Transcript Organic Chemistry 2014 finalzzzx

Organic Chemistry
LET’S KEEP IT SIMPLE…. FOR NOW
For Your Viewing Pleasure…
https://www.youtube.com/watch?v=ndOwa5zET8Y&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=LKGStmSxxKQ&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=lFPt6sOBFP0&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=narqglzzC44&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=2Iar8g_nO-o&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=0UHvX8lw_3Y&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=dGXkaxNkxRs&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=jhAFeCBPCRI&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=ERwybUxBbQY&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=EgX55uk-7gs&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=MQYEP2v2Or0&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=MMXsdJhepPE&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=_w7O8Co6xLc&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=wP9llcyN1_g&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=jFslN6JHA2E&list=PL7F9D3AE39F738AF8
https://www.youtube.com/watch?v=ODo0-zLzoAk&list=PL7F9D3AE39F738AF8
Organic vs. Inorganic

Historically the terms organic and inorganic were
originally applied on the basis of the source of the
chemical
 Organic
– products of living organisms
 Inorganic
– material from the non-living environment
Modern Definition of Organic
Compounds
 Today,
it is a major branch of chemistry that deals with compounds of
carbon, called ORGANIC compounds*.
 *Carbon
compounds that are exceptions and considered INORGANIC
are compounds like:
 Oxides
carbon monoxide (CO(g) ) and carbon dioxide (CO2(g) ), and
 Ionic
compounds of carbon-based ions, such as carbonate CO32-, cyanide CN-,
and carbide ions, SiC (silicon carbide)

The major source of carbon compounds is still living or previously living
things, such as plants, animals and all types of fossil fuels.
Modern Definition of Organic
Chemistry

Organic compounds are covalent compounds that generally
exist as gases, liquids or low-melting solids
(weak intermolecular forces)

Often nonpolar thus insoluble in water (like-dissolves-like)
Organic or Inorganic??
Formula
CaCO3(s)
C25H52(s)
Organic or Inorganic?
Inorganic (carbonate ion)
Organic
Ca2C(s)
CCl4(l)
CH3COOH(l)
Inorganic (carbide ion)
Organic
Organic
CO2(g)
KCN(s)
C12H22O11(s)
Inorganic (oxide)
Inorganic (cyanide)
Organic
The Special Nature of the Carbon
Atom
 Special
 Four
properties of carbon. Carbon can form:
strong bonds (4 bonding electrons)
 Long
stable chains with single, double and triple bonds
 Various
geometric structures (chains, branched chains,
rings, sheets, tubes, spheres)
Determining Lewis Formulas

So why do we care about bonding capacity?

If we know how many bonding e-’s an atom has, we can predict what structure a molecular compound will have
Atom
H
Number of
Number of
Bonding capacity
valence electrons bonding electrons
carbon
4
4
4
nitrogen
5
3
3
oxygen
6
2
2
halogens
7
1
1
hydrogen
1
1
1
I.e. Carbon can form 4 single bonds, 2 double bonds, 1 triple and 1 single, or 1 double and 2 singles
Polymers

Examples of repeating carbon chains:
Isomers

Compounds with the same number of each type of atom but different
structures (C4H10)

We will talk about this in more detail later
Importance of Organic Chemistry

Building units of all living matter: carbohydrates, proteins, fats

All foods are organic compounds

Photosynthesis is a reaction that makes carbon a part of our food. Carbon is passed along
through food chains and sugar from photosynthesis is modified and combined with other
materials.

Dead organisms are food for other organisms, or are buried in the earth and converted to
fossil fuels like peat, coal and petroleum

Petroleum is the source of fuel and starting material for plastics, fabrics and industrial
chemicals

The carbon cycle is an
illustration of the
interrelationship of all
living things with the
environment and with
technologies that
refine and use fossil
fuels

We will continually
outline the importance
of organic compounds
in our daily lives
Organization of Organic Compounds
Organic Compounds
Hydrocarbons
Hydrocarbon Derivatives
Aromatics
Aliphatics
Alkanes
Alkenes
Alkynes
Representing Organic Molecules –
Molecular Formulae
 Empirical
 indicate
Molecular Formula
total number of each atom (eg. C4H10)
 Expanded
 Indicated
Molecular Formula
groupings of atoms
(eg. CH3CH2CH2CH(CH3)CH3)
Representing Organic Molecules –
Structural Formulae
 Structural
Formulae:
 Expanded
– indicate shared pair of electrons with lines
 Condensed
– indicate the number of hydrogen atoms
bonded to each carbon atom
( CH3 CH2 CH2 CH3 )
 Line
– lines represent bonds with each end representing C
Four Types of Formulas
1.
Molecular Formulas
C5H10(g)
Not very useful for organic compounds
because so many isomers can exist
2. Structural Formulas
3. Condensed Structural Formulas
4. Line Diagrams
– end of line segment represents carbon
– it is assumed to satisfy each carbon’s octet
http://www.youtube.com/watch?v=ndOwa5zET8Y
Hydrocarbons

Organic compounds which contain only hydrogen and
carbon
Naming Hydrocarbons
PREFIXES – ROOT - SUFFIX
1 - meth-
6 - hex-
2 - eth-
7 - hept-
3 - prop-
8 - oct-
4 - but-
9 - nona-
5 - pent-
10 - dec-
Naming Organic Compounds
Aliphatic Compounds

Contain chains of carbon atoms which form homologous series

A homologous series contains a consistent increment of
change in molecular structure from one compound in the series
to the next
Naming Organic Compounds

