Unit B- Organic Chemistry

What is an Organic Compound? (3)

A molecular compound containing carbon with the exception of CO2, carbonates, carbides and cyanides
due to carbons 4 valence electrons, it makes it the backbone of many complex molecular compounds, often creating long chains and crystal structure
the ability to make long chains make carbon the building block of all life on earth, “carbon based lifeform”

Common uses of fossil fuels (hydrocarbons)

Coal, Oil, and Natural Gas

Alkane Definition

A saturated Hydrocarbon with any single covalent bonds between its carbon atoms

Hydrocarbon Deffinition:

An atom containing only carbon and hydrogen atoms

What is the general formula for alkanes?

CₙH₂ₙ₊₂

Cyclic Alkanes:

A hydrocarbon in which the main structure consists of a chain of carbon atoms joined to form a closed ring

Orientations of Alkanes

Straight Chain Alkane
Cyclic Alkane

Alkyl Groups (3)

An alkyl group is a type of substituent group
One or more carbon atoms that form a branch off the main chain of a hydrocarbon.
Alkyl groups are named with the prefix indicating the number of carbons atoms in the branch, like in your table, however you add a -yl suffix.

Substituent Group

an atom or group that replaces hydrogen in an organic molecule.

Structural Isomerism (2)

Most hydrocarbons with 4 or more carbon atoms exhibit structural isomerism.
Structural isomerism occurs when 2 molecules each have the same number and types of atoms but these atoms are bonded in different ways.

Naming Alkanes (1-20)

1 - methane
2 - ethane
3 - propane
4 - butane
5 - pentane
6 - hexane
7 - heptane
8 - ocatne
9 - nonane
10 - decane
11 - undecane
12 - dodecane
13 - tridecane
14 - tetradecane
15 - pentadecane
16 - hexadecane
17 - heptadecane
18 - octadecane
19 - nondecane
20 - Icosane

Uncommon Alkyl Groups + Alhpa priority

Isopropyl, butyl isobutyl, sec-butyl, tert-butyl
(ensure these are not apart of the longest carbon chain  
chose “i” for iso alpha priority 
for tert

iso means

same number

Alkyl Halides + How to name (4)

An alkane in which one or more hydrogen atoms have been
substituted with one or more halogen atoms.
Halides - implies halogen
Add the root of the halogen followed by o when naming

Does the di, tri, tetra change alpha priority?

No you ignore it, ex if u have dimethyl and ethyl, ethyl still comes first

Unsaturated Hydrocarbon:

An unsaturated hydrocarbon is an organic compound, consisting of a carbon and hydrogen, with one more double or triple bonds joining pairs of carbon atoms within the molecules.

Alkene (2)

a hydrocarbon with at least one carbon-carbon double bond
CnH2n

Alkyne (3)

a hydrocarbon that contains at least one carbon-carbon triple bond
CnH2n-2
Alkynes are linear

Naming Alkenes (3)

you have to include alkenes in your parent chain, even if it is not the longest possible change
Alkenes follow the same naming scheme as alkanes, except their ending is changed to “ene” instead of “ane”.
Methene isn’t included as we need a minimum of 2 carbons

Pi bond:

Double bond

2,3,4 pi bond:

di, tri, tetra

Stereoisomers

Molecules that have the same chemical formula and structural backbone, but with a different arrangement of atoms in space

Cis isomer

A stereoisomer in which the groups of interest are located on the same side of a double bond

Trans isomer

a stereoisomer in which groups of interest are located on opposite sides of a double bond

Limitations of Cis Trans

The cis and trans naming system is limited to simple molecules containing only 1 cis/trans group

When and when not to include the a in: Pent-3-ene or penta-3-ene etc

Standard: no a pent-3-ene
When you have diene triene etc
Penta-3-diene or penta-3-triene

Why are Alkynes are linear + cis

trans isomers

Functional Group

A group of atoms within a molecules that determines the properties of the molecule

