Unit 2 Cheat Sheet

Hydrocarbons:
Representing Organic Structures: The different ways scientists represent organic structures
are:
● complete structural formulas (also referred to as complete formulas or structural
formulas)
● condensed structural formulas (also referred to as condensed formulas)
● line diagrams (also referred to as skeletal formulas)

Complete Structural Formulas:

● The complete structural formula of an organic compound shows all of the atoms involved
in the compound, represented by their atomic symbols, with bonds between atoms
represented by dashed lines.
● A single dashed line represents a single bond
● A double dashed line represents a double bond
● A triple dashed line represents a triple bond.

Condensed Structural Formulas:

● The dashes representing bonds are not included.

● Similar atoms bound to a carbon are grouped together and their
number is represented using subscripts.
● Units that are identical and repeat can be put within brackets and
subscripts are used to indicate how many times they repeat.
Units that branch off the main chain are also sometimes put in
brackets (CH3 CH2 CH3 —--------------->)

Line Diagrams:

● In line diagrams, carbon and hydrogen atoms are represented by lines, while all other
atoms are represented by their atomic symbol.
● Carbon atoms are represented at the ends of lines and at
the intersection of lines
● The presence of hydrogen atoms is implied by the
maximum amount of hydrogen atoms that could be bound
to a given carbon atom (remember carbon atoms can
have a maximum of 4 bonds).
● Double bonds are represented by double lines while triple
bonds are represented by triple lines. (C4H10 —------------------------>)
Alkanes: Some examples – namely methane, propane, butane and hexane – are organic
compounds that are classified as alkanes. All alkanes share similar structural properties:

● The carbon atoms have single bonds to other carbon atoms.

● They have a general formula of

Chemists use the name of compounds to describe them.

Naming the Structure:

1. The Number of Carbons in a Chain:

● RULE: The rule for determining the number of carbons in a chain is to count the longest,
uninterrupted chain of carbons.

With this in mind, we can count the longest, uninterrupted

continuous chain of carbons in our compound in two different
ways.

2. Identify where the subsequent group is:

● RULE: Number the carbon chain so that the substituent groups
get the lowest possible number. Where there are multiple
substituent groups, you number so that the overall combination
is as low as possible.
● When you have something branching off from the
main chain, it is called a substituent group.
● In this case, it is a single carbon chain.Using our knowledge from before, to
identify it as a single carbon, we will use the prefix “meth-”.
● To indicate that it’s a substituent group, it will end in “-yl”. Therefore this is a
methyl group.

3. So we have a methyl group attached to carbon 2 of a pentane molecule. We name

this compound, therefore: 2-methylpentane.

Method 1.
 Method 2.

Using this rule, we say that the methyl group is on carbon 2.

4. So we have a methyl group attached to carbon 2 of a pentane molecule. We name

this compound, therefore: 2-methylpentane

Note that it is very important to use:

● the proper numbering for the main carbon chain

● dashes between a number and a name
● commas between two or more numbers
Structural Isomers: Structural isomers are compounds that have the same molecular formula
(in this case C6H14 ) but different physical arrangements of atoms.

Other Substituent Groups: Organic compounds often contain substituent groups that aren't
hydrocarbons. To name these compounds we use prefixes to identify the different substituent
groups.

Alkenes, Alkynes and Aromatics

Factors that determine if a Hydrocarbon is saturated or unsaturated:

● Number of Hydrogens attached to a carbon

● Type of bond
Saturated Hydrocarbons: A saturated hydrocarbon has only single bonds to any atom and
therefore the maximum number of hydrogens attached possible.

Unsaturated Hydrocarbons: An unsaturated hydrocarbon has one or more double or triple

bonds between carbon atoms or is cyclic in nature, reducing the number of hydrogen atoms
attached.

Lipids: a hallmark of lipids is that:

● They tend to be made up of mostly hydrocarbons.

● They are generally insoluble in water.

Fats, oils, waxes, steroids and phospholipids are just several

subtypes of the broader lipid macromolecule group.

● Triacylglycerols or triglycerides, consist of a glycerol

backbone and a fatty acid tail.
● The glycerol is a small organic molecule with three
hydroxyl (-OH) groups
● The fatty acid tails consist of a large hydrocarbon chain
attached to a functional group known as a carboxyl.

Fatty acids: Both saturated and unsaturated fatty acids are made up predominantly of carbon and
hydrogen and have a glycerol group.

● Saturated fatty acids contain only single bonds, having the maximum number of
hydrogen atoms possible bonded to the carbon skeleton
● Unsaturated fatty acids contain one or more double bonds. In some cases, this double
bond can cause a kink in the fatty acid tail, which has significant implications for the
behavior of these molecules.
Alkenes: Are hydrocarbons that have at least one double bond in them. The general format for

an alkene with only one double bond is

Naming Alkenes: Naming alkenes follows the same rules as when you are naming alkanes:

● How many carbons are on the longest chain?

