md
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Expand Up @@ -30,7 +30,7 @@ Heteratoms and bonds are responsible for the reactivity on a particular molecule


<p align="center">
<img src="./assets/dimehyl-ether.png" />
<img src="../assets/dimehyl-ether.png" />
</p>

- Lone pairs make $\ce{O}$ a base and a nucleophile
Expand All @@ -39,7 +39,7 @@ Heteratoms and bonds are responsible for the reactivity on a particular molecule
- This creates electron-deficient sites (partial positive charge, $\delta^+$) on those carbons, making them electrophilic (prone to be attacked by nucleophiles).

<p align="center">
<img src="./assets/double-bond-easily-broken.png" />
<img src="../assets/double-bond-easily-broken.png" />
</p>

- The $\pi$ bond is easily broken.
Expand All @@ -62,7 +62,7 @@ Heteratoms and bonds are responsible for the reactivity on a particular molecule
### Parts of a functional group

<p align="center">
<img src="./assets/parts-of-a-functional-group.png" />
<img src="../assets/parts-of-a-functional-group.png" />
</p>

- **Ethane**
Expand Down Expand Up @@ -96,7 +96,7 @@ Ethane consists of **nonpolar $\ce{C-C}$ and weakly polar $\ce{C-H}$ bonds**, re
Hydrocarbons are compounds make up of only the elements carbon and hydrogen; they may be aliphatic or aromatic

<p align="center">
<img src="./assets/alkane-alkene-alkyne-aromatic-compunds.png" />
<img src="../assets/alkane-alkene-alkyne-aromatic-compunds.png" />
</p>

- Aliphatic hydrocarbons have three subgroups
Expand All @@ -112,13 +112,13 @@ Hydrocarbons are compounds make up of only the elements carbon and hydrogen; the
- The **phenyl group**

<p align="center">
<img src="./assets/phenyl-group.png" />
<img src="../assets/phenyl-group.png" />
</p>

### Functional groups with carbon heteroatom $\ce{C-Z}$ $\sigma$ bonds

<p align="center">
<img src="./assets/c-z-sigma-bond.png" width=400/>
<img src="../assets/c-z-sigma-bond.png" width=400/>
</p>

The structure on the right shows a 3D molecular model where carbon is bonded to the heteroatom $\ce{Z}$ with an arrow indicating the direction of the electron density being pulled toward the more electronegative atom $\ce{Z}$.
Expand All @@ -128,7 +128,7 @@ The structure on the right shows a 3D molecular model where carbon is bonded to
> **Halogens** are highly reactive elements from Group 17 of the periodic table, including fluorine $\ce{F}$, chlorine $\ce{Cl}$, bromine $\ce{Br}$, and iodine $\ce{I}$. When a halogen forms a bond with another element, particularly carbon, the resulting compound is called a **halide**. Halides (e.g., alkyl halides) have polar carbon-halogen bonds due to the high electronegativity of halogens, making them reactive in organic chemical reactions like substitution and elimination.
<p align="center">
<img src="./assets/types-of-c-z-bonds.png" />
<img src="../assets/types-of-c-z-bonds.png" />
</p>

### Functional groups with $\ce{C-O}$ group
Expand All @@ -137,15 +137,15 @@ The structure on the right shows a 3D molecular model where carbon is bonded to
- The polar $\ce{C=O}$ bond makes the carbonyl carbon an electrophile, while the lone pairs on $\ce{O}$ allow it to react as a nucleophile and base

<p align="center">
<img src="./assets/carbonyl-group.png" width="300"/>
<img src="../assets/carbonyl-group.png" width="300"/>
</p>

**NOTE**: the carbonyl group also contains a bond that is more easily broken than a $\ce{C-O}$ bond

#### Atoms classification

<p align="center">
<img src="./assets/classes-of-carbon-and-hydrogen.png" />
<img src="../assets/classes-of-carbon-and-hydrogen.png" />
</p>

| **1. Carbon atoms** | **2. Hydrogen atoms** | **3. Alcohols and alkyl halides** | **4. Amines and amides** |
Expand All @@ -154,11 +154,11 @@ The structure on the right shows a 3D molecular model where carbon is bonded to
| 6-acetylmorphine | 6-acetylmorphine | Cortisol | Motuporamine B |
| **Carbon atoms** are classified by the number of carbon atoms bonded to them; a 1° carbon is bonded to one other carbon, and so forth. | **Hydrogen atoms** are classified by the type of carbon to which they are bonded; a 1° hydrogen is bonded to a 1° carbon, and so forth. | **Alcohols and alkyl halides** are classified by the type of carbon to which they are bonded; a 1° alcohol has an OH group bonded to a 1° carbon, and so forth. | **Amines and amides** are classified by the number of carbon atoms bonded to the nitrogen atom; a 1° amine has one C–N bond, and so forth. |
<p align="center">
<img src="./assets/big-molecules-with-numbers.png" />
<img src="../assets/big-molecules-with-numbers.png" />
</p>