Aliphatic Hydrocarbons – contains only hydrogen and carbon atoms

Straight line chains of carbon atoms

Alicyclic hydrocarbons have carbon atoms forming a closed ring. Still considered
aliphatic
Alkanes
Alkenes
Alkynes
Only single CC bonds
Double C-C Bond
present
Triple C-C bond
present
General
formula
CnH2n+2
General formula:
CnH2n
General formula:
CnH2n-2
Saturated
Unsaturated
Unsaturated
Aliphatic Hydrocarbons - Alkanes

Contain chains of single bonds (CnH2n+2)

Named with –ane suffix

Saturated – additional atoms can not be added w/o breaking the chain

May contain branches
(substituent added to parent chain)
Naming ALKANES
1.
Find the parent chain (the longest continuous chain of carbon
atoms). Use the appropriate root and the suffix-ane.
Naming ALKANES
1.
2.
3.
4.
Find the parent chain. Use the appropriate root and suffix.
Number the carbon atoms, starting from the end closest to the
branch(es) so that the numbers are the lowest possible
Identify any branches and their location number on the parent
chain (use the suffix –yl for branches)
Write the complete IUPAC name, following the format: (number of
location, if necessary) – (branch name) (parent chain)
2-methylheptane
Naming ALKANES

If more than one of the same branch exist, use a multiplier to show
this (di, tri). Remember to include all numbers

Draw 2,4,6-trimethylheptane
Naming ALKANES

If different branches exist, name them in alphabetical order
ethyl before methyl (e before m in the alphabet)
Naming ALKANES

If there is more than one branch of the
same type, a locating number is given to
each branch and a prefix indicating the
number of that type of branch is attached
to the name.

This numbering prefix does not affect the
alphabetical order of the branches

Draw the structural formula for
3,4-dimethylhexane
Summary of Naming Alkanes
1.
Find the parent chain. Use the appropriate root and suffix.
2.
Number the parent chain carbon atoms, starting from the end closest to
the branch(es) so that the numbers are the lowest possible
3.
Identify any branches and their location number on the parent chain (us
the suffix –yl for branches)
4.
If more than one of the same branch exist, use a multiplier (di, tri) to show
this. Remember to include all numbers
5.
If different branches exist, name them in alphabetical order
6.
Separate numbers from numbers using commas, and numbers from words
using dashes (no extra spaces)
Don’t forget…

Questions will specifically ask about
structural, condensed structural or line
structural formulas.

You must be comfortable drawing any of
the three
Practice

Write the IUPAC name for the following
2,5-dimethyl-4-propyloctane
Correct the following names:

4-ethyl-2-methylpentane

ACTUALLY 2,4-dimethylhexane

ALWAYS LOOK FOR LONGEST CHAIN!!
Correct the following name:

4,5-dimethylhexane

Actually 2,3-dimethylhexane

**Want branch numbers to be as low as possible
Try These

a.

b.
2,5,7-trimethyloctane
CYCLOALKANES

Based on evidence, chemists believe that organic carbon compounds sometimes take the form
of cyclic hydrocarbons:

Cycloalkanes: Alkanes that form a closed ring
General Formula CnH2n


Two less hydrogens are present than in straight chain alkanes because the two ends of the molecule
are joined

Are these considered saturated?? Yes, because they have only single bonds and the max amount of
hydrogen's bonded to the carbons

Cyclo-compounds will have a higher boiling point than their straight chain partners (because there is
an additional bond present)
Naming CYCLOALKANES

Cycloalkanes are named by placing the prefix cyclo in front of the alkane
name, as in cyclopropane and cyclobutane

If branches are present, treat the cycloalkane as the parent chain and
identify the branches.

Since there is no end at which to start the numbering, use the lowest numbers
possible
Name the following:
1.
2.
1,2-dimethylcyclopentane
ethylcyclohexane
**Why don’t we need a number?
Structural Isomerism

Compound with the same molecular formula but different structures

They will have different chemical and physical properties – based on their different
structures
http://www.youtube.com/watch?v=t3ionh5rtlQ
Two Types of Structural Isomers
a.
Geometric - differ only in the geometry of substituted
groups (ie. cis and trans)

There is always a new
concept to learn that extends
what you have already
learned.

In addition to the structural
isomers that you know about,
there are cis and trans isomers
Two Types of Structural Isomers
b. Stereoisomers - molecules of the same molecular structure
that differ only in the arrangement of atoms in space
(Example: mirror image, hands. wings. shoes ..)
Stereoisomers
Chemical Connection

Stereoisomers often have different biological functions. For
example, the form of glucose your
body uses for energy is D-glucose.
Your body is unable to use L-glucose at
all. You could eat all the L-glucose
you wanted and not gain weight!
Review:

Find and name all of the isomers of pentane (C5H12(l))
Aliphatic Hydrocarbons – Alkenes

-enes ; contain one or more double bond (CnH2n)

unsaturated b/c atoms can be added

since multiple bond can be at various locations isomers exist
[Note: General
formula applies only when there is a single multiple bond per
molecule]
Aliphatic Hydrocarbons – Alkynes
 -ynes
; contain one or more triple bond (CnH2n-2)
[General formula applies only when there is a
single multiple bond/molecule]
 unsaturated
 Follow
b/c atoms can be added
the same naming rules as alkenes
Naming Alkenes and Alkynes
1.
Find the parent chain. It MUST contain the multiple bond.