● Where is/are the double bond(s) located?
● If there are any substituents, what are they and where are they located?
● Assemble the name.
Structural Isomers - Alkenes: Recall from a previous learning activity that a structural isomer
is one where you have the same number of atoms but they are connected to each other
differently. We can also have structural isomers of alkenes, simply by moving around the double
bond, or other atoms within the molecule.

Geometric Isomers - Alkenes: In a geometric isomer, the atoms are attached in identical ways,
however the geometrical orientation of the atoms relative to each other changes.

● This occurs because in an alkene, the double bond prevents the atoms from being able
to rotate.
● As a result, the relative position of atoms on either side of the double bond is static,
whereas in an alkane, the relative position of atoms is constantly changing because of
the rotation about the bond.

Naming Geometric Isomers: it’s E/Z!

In order to delineate the different geometric isomers, we need a new set of rules to apply.You
will need to reference the periodic table for these problems.

1. What is the priority of atoms attached to carbons in the double bond: Start by
identifying the atoms that are attached to the carbons involved in the double bond.
Assign those atoms a priority based on their atomic number. The atom with the larger
atomic number gets the priority.
2. What is the Location of the high priority atoms: Once you’ve identified the priority on
each side, we then compare where the two high-priority atoms are located relative to
each other. When they are across from each other (i.e. on opposite sides of the double
bond), we use the letter “E” to indicate this. When they are beside each other (i.e. on the
same side as the double bond), we use the letter “Z” to indicate this.
3. Assemble the name
Alkynes: are hydrocarbons which have a triple bond between two or more carbons. The ending
for an alkyne is -yne.

● Just like alkenes, you need to ensure that the triple bond has the priority when
numbering the longest chain
● If a molecule contains both a double and a triple bond, the carbon chain is numbered so
that the first multiple bond gets the lower number.
● When examining an alkyne that is drawn as a line diagram, be careful when counting the
carbons. Remember, wherever a line ends, there is a carbon represented there.

Aromatics: Are unsaturated hydrocarbons with a ring structure and a bonding arrangement that
causes them to be chemically stable.

● Compound contains three alternating double bonds in a cyclohexane ring

● The family of organic compounds which are derivatives of benzene.

Benzene: This hydrocarbon is composed of six hydrogen and six carbon atoms
connected in a ring with three carbon-carbon double bonds. It is the simplest
aromatic hydrocarbon

● All the carbon-carbon bonds in benzene are the same length, which
indicates that the bonds are not in fact true double and single bonds.
● Typically, double bonds are shorter in length than single bonds.
 ● In benzene, the electrons that make up the double bonds are delocalized, or shared,
around all six carbon atoms.
● The arrangement of the electrons is indicated by placing a circle in the center of the
6-carbon ring. This arrangement of electrons also makes benzene particularly stable!

Naming Aromatics:

1. If benzene is the parent chain, name the side

chain using the same rules discussed previously
and the root “-benzene”. For compounds with two
substituent groups attached, the following prefixes
may be used instead of numbers: 1,2 = ortho-, 1,3 =
meta- and 1,4 = para-.

2. If the carbon chain is six or more carbon atoms

long, benzene is the side chain and is named
“phenyl-”.

Hydrocarbon Reactions:

Types: There are 3 main categories of organic reactions

● Combustion reactions
● Addition reactions
● Substitution reactions
Combustion: All hydrocarbons are capable of reaction with oxygen to form carbon dioxide and
water.
● In general, the smaller the parent chain, the more flammable the hydrocarbon
● The larger the parent chain, the less flammable the hydrocarbon
However, different hydrocarbons are capable of reacting differently
Alkane Reactions: The single, covalent bonds in alkanes makes them very strong as also fairly
unreactive.
● They can undergo substitution reactions, where halogen atoms replace hydrogen atoms.
● This is normally done in the presence of ultraviolet light.
● The product formed is an alkyl halide.
● Substitution Reaction (with a halogen)
Reactions of Alkenes + Alkynes: Because alkenes and alkynes are unsaturated, their most
important reactions are addition reactions.
● In addition reactions, atoms are added to the molecule, but no hydrogen atoms are lost.
● Additional reactions can occur with halogens, hydrogen, hydrogen halides and water.

Aromatic Reactions: Aromatic hydrocarbons undergo substitution reactions like alkanes, and
not addition reactions as alkenes do.
● The reactivity of aromatic hydrocarbons is intermediate between that of alkanes and
alkenes.
● The benzene structure is very stable, and its double bonds do not behave as double
bonds in alkenes, rather, as single bonds.
Markinov’s Rule: Used for predicting the products of hydrohalogenation and hydration
reactions (below)
● The hydrogen atom is added to the double bonded carbon with the most hydrogen
atoms attached.