<p align="center">
<img src="./assets/classes-for-groups.png" />
<img src="../assets/classes-for-groups.png" />
</p>

#### Why all this fuss?
Expand Down Expand Up @@ -198,7 +198,7 @@ In an ionic compound, such as sodium chloride $\ce{NaCl}$, the positively charge
> Ion-ion interactions are among the strongest types of attractive forces in chemistry because they involve full charges and lead to the stable, rigid structures seen in many ionic solids. This is what gives ionic compounds distinct physical properties, like hardness and high thermal stability.
<p align="center">
<img src="./assets/electrostatic-na-cl.png" width=300 />
<img src="../assets/electrostatic-na-cl.png" width=300 />
</p>

This image describes **ion-ion interactions**, which are the strong electrostatic attractions that occur between oppositely charged ions in ionic compounds. These interactions are a type of **intermolecular force** but are much stronger than the forces found between covalent molecules.
Expand Down Expand Up @@ -231,15 +231,15 @@ The strength of van der Waals forces increases with the size and surface area of
- This can induce a temporary dipole in another molecule.

<p align="center">
<img src="./assets/van-der-waals-temp-dipole.png" />
<img src="../assets/van-der-waals-temp-dipole.png" />
</p>

#### var der Waals forces in relation with surface area

All compunds exhibit van der Waals forces $\rightarrow$ The larger the surface area of a molcules, the larger the attractive forces between two molecules, and the stronger the intermolecular forces.

<p align="center">
<img src="./assets/van-der-waals-forces-and-area.png" />
<img src="../assets/van-der-waals-forces-and-area.png" />
</p>

#### var der Waals forces and polarizability
Expand All @@ -258,7 +258,7 @@ Dipole-Dipole interactions are the attractive forces between the permanent dipol
**NOTE**: These attractive forces caused by permanent dipoles are much stronger than weak van der Waals forces

<p align="center">
<img src="./assets/acetone-dipole-dipole.png" />
<img src="../assets/acetone-dipole-dipole.png" />
</p>

#### Intermolecular non-covalent bonding forces
Expand All @@ -268,7 +268,7 @@ Dipole-dipole interactions can occur when both the drug and the binding site hav
This orientation is **beneficial** if it allows other functional groups on the drug to interact with the corresponding regions of the binding site effectively, enhancing the binding strength.

<p align="center">
<img src="./assets/dipole-binding-site.png" />
<img src="../assets/dipole-binding-site.png" />
</p>

However, if the dipoles align but the other binding groups on the drug are **not positioned correctly**, this orientation can be **detrimental**, reducing the effectiveness of the interaction.
Expand All @@ -281,7 +281,7 @@ The strength of dipole-dipole interactions decreases with distance between the d
#### Hydrogen bonding

<p align="center">
<img src="./assets/hydrogen-bonding.png" />
<img src="../assets/hydrogen-bonding.png" />
</p>

Hydrogen bonding typically occurs when a hydrogen atom bonded to O, N, or F, is electrostatically attracted to a lone pair of electrons on an O, N, or F atom in another molecule.
Expand All @@ -293,7 +293,7 @@ They vary in strength between $\text{5-25 kJ/mol}$ and are weaker than electrost
The electron deficient hydrogen is called a ***hydrogen bond donor*** $\rightarrow$ **HBD**. The electron rich heteroatom on the other hand is called a ***hydrogen bond acceptor*** $\rightarrow$ **HBA**.