If the bond is a double, the suffix for the parent chain will be -ene

If the bond is a triple, the suffix for the parent chain will be –yne
2.
Count carbon atoms so that the multiple bond will be on the lowest possible
number. Indicate the number that the multiple bond falls on directly before
the suffix
3.
Name branches as before
Naming Alkenes and Alkynes

Draw the following as condensed structural formulas:
4-methylpent-2-yne
methylpropene
(why don’t we need a number?)
Naming Alkenes and Alkynes

Name the following:
3-methylbut-1-ene
5-methylhex-2-ene
Naming Alkenes and Alkynes
It is possible for a molecule to have more than one double bond. These
are called alkadienes and have the same general formula as alkynes
(CnH2n-2)
4.

If this is the case, indicate both numbers where the
change the suffix to –diene.
a) Draw buta-1,3-diene:
b) What is the IUPAC name for the following:
buta-1,2-diene
double bond is formed, and
Cycloalkenes and -ynes

The rules for naming cycloalkenes and cycloalkynes are the same as
naming cycloalkanes

The numbering for the carbon atoms begins with the double bond; the carbons of
the double bond are carbons 1 and 2; lowest numbers possible

Draw 3-methylcyclohexene as a condensed structural formula
Aromatics

Originally, organic compounds with an aroma or odour were
called aromatic compounds

Now, aromatics refer to compounds containing a benzene-ring
structure
 Benzene’s
formula is C6H6, which would suggest a highly unsaturated and
reactive compound
 Benzene
is actually quite unreactive and is considered more stable than
alkenes and alkynes
 Did
You Know?? Benzene is a carcinogen and is found naturally in
petroleum – why would this be a problem?
What do we know about benzene?

Formula is C6H6 (3D link)

Unreactive – so no true double or triple bonds

Carbon-carbon bonds are the same length and strength

Each carbon is bonded to a hydrogen

So what does benzene look like??
The three double bonds resonate resulting in
an overall bond length somewhere in
between a single and a double bond,
explaining benzene’s stability
We will use this
line structural
formula to
represent
benzene in
compounds
Common Aromatic Compounds

Include Aspirin and Vanillin (one of the flavour molecules in vanilla)
 You
will notice many aromatic molecules are often depicted using a
condensed structural formula except for the benzene ring, which is
shown as a line structural formula.
 This
combination is commonly used by chemists, and we will use this
method when drawing aromatics.
Benzene as a Branch

When benzene is added to a hydrocarbon chain as a substituent
molecule it is called phenyl
 Example:
3-methyl-3,5-diphenylhexane
Naming Aromatics
1.
If an alkyl branch is attached to a benzene ring, the compound is
named as an alkylbenzene.

Alternatively, the benzene ring may be considered as a branch of a large
molecule: in this case, the benzene ring is called a phenyl branch. Which
has a phenyl branch?
An alkylbenzene
Contains a phenyl
branch
Naming Aromatics
If more than one alkyl branch is attached to a benzene ring, the
branches are numbered using the lowest numbers possible, starting
with one of the branches.
2.

Given the choice between two sets of lowest numbers, choose the set that is in both
numerical and alphabetical order
1-ethyl-2,4-dimethylbenzene
3-phenyl-4-propyloctane
Practice Naming Aromatics
Draw 1,2-dimethylbenzene


Are there any isomers of this compound?
1,2dimethylbenzene
o-dimethylbenzene

1,3dimethylbenzene
m-dimethylbenzene
1,4dimethylbenzene
p-dimethylbenzene
There is also classical way of naming these isomers. The arrangements are denoted
by the prefixe:s ortho (o), meta (m) and para (p). These names are still used in
industry so you may encounter them in other references.
Practice Naming Aromatics

Draw the line structural formula for 1-ethyl-3-methylbenzene

Draw the line structural formula for 2-phenylpentane
Practice Naming Aromatics

Draw 3-phenylpent-2-ene

Name the following
propylbenzene
Why is no number needed?
Are the hydrogen’s
wrong??
Summary

We have now learned about both aliphatic and aromatic hydrocarbons.
You will need to be comfortable naming all of the following:
Organic Halides

Organic compounds where one or more hydrogen has been replaced with
halogens (F, Cl, Br, I)

Common example: CFC (chlorofluorocarbons)
Nomenclature is similar to naming branch chains of hydrocarbons, but the branch name used is
based on the halogen used [Classification as 1o, 2o or 3o is based on the
C to which the halogen is directly attached]

chloro-, fluoro-, bromo-, iodo

Involved in addition, substitution and
elimination reactions
Halides
Organic Halide

What do you need to know about organic halides?

May by polar or nonpolar molecules or may have a relatively nonpolar
(hydrocarbon) end and a polar (halide) end (**Remember
Electronegativity differences)

Have higher boiling points than similar hydrocarbons

Have very low solubility in water but higher solubility than similar
hydrocarbons

Are typically good solvents for organic materials such as fats, oils, waxes,
gums, resins or rubber

Usually toxic or ecologically damaging (DDTs and PCBs)
Practice

Draw 1,2-dichloroethane

Draw 2,2,5-tribromo-5-methylhexane
Practice
Name the following:

CH2Cl2

1,2-dibromoethene

chlorobenzene
Alcohols

An alcohol is an organic compound that contains the –OH functional group
(hydroxyl)

General formula is R-OH (R = rest of molecule)

Alcohols are classified as primary, secondary or tertiary depending on the
number of carbons bonded to the carbon that contains the hydroxyl group
[Note: not a hydroxide ion b/c oxygen is covalently bonded to
carbon]
Common Alcohols


Methanol (also called wood alcohol) is extremely toxic, causing death and
blindness
Ethanol (also known as grain alcohol) is the
alcohol found in alcoholic beverages and is
used in the production of vinegar