Alcohols and Ethers:

Functional Groups: A functional group refers to an atom or a group of atoms within a molecule
that demonstrates consistent chemical properties, regardless of the compound in which it
appears.
Molecules containing similar functional groups often undergo similar reactions. Even when the
remaining portions of a molecule differ significantly, specific functional groups generally exhibit
predictable reaction patterns.

Alcohols: An alcohol is any compound with an -OH group (alcohol group) attached to single
bonded hydrocarbons (alkanes).
● Functional Group: R-OH (hydroxyl group).
Types of Alcohols: 1°, 2°, and 3° Alcohols. Alcohols can be further classified depending where
the hydroxyl is attached.
● Primary: hydroxyl is attached to a C that attached to only one other C
● Secondary: hydroxyl is attached to a C that is attached to two other Cs
● Tetrirary: hydroxyl is attached to a C that is attached to three other Cs
Naming Alcohols: The parent chain of the alcohol must be the longest that includes the carbon
holding the OH group.
● Give the -OH group the lower location number on the chain regardless of where alkyl
substituents occur, and replace the ending of the parent chain with an –ol.
Polyalcohols: Alcohols containing more than one hydroxyl group are also called polyalcohols.
Polyalcohols are named similarly to alcohols, with the exception of the prefix di-, tri-, etc before
the -ol ending.
● Hydroxyl groups can also be considered branches on a parent hydrocarbon chain. For
example, 1,2,3-propanetriol can also be called 1,2,3-trihydroxypropane.
Cyclic Alcohols: When naming aromatic or cyclic alcohols, the hydroxyl group is a group
attached to the parent ring, and the compounds are named as hydroxybenzenes.

Ethers: An ether is an organic compound that has two alkyl groups attached to an oxygen atom.
The alkyl groups may be the same or different.
● Functional group: R-O-R or R’-O-R”
● Ethers cannot form hydrogen bonds to themselves, like alcohols, but the V-shape make
ether molecules more polar than hydrocarbons.
● Ethers make good solvents because they have the ability to mix with both polar and
nonpolar substances, but are very unreactive because of the strong C-O bond.
Naming Ethers: Two ways to name ethers:
1) Add oxy to the smaller hydrocarbon, join it to the name of the larger alkane eg.
methoxyethane
2) List the two alkyl groups, followed by the word ether eg. methyl ethyl ether

Aldehydes and Ketones

Aldehydes:
● Smaller aldehydes have strong, unpleasant odours
● Larger aldehydes have pleasant, flowery odours
● Carbonyl group ALWAYS occurs at the end of a carbon chain
● Name: Take parent alkane name, drop –e, add suffix -al

Ketones:
● Organic compound used by animals and insects, called pheromones
● Carbonyl group occurs in the interior of the carbon chain
● Name: Take parent name, drop –e, add suffix –one.

Properties of Aldehydes/Ketones:
● Lower boiling points than analogous alcohols
● Less soluble in water than alcohols (no hydrogen bonding)
● More soluble in water than hydrocarbons
● Can mix with both polar and nonpolar substances, therefore are good solvents
Preparing Aldehydes/Ketones:
● Oxidation- implies a gain of oxygen or a loss of hydrogen
● Prepared using controlled oxidation of alcohols
● When a primary alcohol is oxidized → aldehyde
● When a secondary alcohol is oxidized → ketone
● Tertiary alcohol do not undergo oxidation as no H atom is available

Aldehydes and Ketones to Alcohol:

● Carbonyl group can undergo addition reaction with hydrogen
● Catalyst, high temperatures and high pressures are needed
● H atoms are added to carbonyl group, alcohol results
● Aldehydes produce 1° alcohols, ketones produce 2°

Carboxylic Acid Esters

Definition:
● Weak acids (e.g. vinegar, lactic acid)
● Found in citrus fruits, crab apples, rhubarb
● Also have distinctive odours
● Functional group🡪 ‐COOH (carboxyl group)
● Combines –OH (hydroxy) and –C=O (carbonyl)
Naming Carboxylic Acids:
● Take name of longest alkane or alkene parent chain
● Drop –e and add –oic, followed by the word acid
● If acids have multiple carboxyl groups, add the suffix –dioic acid
● Carboxyl groups can also be side groups on a molecule
★ You would name the parent chain, then note where the carboxyl groups are
located and write “carboxylic acid” with a prefix indicating how many carboxyl
groups are present
★ e.g. propane-1,2,3-tricarboxylic acid
★ Note: in these cases, the C atom in the carboxyl group does not count as
being part of the parent chain

