Organic Chemistry

Agenda

Hydrocarbons
Alkanes, Alkenes, Alkynes, Alkyls
Hydroxyls
Alcohols, Ethers, and Phenols
Carbonyls
Aldehydes and Ketones
Carboxyls
Carboxylic Acids and Esters
Aminos
Amines and Amides

Learning Objectives

 Discuss organic/inorganic chemistry, bonding characteristics of the carbon atom,

hydrocarbons/hydrocarbon derivatives and molecular/structural formulas of alkanes.
 Recognize alkanes using the IUPAC rules.
 Describe unsaturated hydrocarbons, alkenes/alkynes characteristics and their molecular/structural
formulas.
 Identify alkenes/alkynes using IUPAC rules.
 Examine the bonding characteristics of the oxygen atom and the structural characteristics of
alcohols, phenols, and ethers.
 Distinguish alcohols, phenols and eithers using IUPAC rules.
 Describe the structural characteristics of compounds containing a carbonyl group.
 Identify aldehydes, ketones, carboxylic acids, and esters using IUPAC rules.
 Discuss the bonding characteristics of nitrogen and the structure/classification of amines/amides.
 Recognize amines and amides using the IUPAC rules.

Organic Compounds
Organic Chemistry: the branch of chemistry that deals with carbon-based covalent compounds.
 Contain C – C and C – H bonds.
o Examples: lipids, carbohydrates, proteins, nucleic acids, coal, petroleum, natural gas.
o Carbon monoxide and carbon dioxide molecules are not considered to be organic.

Organic compounds are incredibly common.

 96% of all known compounds are organic.
 More than nine million are known.

Organic Compounds Inorganic Compounds

 Covalently bonded.  Ionically bonded.
 Weak interparticle forces.  Strong interparticle forces.
 Often flammable.  Usually not flammable.
 Usually insoluble in water.  Usually soluble in water.
 Nonconductive.  Conductive.
 Usually slow rates of chemical reactions.  Usually fast rates of chemical reactions.

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 Organic Chemistry
While both organic and inorganic compounds are both vital to life there are many uses of organic
compounds in everyday life.
 Food
 Shelter
 Clothing
 Ski waxing
 Hormones

Hydrocarbons (Hydrogen + Carbon)

Organic compounds have a common structure known as hydrocarbon.
 Hydrocarbons: A chain made from carbon and hydrogen.
o Sometimes called the backbone or skeleton.

 Functional groups: additional groups that attach to the hydrocarbon and give it special physical and
chemical properties.

Hydrocarbon Functional Group

Hydrocarbons can form single double and triple bonds.

And they can form a variety of shapes and structures.

Types of Formulas
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 Organic Chemistry
Normal hydrocarbon chains are simple, straight chains.
Branched hydrocarbon chains have additional side-chains attached.

There are many ways to put branched chains together.

Isomers are chains with identical chemical formulas, but different structures.

Isomers

C2H6O C2H6O

Types of Hydrocarbons

Functional groups we will talk about in this course:

1. Alkane 3. Alkyne 5. Ether 7. Ketone 9. Ester 11. Amide

2. Alkene 4. Alcohol 6. Aldehyde 8. Carboxylic Acid 10. Amine

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 Organic Chemistry
Saturated hydrocarbons: Hydrocarbons with only single bonds. Alkanes.
Unsaturated hydrocarbons: Hydrocarbons with at least one double or triple bond. Alkenes, Alkynes.

Hydrogeneration reactions (addition reactions): Use hydrogen gas to saturate and remove double and
triple bonds.

Alkanes (single-bond hydrocarbon)

Has no functional groups. Is non-polar, odorless, colorless, and often used in skin softeners and as “gas”
fuel sources. Is less dense than water, insoluble in it, and has a lower melting and boiling point than
other organic compounds of comparable size.

Suffix: -ane

Hydrocarbons are used as fuel sources because of the combustion reactions they can initiate.
 Word equation: alkane + oxygen gas → carbon dioxide gas and water
 Formula equation: CnH2n+2 (g) + O2 (g) → CO2 (g) + H2O (l)

IUPAC Naming (3-steps)

1. Identify the main chain.
2. Functional group positions are stated with numerical prefixes that indicate the locations of carbons
that the functional groups are bonded to.
3. Functional group type and the suffix that denotes that group.