Gas line antifreeze, windshield de-icer,
windshield washer fluid – all contain methanol
Naming Alcohols

Locate the longest chain that contains an –OH group attached to one of
the carbon atoms. Name the parent alkane

Replace the –e at the end of the name of the parent alkane with –ol (i.e.
butane becomes butanol)

Add a position number before the suffix –ol to indicate the location of the –
OH group

REMEMBER to number the main chain of the hydrocarbon so that the
hydroxyl group has the lowest possible position number
propan-1-ol
Naming Alcohols

If there is more than one –OH group (called polyalcohols), leave the –e in the name of the
parent alkane and put the appropriate prefix before the suffix –ol (i.e. diol, triol, tetraol)

5. Name and number any branches on the main chain. Add the names of these branches to
the prefix.

Draw 2,3-dimethylbutan-2-ol
Degrees of Alcohols
 Primary
 The
 R-CH2-OH
carbon that the
hydroxyl group is attached
to is bonded to one other
carbon atom
Degrees of Alcohols
R
|

Secondary -> R – CH – OH

The carbon that the hydroxyl
group is attached to is
bonded to two other carbon
atoms
Degrees of Alcohols
R
|

Tertiary  R – C – OH
|
R

The carbon that the hydroxyl group is
attached to is bonded to three other C
atoms
Practice Naming Alcohols
Draw line structural formulas for:

1. cyclohexanol

2. phenol

3. The three isomers of C5H11OH that are pentanols
These are the
only two cyclic or
aromatic alcohols
you will need to
know as they get
very complicated
Carboxylic Acid

A carboxyl group is composed of a carbon atom double bonded to an
oxygen atom and bonded to a hydroxyl group (-COOH)

Note: Because the carboxyl group involves three of the carbon atom’s
four bonds, the carboxyl is always at the end of a carbon chain or branch

Examples:
Naming Carboxylic Acids

Name the parent alkane

Replace the –e at the end of the name of than parent alkane with –oic
acid

The carbon atoms of the carboxyl group is always given position number
1. Name and number the branches that are attached to the compound.

Draw 3-methylbutanoic acid
Remember COOH or HOOC
can also represent the
carboxyl group
Naming Carboxylic Acid

Draw trichloroethanoic acid (key ingredient in chemical peels)

Draw 3-propyloctanoic acid
Esters

The reaction between a carboxylic acid and an alcohol produces an ester molecule and a molecule
of water

This reaction is known as a condensation or esterification reaction

The ester functional group –COO– is similar to that of a carboxylic acid, except that the H atom of the
carboxyl group has been replaced by a hydrocarbon branch.

Esters are responsible for natural and artificial fragrance and flavourings in plants and fruits.
Esters


The formula for an Ester is: R-COO-R’
 R=
carboxylic acid
 R’=
alcohol
Tend to have higher m.p/b.p than carboxylic
acids
Esters

In naming an ester you have to recognize that an ester has 2 distinct parts.
The main part contains the C=O group which comes from the parent acid.

The second part is the alkyl group.
Naming Esters

Identify the main part of the ester, which contains the C=O group. This part comes from the
parent acid.

Begin by naming the parent acid but replace the –oic acid ending of the name with –
oate. (propanoic acid becomes propanoate)

The second part is the alkyl group that is attached to the single oxygen atom. Name this as
you would any other alkyl group (in this case = methyl)

Put the names together. Note that esters are named as two words.
Naming Esters

Name the following ester and the acid and alcohol from which it can be prepared.
A strong acid catalyst, such as
H2SO4(aq) is used along with some
heating to increase the rate of the
organic reaction
Tip: The branch attached to the oxygen (of the –COO) comes first in the name,
the chain attached to the carbon (of the –COO) comes second
The Structure and Odour of Some Esters
Ester Name
Structure
Odour
Methyl acetate
Glue
Ethyl acetate
Nail Polish Remover
Propyl ethanoate
Pear
Pentyl pentanoate
Apple
ORGANIC Unit Review
Organic or Inorganic??
Formula
CaCO3(s)
C25H52(s)
Organic or Inorganic?
Inorganic (carbonate ion)
Organic
Ca2C(s)
CCl4(l)
CH3COOH(l)
CO2(g)
Inorganic (carbide ion)
Organic
Organic
Inorganic (oxide)
KCN(s)
C12H22O11(s)
Inorganic (cyanide)
Organic
Four Types of Formulas
1.
Molecular Formulas
2.
Structural Formulas
1.
Condensed Structural Formulas
2.
Line Diagrams
– end of line segment represents carbon
organic
so many
C5H10(g)
Not very useful for
compounds because
isomers can exist
– it is assumed to satisfy each carbon’s octet
Naming Organic Compounds

Aliphatic Hydrocarbons – contains only hydrogen and carbon atoms

Straight line chains of carbon atoms

Alicyclic hydrocarbons have carbon atoms forming a closed ring. Still considered
aliphatic
Alkanes
Alkenes
Alkynes
Only single C-C
bonds
Double C-C Bond
present
Triple C-C bond
present
General formula
CnH2n+2
General formula:
CnH2n
General formula:
CnH2n-2
Saturated
Unsaturated
Unsaturated
Summary of Naming Alkanes
1.
Find the parent chain. Use the appropriate root and suffix.
2.
Number the parent chain carbon atoms, starting from the end closest to the
branch(es) so that the numbers are the lowest possible
3.
Identify any branches and their location number on the parent chain (us
the suffix –yl for branches)
4.
If more than one of the same branch exist, use a multiplier (di, tri) to show
this. Remember to include all numbers
5.
If different branches exist, name them in alphabetical order
6.
Separate numbers from numbers using commas, and numbers from words
using dashes (no extra spaces)
CYCLOALKANES

Based on evidence, chemists believe that organic carbon compounds sometimes
take the form of cyclic hydrocarbons:

Cycloalkanes: Alkanes that form a closed ring
General Formula CnH2n


Two less hydrogens are present than in straight chain alkanes because the two ends
of the molecule are joined

Are these considered saturated?? Yes, because they have only single bonds and the
max amount of hydrogen's bonded to the carbons

Cyclo-compounds will have a higher boiling point than their straight chain partners
(because there is an additional bond present)
Naming Alkenes and Alkynes
1.
Find the parent chain. It MUST contain the multiple bond.

