Block 1 Foundations

CHEM110/Block 1/Foundations/2020 1
CHEM110 2020
CHEMISTRY OF THE LIVING WORLD
BLOCK 1: FOUNDATIONS
Unit 1: INTRODUCTION TO BONDING
Unit 2: ISOMERISM
Unit 3: NOMENCLATURE
Unit 4: MECHANISM AND REACTIVITY
Lecturers
Dr Kaitlin Beare (KDB)
email: CHEM110@auckland.ac.nz
Building-Room: 302-847
This handout should be brought to all lectures.

At the end of each unit a problem sheet is attached. Answers to these problems are available on
Canvas under Foundations (Block 1) / Lecture Resources.
Please fill in the section below. Should you misplace this handout it will assist us in returning it
to you. Anyone finding this handout should take it to Chemistry Reception, Level 6 of Building
302 (Science Centre).
Name:
Laboratory Day and Time: Bench Number:
© School of Chemical Sciences The University of Auckland

Block 1 is primarily focused on the language of chemistry - how to we name or draw organic
molecules? How do we describe what happens when a reaction occurs? How do we describe
the three dimensional shape of molecules? It also introduces the core principles of bonding in
organic molecules and shows how molecular shape and bonding (electronic) structure can be
used to explain both the physical properties and reactivity of molecules. It is the foundation on
which the remainder of the course is built.
At the end of block 1, you should be able to:

• Use standard notations to describe bonding in organic molecules.
• Use standard naming and drawing conventions to depict organic molecules.
• Recognise and describe different types of isomerism (constitutional, conformational and
configurational) in organic molecules.
• Predict the physical properties and behaviours of organic molecules based on their physical
and electronic structure.
• Organise organic reactions by ‘type’.
• Describe the components of a reaction mechanism, and explain why these are used by
organic chemists.
• Use curly arrow notation to show the steps in a reaction mechanism.

UNIT 1 - INTRODUCTION TO BONDING
1.1 BONDING IN ORGANIC COMPOUNDS
1.1.1 Carbon Makes Excellent Scaffolds
Carbon makes 4 bonds.
• Carbon has 6 electrons (1s2 2s2 2p2)
– 4 valence electrons
– requires 4 more for a full shell (8) 6 12.01
– forms 4 covalent bonds
– mid-range electronegativity
C
carbon
• C-C and C-H bonds are strong and unreactive
• C can bond: – to itself
– to metals
– to heteroatoms (atoms other than C or H)
• Geometrically flexible – forms chains, rings, multiple bonds.
Nitrogen makes 3 bonds (when uncharged).
• Nitrogen has 7 electrons (1s2 2s2 2p3)
7 14.01
– requires 3 more for a full shell (8)
– forms 3 covalent bonds and has 1 lone pair N
– more electronegative than carbon nitrogen
– lone pairs are available for reaction
Oxygen makes 2 bonds (when uncharged).
• Oxygen has 8 electrons (1s2 2s2 2p4)
– 6 valence electrons 8 16.00

– forms 2 covalent bonds and has 2 lone pairs
O
oxygen
– more electronegative than nitrogen
– lone pairs are less available for reaction
Fluorine makes 1 bond
• Fluorine has 9 electrons (1s2 2s2 2p5) 9 19.00
F
fluorine
– forms 1 covalent bonds and has 3 lone pairs
– very electronegative
– lone pairs are not available for reaction
Hydrogen makes 1 bond 1 1.008
H
• Hydrogen has 1 electron (1s1)
– 1 valence electron
– requires 1 more for a full shell (2) hydrogen
– forms 1 covalent bond
– less electronegative than carbon.

Pre-Lecture Reading (Lecture 2)

There is no pre-lecture reading for Lecture 1. However, we encourage you to attempt the
electronic configurations exercise on BestChoice as preparation for this lecture. The following
pre-reading is intended for Lecture 2.
1.1.2 Bonding Arrangements – The Basics

Carbon can be joined to other appropriate atoms by a single, double or triple bond (but nor
quadruple bond) and must total exactly 4 bonds.
e.g.
H O
H C H C O C O H C N
H H H
Nitrogen can also form single, double and triple bonds.