Example (IUPAC Naming)

3 carbons = “prop”
No functional groups, double or triple bonds, or branches = “-ane”
Name: propane

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 Organic Chemistry
Example (balance the equation for propane gas) Reactants Products
Equation: C H (g) + O (g) → CO (g) + H O (l) C: 3 C: 1 3
Balanced: C H (g) + 𝟓 O (g) → 𝟑 CO (g) + 𝟒 H O (l) H: 8 H: 2 8
O: 2 10 O: 3 7 10

Alkenes (double-bond hydrocarbon)

Has at least one double-bond. Is odorless, colorless, flammable, and has a low boiling and melting point,
and is insoluble in water (like alkanes). It is used in chemical feedstock. Small chains exist as gases while
larger chains as a waxy solid.

Suffix: -ene

Example (IUPAC Naming)

H3C CH2 CH CH CH 3
2
Count carbons from the shortest end (right to left, in this case).
Prefix with the carbon number, dash, then base name: 2-pent
Add the suffix, since this is an alkene, use -ene.
Name: 2-pentene.

Alkynes (triple-bond hydrocarbon)

Has at least one triple-bond. Like both alkanes and alkenes, odorless, colorless, flammable, low melting
and boiling points, and insoluble in water. Like alkenes, they are used as chemical feedstock, while small
chains exist as gases, and larger chains as a waxy solid.

Suffix: -yne

Example (IUPAC Naming)

HC C C C CH 3
1 3
Count carbons from the shortest end (Left to right, in this case).
Prefix with the number of the carbons: 1,3, hyphen, and the base name: 1,3-pent
Then add an “a” for grammatical clarity.
Add the Greek “di” to signify that there are two functional groups.
Finally, suffix with -yne since it is an alkyne.
Name: 1,3-pentadiyne.

Alkyls (side-chain hydrocarbon)

Are hydrocarbons with side groups of carbons. The properties are the same as alkenes and alkyne and
are suffixed with -yl.

Example (IUPAC Naming)

Two alkyls are fixed to carbon 2 so prefix with 2,2-.
Each is a single prefix with meth-.
2 Prefix with the Greek di- since there are two and suffix with -yl.
Finally add the main chain which is an alkane with 4 carbons.
Name: 2,2-methylbutane.

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 Organic Chemistry
Example (IUPAC Naming)
chain-start
2 alkyls are fixed to a 7-carbon chain.
end 4 The 7-carbon chain is a heptane.
The alkyls are placed in alphabetical order as prefixes.
7 3 meth-
A hyphen is placed between both prefixes but not before the main chain.
Name: 4-ethyl-3-methylheptane.

eth-
Aromatics (cyclical)
All we need to know is that they’re cyclical.

Hydroxyls
Has an OH covalently bonded to an organic compound.
 This is different then a hydroxide which is a polyatomic ion that forms ionic bonds.

There are three different types of hydroxyls:

 Alcohols
 Ethers
 Phenols
Alcohols (hydroxyl attached [OH] not hydroxide)
Have a hydroxyl functional group OH, higher boiling and melting points and range from soluble to
insoluble. They are used for alcoholic beverages and as chemical precursors (reactants).

In alcohols, the hydroxyl is attached to the end of the carbon chain creating a dipole. Longer chains have
weaker poles since carbon chains are non-polar.

Suffix: -ol

There are 3 different types of alcohols. It’s based on how man carbons (R) are bonded to the hydroxyl
carbon:

Uses:
Chemical Precursors for pharmaceutical applications.
Ethanol = the alcohol we drink
Menthol is extracted from mint and used as flavouring.
Steroids such as cholesterol are alcohols.

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 Organic Chemistry

Example (IUPAC Naming)

OH hydroxyl 3 chain carbon with a hydroxyl.
Uses the longer prefix for clarity: propan-
Prefix with the carbon position of the hydroxyl
H3C CH CH3 Name: 2-propanol.
2

Example (IUPAC Naming)

OH
2 chain carbon: ethan-
2 hydroxyls are represented on the first carbon by: 1,1
H3C CH Suffix with the Greek -di since there are two hydroxyls.
1 An “e” is added before the -di for pronunciation.
Name: 1,1-ethandiol.
OH

Ethers (oxygen separating 2 chains)

Ethers have an oxygen holding two carbon chains together.

Phenols (aromatic with a hydroxyl)

Are aromatics with a hydroxyl attached.

Carbonyls (O double-bonded)
Carbonyl is when there is a lone oxygen double-bonded to a carbon.

Aldehyde Ketone *Carboxylic Acid **Ester

*The carbonyl in Carboxylic Acid and Esters are part of a more complex “Carboxyl” group.
*Ester is an ether with a double-bonded lone oxygen.