If the bond is a double, the suffix for the parent chain will be -ene

If the bond is a triple, the suffix for the parent chain will be –yne
2.
Count carbon atoms so that the multiple bond will be on the lowest possible
number. Indicate the number that the multiple bond falls on directly before
the suffix
3.
Name branches as before
Naming Alkenes and Alkynes
4.
It is possible for a molecule to have more than one double bond.
These are called alkadienes and have the same general formula as
alkynes (CnH2n-2)

If this is the case, indicate both numbers where the
and change the suffix to –diene.
a) Draw buta-1,3-diene:
b) What is the IUPAC name for the following:
buta-1,2-diene
double bond is formed,
Structural Isomerism

Compound with the same molecular formula but different structures

They will have different chemical and physical properties – based on their different
structures
 What
do we know about benzene?

Formula is C6H6 (3D link)

Unreactive – so no true double or triple bonds

Carbon-carbon bonds are the same length and strength

Each carbon is bonded to a hydrogen

So what does benzene look like??
The three double bonds resonate resulting in an
overall bond length somewhere in between a single
and a double bond, explaining benzene’s stability
We will use this line
structural formula to
represent benzene
in compounds
Practice Naming Aromatics

Draw the line structural formula for 1-ethyl-3-methylbenzene

Draw the line structural formula for 2-phenylpentane
Practice Naming Organic Halides

Name the following:
CH2Cl2
dichloromethane
1,2-dibromoethene
Bonus: Try 1,2-dibromo-1,2-dichloroethene
chlorobenzene
Alcohols

An alcohol is an organic compound that contains the –
OH functional group (hydroxyl)
 General

formula is R-OH (R = rest of molecule)
Alcohols are classified as primary, secondary or tertiary
depending on the number of carbons bonded to the
carbon that contains the hydroxyl group
Naming Alcohols
1.
Locate the longest chain that contains an –OH group attached to one of the
carbon atoms. Name the parent alkane
2.
Replace the –e at the end of the name of the parent alkane with –ol (i.e.
butane becomes butanol)
3.
Add a position number before the suffix –ol to indicate the location of the –OH
group

REMEMBER to number the main chain of the hydrocarbon so that the hydroxyl
group has the lowest possible position number
propan-1-ol
Naming Alcohols
If there is more than one –OH group (called polyalcohols), leave the –e in
the name of the parent alkane and put the appropriate prefix before the
suffix –ol (i.e. diol, triol, tetraol)
4.
5. Name and number any branches on the main chain. Add the names of
these branches to the prefix.

Draw 2,3-dimethylbutan-2-ol
Carboxylic Acids

A carboxyl group is composed of a carbon atom double bonded to
an oxygen atom and bonded to a hydroxyl group (-COOH)

Note: Because
the carboxyl group involves three of the carbon atom’s
four bonds, the carboxyl is always at the end of a carbon chain or
branch
Examples:
methanoic acid
ethanoic acid
Carboxylic acids are
weak organic acids
Naming Carboxylic Acids
1.
Name the parent alkane
2.
Replace the –e at the end of the name of than parent alkane with –oic
acid
3.
The carbon atoms of the carboxyl group is always given position number 1.
Name and number the branches that are attached to the compound.
Draw 3-methylbutanoic acid
Remember COOH or HOOC
can also represent the
carboxyl group
HOOC
Esters

The reaction between a carboxylic acid and an alcohol produces an ester
molecule and a molecule of water

This reaction is known as a condensation or esterification reaction
The ester functional group –COO– is similar to that of a carboxylic acid, except
that the H atom of the carboxyl group has been replaced by a hydrocarbon
branch.
 Esters are responsible for natural and artificial fragrance and flavourings in plants
and fruits.

Naming Esters

Name the following ester and the acid and alcohol from
which it can be prepared.
butanoic acid
ethyl butanoate
ethanol
A strong acid catalyst,
such as H2SO4(aq) is used
along with some heating
to increase the rate of the
organic reaction
water
Tip: The branch attached to the oxygen (of the –COO) comes first in the
name, the chain attached to the carbon (of the –COO) comes second
Sometimes we need to stop and
think…