Addition Reaction + three types

two molecules react to form one, hydrogenation, halogenation Hydrohalogenation

Hydrohalogenation

Alkene + Hydrogen Halide → Alkane with Alkyl halide subgroups

hydrogenation

hydrogen reacts with alkenes and alkynes to form a new compound.
In short hydrogens are added to either side of bond molecule goes from unsaturated (not enough h) to saturated (lots of h)
Alkene

Halogenation

A halogen such as bromine or chlorine reactions with an organic compound to form an Alkyl halide
creates an Alkane with Alkyl Halides
Alkene + Halogen → Alkanes with Alkyl Halide subgroup

Aromatic Hydrocarbons

• An unsaturated cyclic hydrocarbon with a pattern of bonding that makes it chemically stable.

• The most common aromatic is Benzene. (C6 H6 ) which is indicated by a hexagon with a circle All six bonds are equal in length.

Naming Benzenes

When Benzene is the parent chain we say “benzene on the end of the compound
When benzene is a substituent, it exists as a phenyl group as it is missing one hydrogen.

Phenyl group

a benzene ring (minus 1 hydrogen) that behaves as a substituent

Rules about ties with Cyclics

When there’s a tie with a cycloalkane/ene or a benzene. Generally we give priority to the cyclic but both are considered to be ok and will be marked correctly.

Alkenes or Alkynes will always take priority if they exists in the chain

Properties of Aromatic Hydrocarbons

Many aromatics are liquids at room temperature.
Their symmetrical structure causes them to be non-polar so they are insoluble in water.

Reactions with Aromatic Hydrocarbons

Normally unsaturated hydrocarbons (Alkenes/ynes) react very easily, however aromatics generally don’t like to bond easily due to their structure.

They generally undergo substitution reactions

Alcohol

Organic compound that contains the hydroxyl (-OH) functional group
Alcohols are generally considered to be Polar

What Functional group do Alcohols have?

hydroxyl (-OH) functional group

There are 3 types of Alcohols

Primary Alcohol: An alcohol in which the hydroxyl group is bonded to a terminal carbon atom
Secondary Alcohol: An alcohol in which the hydroxyl group is
bonded to a carbon atom with two alkyl groups bonded to it
Tertiary alcohol: An alcohol in which the hydroxyl group is bonded to a carbon atom with three alkyl groups bonded to i

Naming Alcohols

hydroxyl (-OH) functional group = Alkane name + ol,
Side chain: hydroxy

Reactions involving alcohols

Addition reactions with Alkenes and water form alcohol
Alcohols can be dehydrated to form alkenes and water
Combining two alcohols together can result in an ether (condensation reaction)

Hydration

Addition of H₂O (H and OH) across a double bond to form an alcohol

Alkenes vs Alkynes

when there’s a tie the Alkene takes numbering priority

Dehydration

Alcohol + Alcohol → Alkane with Ether subgroup + water

Markovnikov’s Rule

When a hydrogen halide or water molecule reacts with Alkenes, the hydrogen atom generally bonds to the carbon atom with the double bond that already has more hydrogen atoms bonded to it.
“Rich get richer” - The hydrogen likes to attach to the carbon with more hydrogen atoms

Ether

an organic compound containing an oxygen atom between 2 carbon atoms in a chain

Naming Ethers

when name ethers you see an oxygen bonded to differe carbon chains, the shorter carbon chain takes the (alkane name prefix) oxy, as it acts apart of the functional group and the longer carbon chain is left in its alkane form

Reactions involving ethers

Combining two alcohols together can result in an ether in a condensation reaction
Condensation reaction: A chemical reaction in which two molecules combine to form a larger molecule and water

Thiol

an organic compound that contains the sulfhydryl (-SH) group.
We will not name these - know the definition.
For your own knowledge thiols generally have a strong odor and are present in skunk spray and garli