<p align="center">
<img src="./assets/hbd-hba.png" />
<img src="../assets/hbd-hba.png" />
</p>

- $\ce{X-H}$ is a hydrogen bond donor (HBD), with the hydrogen being $\delta^+$.
Expand All @@ -306,7 +306,7 @@ In this mechanism, a drug molecule may contain such donor or acceptor groups to
In hydrogen bonds the inteaction involves orbitals and is **directional**, optimum orientation is where the $\ce{X-H}$ bond points directly to the lone pair on $\ce{Y}$ such that the angle between X, H and Y is $\ce{180°}$

<p align="center">
<img src="./assets/drug-orientation-to-target.png" />
<img src="../assets/drug-orientation-to-target.png" />
</p>

#### Typical H-Bond donors and Acceptors in eeceptor-proteins
Expand Down Expand Up @@ -341,7 +341,7 @@ where $\propto$ denotes inverse proportionality.
**NOTE**: Ionic bonds are the most important initial interactions as a drug enters the binding site

<p align="center">
<img src="./assets/ionic-interactions-drug.png" />
<img src="../assets/ionic-interactions-drug.png" />
</p>

Ionic bonds are the strongest non-covalent interactions, typically ranging from $\text{20-40 kJ/mol}$, because they involve full charges. This makes them much stronger than hydrogen bonds or van der Waals forces, which rely on partial or temporary charges. Unlike other interactions, the strength of ionic bonds decreases less rapidly with distance, meaning they remain effective over larger distances. Additionally, in hydrophobic environments where water can't interfere, ionic bonds become even stronger, playing a crucial role in stabilizing interactions in biological systems.
Expand Down Expand Up @@ -369,14 +369,14 @@ The boiling point of a compund is referred to as the temperature at which liquid
- A good example is water: it's high boiling point is due to its extensive hydrogen **bonding network**, which requires a significant amount of energy to break. This is why water boils at a much higher temperature than many other small molecules.

<p align="center">
<img src="./assets/increasing-boiling-point.png" />
<img src="../assets/increasing-boiling-point.png" />
</p>

- The relative strength of the intermolecular forces increases from pentane to butanal to 1-butanol.
- The boiling points of these compounds increase in the same order.

<p align="center">
<img src="./assets/pentane-butanal-butan-1-ol.png" />
<img src="../assets/pentane-butanal-butan-1-ol.png" />
</p>

**Other factors contributing to the boiling point value**
Expand All @@ -386,7 +386,7 @@ The boiling point of a compund is referred to as the temperature at which liquid
- For example, **pentan-3-one** has a larger surface area than **acetone**, which results in stronger intermolecular forces and a higher boiling point (102°C for pentan-3-one vs. 56°C for acetone).

<p align="center">
<img src="./assets/surface-area-polarizability-bp.png" />
<img src="../assets/surface-area-polarizability-bp.png" />
</p>

- **Polarizability**:
Expand Down Expand Up @@ -415,19 +415,19 @@ For covalent molecules of approximately the same molecular weight, the melting p
- The stronger the intermolecular attraction, the higher the melting points.

<p align="center">
<img src="./assets/melting-point-interactions-trend.png" />
<img src="../assets/melting-point-interactions-trend.png" />
</p>

<p align="center">
<img src="./assets/pentate-butanal-butan-1-ol-mp.png" />
<img src="../assets/pentate-butanal-butan-1-ol-mp.png" />
</p>

#### The effect of symmetry on melting pointso

- For compunds having the same functional group and similar molecular weights, **the more compact and symmetrical the shape, the higher the melting point**.

<p align="center">
<img src="./assets/symmetrical-neopentene-comparison.png" />
<img src="../assets/symmetrical-neopentene-comparison.png" />
</p>

- A compact symmetrical molecule like neopentane packs well into a crystalline lattice whereas isopentane does not. It has a much higher melting point than isopentane.
Expand All @@ -439,7 +439,7 @@ For covalent molecules of approximately the same molecular weight, the melting p
Solubility is defined as the extend to which a compound, called a solute, dissolves in a liquid, called a solvent. The energy needed to break up the interactions between the molecules or ions of the solute comes from new interactions between the solute and the solvent.

<p align="center">
<img src="./assets/solute-solvent-interactions.png" />
<img src="../assets/solute-solvent-interactions.png" />
</p>

#### Solubility trends
Expand All @@ -460,7 +460,7 @@ hexane).
Most ionic compounds are soluble in water, but insoluble in organic solvents. To dissolve an ionic compund, the strong ion-ion interactions must be replaced by many weaker ion-dipole interactions.