http://www.youtube.com/watch?v=r-Yn4b9iClE
Physical Properties of Simple Hydrocarbons
Alkanes
Non-polar molecules
Only intermolecular forces are London Force
Boiling point and melting point increase with number of carbons
All insoluble in water (like dissolves like) – nonpolar and polar don’t mix
1-4Cs = gas, 5-16Cs = liquid 17 and up = solid at SATP
Alkenes
Non-polar molecules, therefore insoluble in water
Boiling points slightly lower than alkanes with the same number of
carbons due to less electrons (unsaturated), resulting in lower London
Forces
Alkynes
Non-polar molecules, therefore insoluble in water
Higher boiling points than alkanes and alkenes with similar C #s
Accepted explanation: Linear structure around triple bond allows electrons
to come closer together than in alkanes/enes, resulting in greater London
Force
Branching
The more branching, the less significant the London Force (~lower b.p.)
- more surface area in straight chain hydrocarbons allows more
separation of charge, resulting in greater London Force
- see Table #3 pg. 378 (i.e. pentane (with 5Cs) has a b.p. of 36oC
which is much higher than dimethylpropane (5Cs) -12oC) = because
branching decreased the strength of the London force
Physical Properties of Hydrocarbon Derivatives
Alcohols
Much higher boiling points than hydrocarbons (1-12Cs are liquids at SATP)
due to hydrogen bonding between hydroxyl groups of adjacent molecules
Small alcohols are totally miscible in water, but the larger the hydrocarbon
part of the alcohol (nonpolar part), the more nonpolar the alcohol is
Carboxylic
Acids
Like alcohols they have hydrogen bonding, but is more significant due to the
C=O. This means greater bps and solubility than alcohols with same number
of Cs.
Carboxylic acids with 1-4Cs are
completely miscible in water
Esters
Compound
Boiling Point (oC)
butane
-0.5
butan-1-ol
117.2
butanoic acid
165.5
Fruity odour in some cases
Polar but they lack the –OH bond therefore do not have hydrogen bonding, so
lower bps than both alcohols and carboxylic acids
Esters with few carbons are polar enough to be soluble in water
Application Question

Predict the order of increasing boiling points for the following
compounds, and give reasons for your answer.
butan-1-ol
pentane
1-chlorobutane

Answer: (Lowest b.p.): pentane, 1-chlorobutane, butan-1-ol
Why? All molecules have a similar number of electrons. Pentane has the
lowest boiling point, because it is non-polar so will only have London forces
between the molecules. 1-chlorobutane is polar so will have dipole-dipole
forces as well as London forces. Butan-1-ol has the highest boiling point
because its molecules will have all three intermolecular forces, most
importantly, hydrogen bonding
Sample Question

Predict the relative order of boiling points of the following compounds (lowest to
highest). Explain your reasoning.
butanol
but-1-ene
cyclobutane
butanoic acid
butane
Lowest -------------------------------------------------------------> Highest
but-1-ene butane cyclobutane butanol butanoic acid
Reasoning: but-1-ene has lower LF’s for than butane because it is unsaturated, cyclobutane
has an additional bond because cyclic, butanol has H-bonding, butanoic acid has
stronger H-bonding)

Which would be soluble in water?

Butanol and butanoic acid – because they are the only polar molecules and like dissolves
like!
Physical Refining of Fossil Fuels
Let’s Consider…
http://nbcpolitics.nbcnews.com/_news/2014/01/31/22524683-report-keystone-pipeline-would-haveminimal-environmental-impact
http://www.youtube.com/watch?v=Ea14eufiEq8
http://www.youtube.com/watch?v=KZ96Ss47Fv0
http://www.ted.com/talks/garth_lenz_images_of_
beauty_and_devastation.html
http://www.theglobeandmail.com/news/newsvideo/video-al-gore-calls-alberta-oil-sands-anopen-sewer/article11732578/
http://www.youtube.com/watch?v=mGAFnKXrTSs
http://www.ethicaloil.org/
http://vimeo.com/40781438
http://www.dailymotion.com/video/xiqql0_jamescameron-to-see-oil-sands-for-himself_news
http://www.youtube.com/watch?v=mNW_ms35JKE
Crude Oil Refining

Crude oil is a complex mixture of hundreds of thousands of
compounds, all of which have different boiling points
 We
can take advantage of these different b.p.’s and physically separate
the different components using heat
 This
process is called fractional distillation or fractionation

A fractional distillation tower contains
trays positioned at various levels.

Heated crude oil enters near the
bottom of the tower.

The bottom is kept hot, and the
temperature gradually decreases
toward the top of the tower.

As compounds cool to their boiling
point, they condense in the cooler
trays. The streams of liquid (called
fractions) are withdrawn from the
tower at various heights along the
tower.
Electronic Visual

A more detailed look…

The vaporized components of the crude
oil rise and gradually cool.

To get from one level to the next, the
vapours are forced to bubble through the
liquid condensed in each tray.

The figure shows the bubble caps used to
allow this to happen.


If a gas cools to its boiling point, it will
condense and be piped out through the
draining tube
Crude oil is heated in the fractionation tower
without air being present to reduce the risk of
mixtures starting to burn or explode
Q: How does the number of carbon atoms in a hydrocarbon chain
affect its boiling point?
 Smaller molecules have fewer electrons, so weaker London forces
compared with larger molecules. The fractions with higher boiling points
are found to contain much larger molecules
http://www.youtube.com/watch?v=PYMWUz7TC3A
http://www.youtube.com/watch?v=Xsqlv4rWnEg
Cracking

Cracking: large hydrocarbons are broken into smaller fragments

Historically, thermal cracking used extremely high temperatures but created large quantities of
solid coke.

Now, catalytic cracking uses a catalyst to speed up the reaction and produce less residual
products like tar, asphalt and coke

Example: C17H36(l)  C9H20(l) + C8H16(l) + C(s)
larger molecules  smaller molecules + carbon

In 1960, hydrocracking was developed, which combines catalytic cracking and hydrogenation
and produces no coke.