What takes priority Alkenes Vs. Alcohols

Alcohol

Carbonyl Group

Carbon atom- double bonded to an oxygen atom, typically found in aldehydes and ketones
This group is responsible for the properties of ketones and aldehydes

Aldehyde

An organic molecule containing a carbonyl group that is bonded to at least 1 hydrogen atom.
on longer chains this is typically at the end

Ketone

An organic compound that contains carbonyl group bonded to two carbon atoms

Naming Aldehydes

Alkane prefix + al

Naming Ketones

Alkane prefix + one (don’t forget to number)

Properties of Aldehydes and Ketones

Due to the electronegativity of the oxygen atom, aldehydes and ketones are generally polar.
They are generally soluble in water due to this polarity.
Solubility decreases as the molecules get larger. The same goes for alcohols with long chains

Formations of Aldehydes and Ketones

Aldehydes and ketones are synthesized by the controlled oxidation of primary and secondary alcohols.
Primary Alcohol → aldehydes + water + oxygen
Secondary Alcohol + oxygen → ketones + water
Tertiary Alcohols do not oxidize
When we hydrogenate and Aldehyde or ketone, the double bond is broken and the product is an Alcohol
Ketone + water → Secondary Alcohol
 aldehydes + water → Primary Alcohol

Carboxylic acid

a weak organic acid containing at least one carboxyl group
When carboxylic acids are dissolved in water, they easily give up a hydrogen ion making them acidic.
These compounds are present in many sour foods such as citrus fruits giving them their distinct flavour.
A common mistake is to think that carboxylic acids are actually bases because of their OH group.
However due to the electronegativity differences we actually see the hydrogen dissociate in water very readily making it acidic.

Carboxyl group

a carbon atom that is double-bonded to 1 oxygen atom and single-bonded to hydroxyl group

Naming Carboxylic Acids

With Alkanes, you simply just swap the “e” on the end with an “oic” and add “acid”
When there are multiple carboxylic acids we use the phrase - (di, tri, tetra)carboxylic acid
exception: benzene is not benzenoic, its benzoic acid

Properties of Carboxylic Acids (5)

• oxygen and hydroxide make carboxylic acids very polar

• soluble in water and other polar molecules like alcohols.

• side chain increase solubility/plarity decreases

• Mp much higher than alkanes due to polarity

• The more carboxyl groups the more we see this difference

• because carboxylic acids readily dissociate hydrogen ions, we can see them react with bases to form ionic compounds and water in neutralization reaction

Esters

an organic compound that contains a carbonyl group bonded to a second oxygen atom which is bonded to another carbon atom
Esters are responsible for the odours found in fruits, plants, perfumes, synthetic flavours, and other cosmetics
Esters are formed by the condensation reaction of carboxylic acid and alcohol

Naming Esters

To name the ester, we must determine which part of the molecule was contributed by the alcohol. This is the part that does not include the carbonyl group. This give Ester’s the first part of their name.
The second part of the name comes from the carboxylic acid. “Oic acid” is dropped for “oate

Properties of Esters

An ester is similar to a carboxylic acid but it lacks a hydroxyl group. This make them less polar that carboxylic acids. They are most similar to aldehydes and ketones.
Small molecules are soluble in water
Slightly higher boiling points than alkanes
Small molecules are polar
Small molecules are gases, larger ones are waxy solids

Forming Carboxylic Acids

This is two step oxidation reaction

1. Alcohol + Oxygen (oxidizer) → Aldehyde + H2O
2. Aldehyde + Oxygen (oxidizer) → Carboxylic Acid

Forming Esters: Esterification

Carboxylic Acid + Alcohol → Ester + Water

Hydrolysis

Ester + Base → Carboxylic Acid + Alcohol

Amine

An organic compound, related to ammonia, that contains a nitrogen atom bonded to one or more alkyl groups on each molecule.
Amines generally have strong unpleasant odours associated with a “fishy” smell or decaying

Naming Amines

Note: Nitrogen likes to only make 3 bonds and would have a lone pair attached. This lone pair can be left out in these drawing
primary animes: in alkanes, drop the “e” for “amine” on the end of the parent chain
Secondary/Tertiary:

- Do not count longest chain through a nitrogen

- Begin with the longest chain that has nitrogen attached.