Oxygen can form single and double bonds.
Hydrogen/halogens can only form single bonds.
The valences/bonding possibilities for elements relevant to this course are:
Element(s) Valence* Bonding possibilites for neutral molecules
C C C C
C 4
N 3 N N N
O 2 O O
H, halogens (X) 1 H X
*Valence – number of bonds to an atom in a stable, neutral (uncharged) molecule.
1.1.3 Functional Groups

In organic compounds only a small number of bonding arrangements are routinely seen
involving anything other than the saturated (no multiple bonds) hydrocarbon skeleton. These
arrangements are known as functional groups.
A functional group is a recognizable arrangement of atoms that is characteristic of a

class of molecules. Compounds containing the same functional group can be expected to
display similar reactivity.
For example, all molecules containing the C-OH functional group are alcohols.
CH3OH
CH3CH2OH
CH3CH2CH2OH
CH3CH2CH2CH2OH
We can write a general formula for alcohols ROH (R = and alkyl group).

1.1.4 Common Functional Groups and Nomenclature
“Structure” Compound Nomenclature (excl. aromatics)
class Prefix Stem Suffix
A: That are part of
the molecular alkene alk ene
framework
─C≡C─ alkyne alk yne
B: Containing oxygen
alcohol alkan ol
1. With only
carbon-oxygen ether (di)alkyl ether
single bonds
2. With only aldehyde alkan al

carbon-oxygen
double bonds
ketone alkan one
3. With both carboxylic alkan oic acid

carbon-oxygen acid
single and
double bonds alkyl alkan oate
ester ♦
acid alkan oic

anhydride ♦ anhydride
C: Containing nitrogen amine#
(primary) alkyl amine
─C≡ N nitrile alkane nitrile

(or cyanide)
D: Containing nitrogen
and oxygen amide ♦
alkan amide
(primary)
E: Containing halogen
alkyl halide halo alkane
X = F, Cl, Br, I
F: Containing oxygen acyl halide ♦

alkan oyl halide
and halogen X usually Cl or Br
G: Containing sulfur thiol alkane thiol

[-SH group]
Where no specific atom or group is given at the end of a bond in the “structure” column the
valence may be completed by a hydrogen atom or the carbon of an alkyl/aryl group. We will
look at the formal naming rules for some of these functional groups later in Block 1. For now,
just familiarise yourself with the functional groups themselves.


1.1.5 Classification of alcohols (and alkyl halides)

Although all alcohols will display similar reactivity, the outcome of a chemical reaction will
also depend on the carbon to which the –OH is attached.
As a result it is helpful to classify alcohols based on the number of carbons attached to the
C-OH carbon. These are classified as follows:
1° 2° 3°
primary secondary tertiary
OH OH OH
H 3C C H H3C C CH3 H3C C CH3
H H CH3
for one two three carbons bonded to carbon
bonded to oxygen. C-OH
Examples:
OH OH CH3 OH CH3

H C CH2CH3 H3C C CH H3C C CH
H H CH 3 CH3 CH3
1o 2o 3o
We also use this notation for alkyl halides. A modified version of this notation is used for amines.
Practice Question:
Using your knowledge of the bonding arrangements of C, N, O, H and halogens, draw one
plausible structure for each of the following molecular formulae:
CH3Br CH2O C2H4O

1.2 DRAWING CHEMICAL STRUCTURES
1.2.1 Condensed Structures
In the expanded structure, each line represents the two electrons in a bond.
To convert to a condensed structure, ‘get rid’ of the bonds by writing each carbon followed by
what is directly attached.
(a) (b) CH3OH

(c)
1.2.2 Line Structures

The basic principles are:
1. Lines represent bonds (2 bonding electrons)
2. C is the basis of structure so:
a. Carbon atoms not shown – assumed to be at intersections and end of lines.
b. C-H bonds omitted (hydrogen count assumed from valence)
c. All heteroatoms shown, including hydrogens bounded to heteroatoms.
3. Geometry depends on hybridisation – use realistic bond angles.
Examples:
1.2.3 Showing Bonds in 3D

When you want to show the 3D shape of a molecule:
• Bonds in the plane of the paper:
• Bonds coming towards you:
• Bonds going away from you:

Practice Question:
1.
2.
Molecular Formula: ________________
1.3 HYBRIDISATION
1.3. 1 Carbon-carbon bond strength – a conundrum.
Consider the carbon to carbon bond strength on going from a single to double to triple bond.
Bond Enthalpy /kJ mol-1
[single, 2 electrons] C-C (ethane) 348
[double, 4 electrons] C=C (ethene) 614
[triple, 6 electrons] C≡C (ethyne) 839
A double bond is stronger than a single bond, but not twice as strong. The second bond (and
the third) must be weaker than the first!
1.3.2 Hybrid Orbitals

In free atoms, electrons are in atomic orbitals (AOs). Carbon has valence electrons in:
2s orbital 2p orbitals
Covalent bonds form when atomic orbitals overlap to form molecular orbitals.
This overlap can be good (end on)
Bonds formed by end-on overlap of AOs are called σ-bonds.
Side-on overlap of AOs gives π-bonds.

π-Bonds are weaker than σ-bonds.

A single bond is a
A double bond is made from one and one
A triple bond is made from one and two
This is why double bonds are reactive, whereas single bonds are inert.
Methane – a Second Conundrum

Methane (CH4) has 4 single C─H bonds.
AO Theory says these arise from overlap of a hydrogen 1s orbital with either the 2s or 2p
orbitals of carbon. This could be:
1s with 2s or 1s with 2p
However, all four bonds in methane are identical.
We explain this observation in terms of hybridisation.

sp3 hybridisation – alkanes eg methane
2s orbital mixes with all three 2p orbitals
1 × s + 3 x p = 4 × sp3
4 identical orbitals = 4 σ-bonds
tetrahedral
sp2 hybridisation – alkenes
• 2s orbital mixes with two 2p orbitals
• 1 × s + 2 × p = 3 x sp2 + 1 x p (unhybridised)
• 3 identical orbitals, 1 different = 3 σ-bonds, 1 π-bond
e.g. ethene
trigonal planar
sp hybridisation – alkynes
• 2s orbital mixes with one 2p orbital
• 1 x s + 1 x p = 2 x sp + 2 x p (unhybridised)
• 2 identical orbitals, 2 different = 2 σ-bonds, 2 π-bonds
e.g. ethyne
linear
Note that rotation about double and triple bonds would require breaking a π-bond – incurring
a significant energy penalty.

Bonding - Summary
Carbon bonded to: Examples Geometry at Carbon Hybridisation
(bond angle)
four atoms CH4, CH3CH3, CH3X
(single bonds) (X = halogen, OH ....) tetrahedral (109.5 o)
three atoms CH2=CH2, H2C=O

(two single bonds, trigonal planar (120 o)
one double bond)
two atoms HC≡CH, CH3C≡N
(one single bond, linear (180 o)
one triple bond OR O=C=O, CH2=C=CH2
two double bonds)
By looking at the bonding ‘pattern’ around a carbon in any molecule you should be able to give
the notation (sp3, sp2, sp) and state the geometry about that carbon.
Practice Question:
σ-bonds ____________ ____________ ____________

π-bonds ____________ ____________ ____________
hybridisation at * ____________ ____________ ____________
REVISION EXERCISES FOR BLOCK 1 UNIT 1

1. Indicate:
a) The notation (sp3, sp2, sp) for each carbon atom in the following molecules.
b) The position of π-bonds.
O
CH2CH=CHCH=CH2 H3C OH
C CH
H3C CH3
O
CH3
C O
(CH3)2C CH CH3O
2. State the bond angles about each carbon atom in the molecule CH2=CHCH2C≡CH.
Draw as a line structure.
3. Give the molecular formulae for the compounds shown below.

O CH3
O
O CH2
CH2OH
O CH2CH3

UNIT 2 - ISOMERISM
Pre-Lecture Reading - Lecture 3
2.1 CONSTITUTIONAL ISOMERS
Isomers are simply compounds that have the same molecular formula, but differ in some
way in their arrangement in space. There are several different types of isomers, and we will
look at each of these over the next few lectures.
Consitutional Isomers: have the same molecular formula, different atom-to-atom bonding
sequence.
e.g. C4H10O
The number of constitutional isomers increases sharply with size.