Example: C17H36(l) + H2(g)  C9H20(l) + C8H16(l)
larger molecule + hydrogen  smaller molecules
http://www.youtube.com/watch?v=VofKBcdZtjo
Oil Refining
The refining of crude oil can be divided into two main categories:
1. Physical Processes

Fractional Distillation: see previous slides
 Solvent Extraction: solvent is added to selectively dissolve and remove an impurity or
to separate a useful product from a mixture

2.
Chemical Processes


Cracking – larger molecules are broken down into smaller ones
Reforming – large molecules are formed from smaller ones
These chemical processes are needed because fractional distillation does not produce
enough of the hydrocarbons that are in demand (i.e. gasoline) and produces too
much of the heavier fractions
Catalytic Reforming and Alkylation

Catalytic Reforming: improves the quality of the gasoline
aliphatic molecule  aromatic molecule + hydrogen

Alkylation: increases the branching; improves the quality of the fuel
aliphatic molecule  more branched molecule

(AKA: isomerization because it converts molecules into a branched isomer)
Combustion Reactions

Burning of hydrocarbons in the presence of oxygen

Complete Combustion: abundant supply of oxygen; products are carbon
dioxide, water vapour and heat


Example: C3H8(l) + 5O2(g)  3CO2(g) + 4H2O(g)
Incomplete Combustion: limited supply of oxygen; products are carbon
monoxide, soot (pure carbon) or any combination of carbon dioxide, carbon
monoxide and soot in addition to water vapour and heat
 Example: 2C8H18(l) + 17O2(g)  16CO(g) + 18H2O(g)
OR
2C8H18(l) + 9O2(g)  16C(s) + 18H2O(g)
** Assume complete combustion unless specified otherwise
Balancing FYI
Example:
2C8H18(l) + 17O2(g)  16CO(g) + 18H2O(g)
Can also be balanced using a fraction (you need to be comfortable using this method) – divide
each number by 2
C8H18(l) + 17/2 O2(g)  8CO(g) + 9H2O(g)
Example:
2C8H18(l) + 9O2(g)  16C(s) + 18H2O(g)
can also be balanced as …
C8H18(l) + 9/2 O2(g)  8C(s) + 9H2O(g)
Combustion Reactions

Products depend on O2 present:

Excess (complete


CO2(g) + H2O (g) + E
Limited (hypoxic)


combustion)
CO (g) + H20 (g) + E
Very limited (anoxic)

C (s) + H20 (g) + E
[Note: no useful organic compounds]
Greenhouse Gases

Carbon dioxide gas, which is produced
during the combustion of fossil fuels, is a
greenhouse gas.

The production of fuel sources and the
burning of fossil fuels has had a damaging
impact on the environment
Hydrocarbon Reactions
1.
Addition
alkenes and alkynes + H2(g)  alkanes (hydrogenation)
alkenes and alkynes + HX (or X2)  organic halides
2.
Substitution
alkanes and aromatics + X2  organic halides
3.
Elimination
alcohols  alkenes + water (dehydration)
organic halides + OH-  alkenes + halide ion + water
4.
Esterification (already covered)
carboxylic acid + alcohol  ester + water
Addition Reactions

There are four types of addition reactions, each characterized by a
reaction with a different type of molecule:
1) Hydrogenation
2) Hydration
3) Addition of Halogens, Hydrogen Halides and Acids
4) Multiple Additions
Addition Reactions: reaction of alkenes and alkynes with
hydrogen gas, a halogen compound, or a hydrogen
halide compound.
1.

Addition reactions usually occur in the presence of a
catalyst
a)
Addition with H2(g) (also called hydrogenation)
1.
Addition Reactions: reaction of alkenes and alkynes with
hydrogen gas, a halogen compound, or a hydrogen halide
compound
b)
Addition of a halogen
1,2-dichloroethane is a useful solvent
and is used to produce chloroethene, the
monomer used to make PVC.
Since addition reactions involving
multiple bonds are very rapid, the
alkene product 1,2-dibromoethene can
easily undergo a second addition step
to produce 1,1,2,2-tetrabromomethane.
Excess bromine promotes this second
step.
1.
Addition Reactions: reaction of alkenes and alkynes with hydrogen gas, a
halogen compound, or a hydrogen halide compound
Addition of an HX (hydrogen halide) molecule
c)

Show both possible isomers when predicting the products
The addition of hydrogen halides (HF, HCl, HBr or HI) to unsaturated compounds can produce
structural isomers, since the hydrogen halide molecules can add in different orientations. However,
the type of isomers produced are not always equal.
For example only a tiny amount of 1-chloropropane is produced compared to 2-chloropropane in
the above reaction.
Hydrogenation

Conversion of unsaturated hydrocarbons to saturated
hydrocarbons

Hydrogenated fats are used in stick margarine, fast foods,
commercial baked goods (donuts, cookies, crackers), processed foods,
and fried foods.
Trans fatty acids

Manufactured fats created during
a process called hydrogenation
(aimed at stabilizing polyunsaturated oils to
prevent them from becoming rancid and to
keep them solid at room temperature.)

They may be dangerous for the
heart and may pose
for cancers.
a risk
Example: Converting ethyne
Example

Write a structural formula equation for the production of
chloroethene (vinyl chloride) from ethyne (acetylene),
hydrogen chloride and a HgCl2 catalyst.
Markovnikov’s Rule

H-atom of the small molecule being added attaches to the
carbon involved in the double bond that is bonded to the
most H atoms
Hydration

During this type of addition reaction, water is added to an unsaturated
hydrocarbon, resulting in the production of an alcohol.

Use structural diagrams to show the hydration of prop-1-ene that results
in the production of propan-1-ol
Addition of Halogens, Hydrogen Halides and
Acids

During this type of addition reaction, alkenes and alkynes are reacted
with substances such as Fluorine, Chlorine and Hydrochloric acid.