Properties of Carboxylic Acids:

● Polar molecules that can form hydrogen bonds with each other and water
● Smaller members (1–4 C) are soluble in water
● Larger members are relatively insoluble
● Melting points are higher than analogous hydrocarbons due to increased intermolecular
attractions of polar carboxyl functional group
● Litmus test used to distinguish from other hydrocarbons
● They react with organic bases (via neutralization) to form organic “salts”
Esterification:
● When a carboxylic acid neutralizes an alcohol (base), the result is an organic “salt” (an
ester)
● This condensation / dehydration reaction is known as esterification
● Carboxylic acids react with an alcohol, forming an ester and water
● Acid catalyst and heat are required

Naming Esters:
● Functional Group: –COOR
● Name has two parts
● 1st part- name of alcohol
● 2nd part- acid. Change ending from -oic acid to -oate
Properties of Esters:
● The functional group of an ester is an alkylated carboxyl group (−COOR)
● With the loss of the polar −OH group, esters are less polar, less soluble in water, and
have lower melting and boiling points than their parent acids
● The acidity of the carboxylic acids is due to the H atom on their −OH group, and so
esters, having no −OH groups, are not acidic
Drawing Esters:
● When drawn, the carboxylic acid portion is written first then the alcohol even though it
comes second in the name
★ e.g. CH3CH2CH2COOCH3 = methylbutanoate

Hydrolysis:
● Esters undergo hydrolysis reactions in the presence of an acid or base
● Hydrolysis is a reaction in which a bond is broken by the addition of the components of
water, which forms two or more products
● This is the reverse of esterification and results in an acid and an alcohol
Fats/Oils
● Fats and oils are large ester molecules known as lipids
● There are two parts to a lipid: the alcohol component (glycerol) and the
long-chain carboxylic acid component (fatty acid)
● Since glycerol can form three ester bonds, the lipid formed is also known
as a triglyceride
● Generally, a lipid is called a fat if it’s solid at room temperature and an oil if
liquid at room temperature
Saponification:
● When a base is used to break a lipid into its parts (glycerol and fatty acid)
using an hydrolysis reaction, this is known as saponification
● The resulting sodium salt is commonly called soap

Amines and Amides:

Amines:

● Found in decomposing protein- give unpleasant odour

● Amines can be thought of as ammonia NH3, which hydrogen groups substituted as alkyl
groups
● Can be classified as primary, secondary or tertiary amines

Naming Amines:

● Primary amines can be named in two ways:

1. As a nitrogen derivative of an alkane, eg.
aminomethane
2. As an alkyl derivative of ammonia, eg.
methylamine
● Note: The IUPAC names for 2° and 3° amines include the
N- prefix to denote the substituted groups on the N atom of the amino group.

Properties of Amines:

● Higher boiling and melting points than hydrocarbons of similar size

● Smaller amines are readily soluble in water
● Amines boil at lower temperature than do alcohols of similar size
Preparing Amines:

Amides:

● Carbonyl group directly attached to an N atom

● Amides form the backbone of all protein molecules
● Functional Group (Below)

Naming Amides:

● Naming is similar to esters- Considered in two parts

● Part 1- derived from amine
● Part 2- derived from acid (separated into two words)
● When one or more alkyl groups are attached to the N atom in the amide linkage, the
italicized uppercase letter N is used to clarify the location of the group.
Properties of Amides:

● Weak bases, generally insoluble in water

● Lower-weight amides slight soluble in water
● Amides whose N are bonded to two H have high melting/boiling points than amides with
more R groups

Preparing Amides:

● Carboxylic acids react with ammonia or with a 1° or 2° amines to produce amides (type
of organic salt)
● Carbonyl group bonds to nitrogen atom
● Nitrogen makes two more bonds, to H atoms or alkyl groups
● Condensation reaction 🡪 water is removed
 Addition Polymers:

What are Polymers:

● Made up of smaller subunits called monomers

● Chemical process of joining monomers to form polymers is
called polymerization
● Organic polymers are linked together by C-C, C-O, or C-N
bonds
● Addition polymers: formed from addition reactions
● Condensation polymers: formed from condensation
reactions
Properties of Plastics:

● Used as containers because they are chemically unreactive (bonds)

● Generally flexible (van der Waals)
● Can be strengthened with crosslinking
● Polystyrene, commonly referred as Styrofoam, is very flexible because of crosslinking.

Condensation Polymers: The second group of polymers are condensation polymers, formed
from the condensation reaction between monomers.

Types:

Polyester:

● Formed by condensation reactions

● Reaction between dicarboxylic acid +diol
● Ester linkage results
● Water is also a product
Polyamides:

● Polymers consisting of many amides

● Formed from condensation reactions between carboxylic acid and an amine
● Water is removed