<p align="center">
<img src="./assets/ion-ion-weakening.png" width=400 />
<img src="../assets/ion-ion-weakening.png" width=400 />
</p>

> 💡 What is an ion-dipole interaction?
Expand All @@ -473,15 +473,15 @@ Most ionic compounds are soluble in water, but insoluble in organic solvents. To
An organic molecule is water soluble only if it contains one polar functional group capable of hydrogen bonding with the solvent for every five $\ce{C}$ atoms in contains. Compare the solubility of butane and acetone in $\ce{H2O}$ and $\ce{CCl4}$

<p align="center">
<img src="./assets/butane-acetone-solubility.png" width=400 />
<img src="../assets/butane-acetone-solubility.png" width=400 />
</p>

#### Butane and acetone solubility

Since butane and acetone are both organic compounds, they are both soluble in the organic solvent $\ce{CCl4}$. Butane, which is nonpolar, is insoluble in $\ce{H2O}$. Acetone is soluble in $\ce{H2O}$ because it contains only three $\ce{C}$ atoms and its $\ce{O}$ atom can hydrogen bond with an $\ce{H}$ atom of $\ce{H2O}$.

<p align="center">
<img src="./assets/butane-acetone-solubility-2.png" width=400 />
<img src="../assets/butane-acetone-solubility-2.png" width=400 />
</p>


Expand Down Expand Up @@ -517,7 +517,7 @@ There are several different B vitamins, so a subscript is added just to distingu
- Vitamin A is water insoluble because it contains only one OH group and 20 carbon atoms.

<p align="center">
<img src="./assets/bcarotene-vitamin-a.png" width=400 />
<img src="../assets/bcarotene-vitamin-a.png" width=400 />
</p>

#### Vitamin C
Expand All @@ -527,7 +527,7 @@ There are several different B vitamins, so a subscript is added just to distingu
- Each carbon atom is bonded to an oxygen which makes it capable of hydrogen bonding, and thus, water soluble.

<p align="center">
<img src="./assets/vitamin-c.png" width=200 />
<img src="../assets/vitamin-c.png" width=200 />
</p>

### Functional groups and electrophiles
Expand All @@ -538,7 +538,7 @@ There are several different B vitamins, so a subscript is added just to distingu
- An electronegative heteroatom like $\ce{N}$, $\ce{O}$, or $\ce{X}$ makes a carbon atom electrophilic, as shown below.

<p align="center">
<img src="./assets/electrophilic-example.png" width=400 />
<img src="../assets/electrophilic-example.png" width=400 />
</p>

- In the examples, a partially positive carbon atom ($\delta^+$) is attached to an electronegative atom (like $\ce{Cl} or $\ce{OH}$), making the carbon **electrophilic** (electron-poor), which is susceptible to attack by nucleophiles.
Expand All @@ -548,25 +548,25 @@ There are several different B vitamins, so a subscript is added just to distingu
A lone pair on a heteroatom makes it basic and nucleophilic

<p align="center">
<img src="./assets/some-base-nucleophiles.png" width=400 />
<img src="../assets/some-base-nucleophiles.png" width=400 />
</p>

$\pi$ bonds create nucleophilic sites and are more easily broken than $\sigma$ bonds.

<p align="center">
<img src="./assets/nucleophiles-with-pibonds.png" width=400 />
<img src="../assets/nucleophiles-with-pibonds.png" width=400 />
</p>

An electron-rich carbon reacts with an electrophile, symbolized as $\text{E}^+$. For example, alkenes contain an electron-rich double bond, and so they react with electrophiles $\text{E}^+$.

<p align="center">
<img src="./assets/pibond-nuclephile-reaction-electrophile.png" width=400 />
<img src="../assets/pibond-nuclephile-reaction-electrophile.png" width=400 />
</p>

Alkyl halides possess an electrophilic carbon atom, so they react with electron-rich nucleophiles.

<p align="center">
<img src="./assets/alkyle-halide-reaction-electro-nucleophile.png" width=400 />
<img src="../assets/alkyle-halide-reaction-electro-nucleophile.png" width=400 />
</p>

#### Biomolecules
Expand All @@ -584,5 +584,5 @@ Alkyl halides possess an electrophilic carbon atom, so they react with electron-
- **Lipids**: commonly form from fatty acids and alcohols

<p align="center">
<img src="./assets/example-biomolecules.png" width=400 />
<img src="../assets/example-biomolecules.png" width=400 />
</p>
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