Use structural diagrams to show the addition of bromine to but-2-ene
during an addition reaction
Multiple Additions

When there are two or more molecules being added to a hydrocarbon,
the maximum number of bonds that can be broken in order to add the
atoms in two.

Most additions of multiple molecular groups are reactions with
aromatics or alkynes

Use structural diagrams to show the addition reaction resulting in the
production of 1,1,2,2-tetrafluoropropane by adding two molecules of
fluorine gas to propyne
Practice Addition Reactions

For each of the following questions, draw condensed structural diagrams
and name all products
+ bromine
1,2-dibromoethane
1.
ethene
2.
hydrogen chloride + ethene 
3.
3-methylbut-1-yne + excess hydrogen 

__
chloroethane

2-methylbutane
2.
Substitution Reactions – breaking of a C-H bond in an alkane or an
aromatic ring and replacing it with another atom or group of atoms

Usually occur slowly at room temperature, so light may be necessary as a
catalyst

Often substitutes a halogen for a hydrogen

No change in saturation
Propane contains hydrogen atoms bonded to end carbons and the middle carbon
atom, so two different products (isomers) are formed, in unequal proportions
2.
Substitution Reactions – breaking of a C-H bond in an alkane
or an aromatic ring and replacing it with another atom or
group of atoms
Benzene rings are stable, like alkanes, so they react slowly with halogens, even in the
presence of light.
Would all three isomers be created equally?
As with alkanes, further substitution can occur in benzene rings, until all hydrogen atoms are
replaced by halogen atoms (in the presence of excess halogens)
NO
Practice Substitution Reactions

1.
For each of the following questions, draw condensed
structural diagrams and name all products
propane + fluorine
 1-fluoropropane + 2-fluoropropane + hydrogen fluoride
H-F
F-F
2.
ethane
+
chlorine

chloroethane + hydrogen chloride
3.
Elimination Reactions – involves eliminating atoms or groups of atoms from
adjacent carbon atoms; decreases the level of saturation
a)
Alkane cracked into an alkene (uses high temperatures)
a)
Alcohol is reacted with a catalyst to produce an alkene and water (dehydration
– removes a water molecule from the alcohol)
a)
Alkyl halide reacts with a hydroxide ion
(OH-) to produce an alkene
(dehydrohalogenation – removes a
hydrogen and halogen atom)
Practice Elimination Reactions

Write a structural formula equation for the preparation of but-2-ene
from chlorobutane, in the presence of a strong base

Write a structural formula equation for the preparation of but-2-ene
from butan-2-ol
Esterification Reactions aka condensation

Reaction between carboxylic acids and alcohols

The production of an ester linkage by reacting a carboxylic acid and an
alcohol
Example
 Carboxylic
acid + alcohol  ester + water
http://www.youtube.com/watch?v=n1nyHeDusHk
Polymerization

Polymers are large molecules made of
chains of monomers, small molecules that link
together.

Polymerization is the formation of
polymers from these small units

Polymers can occur naturally (proteins,
carbohydrates) and can be synthesized
(nylon, Teflon, polyethylene)

They play an integral part in the function
of life systems and have revolutionized the
way society functions
http://www.nbclearn.com/portal/site/learn/chemistry-now/bulletproof-chemistry-kevlar
Addition Polymerization

Many plastics (synthetic polymers) are made by this process

The polymerization process is initiated with a free radical (a species with an
unpaired electron). The free radical attacks and breaks the double bond
forming a new free radical that attacks another monomer

Addition Polymerization always results in one product, the
polymer

Requires unsaturated hydrocarbon monomers and bond
saturation occurs when the polymer is made

Common polymers produced by addition polymerization:
Things to know about addition polymers…

The polymer names end in –ene (i.e. polystyrene, polypropene). Does this mean they
have double bonds?


No, the double bonds are saturated by adjacent monomers, as the polymer is made.
The name refers to the starting monomer (i.e. polyethene is started by the monomer
ethene)
What properties make Teflon a good product for non-stick materials?

Teflon is made up of C-F bonds which are very strong (not C-H bonds). These very
strong bonds make the Teflon highly unreactive (non-sticking), it has a high melting
point and it has a slippery surface
Condensation Polymerization

Monomers combine to form a polymer and a biproduct. Each time a bond forms between monomers,
small molecules, such as water, ammonia, or HCl are
“condensed” out.

The polymerization of nylon:
• For condensation polymerization
to occur, monomers must be
bifunctional, meaning they have
at least two functional groups.
• If they only had one functional
group, then only one bond would
form.
Condensation Polymerization

Condensation polymerization also produces natural polymers, called
proteins.

Amino acids (monomers) polymerize to make peptides (short chains of
amino acids) or proteins (long chains of amino acids)
Comparison of Addition and
Condensation Polymerization
Addition
Condensation

Needs a double or triple
bond in the monomer

Needs bifunctional monomers
(have two functional groups)

Produces only one
product, the polymer

Produces two products: the
polymer and the biproduct
(water, ammonia or HCl)
Polyester

When a carboxylic acid reacts with an alcohol in an esterification
reaction, a water molecule is eliminated and a single ester molecule is
formed.

This esterification reaction can be repeated so many esters are joined in a
long chain… a polyester

This is created using a dicarboxylic acid (an acid with a carboxyl group at
each end) and a diol (an alcohol with a hydroxyl group at each end)

The ester linkages are formed end to end between alternating acid and
alcohol molecules
CHEMISTRY 30 ORGANIC REVIEW