- Use N at the beginning of name like we use a number to

indicate alkyl groups to indicate substituent locations

- Add amine to the end of the nam

Types of Amines

There are three types of amines that are determined similarly to alcohols

Properties of Amines

• Nitrogen’s electronegativity make amines polar

• Small amines are polar making them: Have higher melting/boiling points than alkanes

• Decreasing boiling points from primary → tertiary

Amides

an organic compound that contains a carbonyl bonded to a nitrogen atom

Naming Amides

Amines are made from carboxylic acids and amines
Naming amides is similar to esters as there are two parts to the name.
First part: from the amine
Second part: from the acids

ie n - propyl butanamide

Properties of Amides

They are somewhat soluble in water, solubility decreases with chain length
Primary have higher melting

Polymers

A large, usually chain-like molecule that is built from small molecules.
Natural polymers exist in living organisms
Synthetic polymers are manufactured in materials such as plastics, rubbers, and textile

Monomer

One of the repeating small molecules that make up polymers

Polymerization, how to name polymer, two types of polymers

• reactions bring these monomer molecules together.

• Note the name for a polymer is derived from the monomer base, not what the chain would be called as an alkane in this case.

• In the polymerization of propene monomers we create polypropylene

• Both polyethylene and polypropylene are made from a single type of monomer. This makes them homopolymers

• Polymers made from two or more different types of monomers are called copolymers

Synthesizing Polymers

All the examples shown thus far are also considered addition polymers as they are the result of addition reactions

addition polymer example

• Teflon used in non stick coatings on cookware. (PTFE)

• polytetrafluroethene

• Teflons strong Carbon fluorine bonds make it inert and non flammable which is ideal for cooking

Plastic

• A synthetic polymer that can be molded under heat and pressure that then retains it’s shape

  • Typically derived from petrochemicals

• Plastics are held together by carbon carbon bonds and van der waals forces.

  • Chemically unreactive

aspirin

Today I will be discussing the organic compound acetylsalicylic acid, more commonly known as aspirin, which is one of the most widely used pharmaceutical drugs in the world. It is an organic compound containing carbon and functional groups, specifically an ester formed from salicylic acid and acetic anhydride.

Aspirin is both beneficial and potentially harmful to society. One major benefit is that it acts as a pain reliever by blocking COX enzymes, which are responsible for producing prostaglandins—chemicals that cause pain, inflammation, and fever.

Another important use is its ability to prevent blood clots. Aspirin reduces how sticky platelets are, lowering the risk of clots that can lead to heart attacks and strokes.

However, aspirin also has risks. Because it reduces blood clotting, it can increase the risk of internal bleeding, especially in the stomach. Long-term use may lead to ulcers, and it can be dangerous for children and teenagers due to Reye’s syndrome, which affects the liver and brain.

There are also environmental impacts. The production and improper disposal of pharmaceutical drugs like aspirin (like flushing it down the toilet)  can introduce chemicals into waterways, which may harm aquatic life.

In my opinion, while aspirin carries some significant risks, it is still essential for a functioning society, as long as individuals use it responsibly. People should follow proper dosage instructions (75-100 mg), consult doctors with any questions, and dispose of unused medication properly to minimize environmental harm (return unused medication to a pharmacy instead of flushing it) . Ultimately, in my opinion, when taken correctly, aspirin offers benefits that outweigh its risks for most people.

priority list for functional groups

Carboxylic Acids

Esters

Amides

Aldehydes

Ketones

Alcohol

Amine

Alkenes*/Alkynes

Ethers

Alkyl/ Alkyl Halides

does c count in alpha order, wb,iso, sec, tert, di, tri

yes then nos