Aldehyde (double-bonded O at the beginning)

Has the functional group (double-bonded oxygen) at the end (or beginning) of the chain.

Aldehydes have low melting and boiling points and range from soluble to insoluble. They are used as
chemical precursors, preservatives, disinfectants, and pesticides. Their polarity is between hydrocarbons
and hydroxyls.

Suffix: -al

Example (IUPAC Naming)

7 chain carbon, prefix with “heptan-“ O
Suffix with “-al” 7
Name: heptanal. H3C CH2 CH2 CH2 CH2 CH2 CH

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 Organic Chemistry

Ketone (double-bonded O in the middle)

Have the functional group (double-bonded oxygen) in the middle of the chain.

Are pleasant smelling, used as organic solvents (ex. nail polish remover) and food components. Since the
carbonyl is in the middle, it is often slightly less polar than aldehydes.

Suffix: -one

Example (IUPAC Naming)

5-carbons: pentan- ; suffix: -one
3 Carbon number: 3
Name: 3-pentanone.

Example (IUPAC Naming)

O O O 10 carbon chain, prefix with “decan-“
Carbonyls at 2,3,8- ; suffix with “-one”
8 3 2 “e” for clarity, and tri- prefixed to -one.
H3C CH2 C CH2 CH2 CH2 CH2 C C CH3
Name: 2,3,8-decanetrione.

Carboxylic Acids (carbonyl/hydroxyl)

Has a high boiling and melting point, as well is highly soluble in water. It used as an acid
and food ingredient. The functional group is terminal, but a carbonyl and hydroxyl
combination. “R” in the diagram is the rest of the carbon chain.

Since there are two polar functional groups in one, they are the most polar functional group so far.
Acetic acid and citric acid are examples of carboxylic acid and can be used as weak cleaners.

Suffix: -oic acid

Example (IUPAC Naming) O

4 carbon chain: butan-
H3C CH2 CH2 C
Carboxylic acid suffix: -oic acid
Name: butanoic acid. OH

Esters (carboxylic acid/ether)

Part carboxylic acid part ether. Used in fragrant, fruity
scents and perfumes.

Esterification is the chemical reaction that produces ester and water. It involves combining carboxylic
acid and alcohol.

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 Organic Chemistry
Aminos (nitrogen)
An amino is a nitrogen bonded to at least one organic compound.

There are two types of aminos:

 Amines
 Amides

Amines
The functional group is a nitrogen atom. There are 3 types. Primary (1°), Secondary (2°), Tertiary (3°).

Primary amine: a nitrogen that is bonded to one carbon.

Secondary amine: a nitrogen that is bonded to two carbons.
Tertiary amine: a nitrogen that is bonded to three carbons.

Amines are found in foods, but the most important ones are:
Neurotransmitters: chemicals that help relay information between cells in the nervous system.
Examples: epinephrine, dopamine, serotonin, acetylcholine.
Amino acids: used as the building blocks for making proteins.
Examples: cystine, methionine, glycine, lysine.

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 Organic Chemistry
Amides (carboxylic acid/amine)
Are a cross between an amine and carboxylic acid.
They are like esters but have a nitrogen present.

The amide functional group is very polar. They’re attracted to one another (like water), making them
hard to break up. They tend to be solid at room temperature.

The most well-known example of amides are polypeptide (protein) chains. When amino acids
polymerize, amides are created at the bonding site.

Amide!

Additional Notes (what to study/things to know)

Terminology (bolded and in blue).
Applications for specific compounds.

The most important concept in this unit is identifying and naming

organic compounds.
 Make sure you understand what is required of you.
Name: 3,4,4,8-tetraethyl-5-methyldec-2,6,7-trien-1,5,6-triol-9-ynal

Side-chains can exist on main chains for any functional group.

 While you will only be responsible for naming side chains on hydrocarbons,
understand that any main chain can have them.
Naming and describing carbon numbers for side-chains (alkyls) is something that
happens before you describe the main chain.
 This means alkyls go in the front of the name.
 Remember: a chain zigzagging is not branching. Branching is when there is
more than one chain that emerges.
 The main chain is always the longest carbon chain with a functional group.
o If no chain has a functional group, then the main chain is the longest
alkane.
 𝐂𝐇𝟑 − (𝐂𝐇𝟐 )𝟑 − 𝐂𝐇𝟑 = pentane (5-carbon chain alkane - shortform)

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