Molecular Number of Molecular Number of
Formula Constitutional Isomers Formula Constitutional Isomers
75
C4H10 2 C10H22
366,316
C6H14 5 C20H42
>62 trillion
C7H16 9 C40H82
2.1.1 Drawing Constitutional Isomers Systematically

The molecular formula can tell us important information.
• For CnH2n+2 the molecule is said to be fully saturated, meaning it only contains single (σ)
bonds and no rings.
• For CnH2n the molecule must contain either one double bond or one ring.
or
Example: C3H6
The number of rings or π-bonds (called double bond equivalents, or DBEs) can be calculated
from the molecular formula.
Double bond equivalents (DBEs) = ½ (2n4 + n3 - n1 + 2)
n is the number of atoms with the subscripted valence.

In practice (in this course): n4 = carbon; n3 = nitrogen and n1 = hydrogen or halogens. Oxygen
doe not appear in the DBE formula.
Using the molecular formula and the calculated double bond equivalents (which will
represent either a pi-bond or a ring) the potential functional groups can be determined.

How to draw constitutional isomers systematically.
Using the molecular formula, calculate the number of DBEs.
Example: C4H8O DBEs = ½ (8 + 0 – 8 + 2) = 1
Molecular Formula Composition
DBEs C, H C, H, one O C, H, two O C, H, N
0 alkane alcohol, ether amine
1 alkene, aldehyde, carboxylic acid, (imine)

cycloalkane ketone ester
2 alkyne (nitrile)
Select functional group(s) to account for DBE(s)

Add functional groups from the DBE = 0 category if necessary to account for all the heteroatoms
in the molecular formula.
Possible functional groups accounting for C4H8O:
(a) aldehyde or ketone (1 DBE, 1 oxygen)
(b) alkene (1 DBE) + alcohol or ether (1 oxygen)
(c) cycloalkane (1 DBE) + alcohol or ether (1 oxygen)
For each functional group IN TURN start with the straight chain isomer and work from there.
Tips: Work through each functional group systematically. Within each category, change
one dimension at a time. Where a ring is incorporated in the structure, reduce the ring size
systematically and for each ring size explore the substituent position(s) around the ring
logically. The possibility of incorporating the functional group into the ring must also be
considered and worked through.
So for C4H8O:
aldehyde or ketone cycloalkane + alcohol or ether

OH
O O O OH OH HO CH3
H H
CH3
alkene + alcohol or ether* cycloether
OH
OH O O O O
OH
HO
CH3 H3C CH2CH3
OH
OH O O
CH3
O CH3 H 3C CH3
OH
OH
O O
O
* some of these are unlikely to exist. This is covered extensively at second year.

Practice Question: Calculate the number of DBEs for the molecular formula C5H7Br. List
all possible functional groups or combinations of functional groups consistent with the
molecular formula and give one example of each.
Want more practice with these concepts? Try BestChoice modules:

- Block 1 – Structure A and Structure B
- Block 1 – DBEs
2.2 CONFORMATIONAL ISOMERS

Same molecular formula, same atom-to-atom bonding sequence but the arrangement in
space differs. Can interconvert by rotation about a single bond.
No bond breaking is required for interconversion and most conformational isomers intercon-
vert readily at room temperature. From a chemical perspective, conformational isomers are
the same compound.
The conformation of a molecule (called a conformer) is a particular shape it adopts as a result
of rotation about bonds.
2.2.1 Drawing Conformers

Conformers need to be drawn so as to show the 3D spacial arrangement of atoms. There are
two commonly used representations. The sawhorse projection and the Newman projection.
Example: CH3CH3
“Sawhorse” projection
most stable conformation least stable conformation
rotate by 60o

Newman Projection: viewed along the C-C bond. The circle represents the rear carbon.
Bonds to the rear carbon drawn to the edge of the circle.
Example: Butane (CH3CH2CH2CH3).
Viewed along the C2-C3 there are two possible staggered and two possible eclipsed
conformations.
CH3 CH3 CH3 CH3
H H H H
H H H H
staggered eclipsed staggered eclipsed
repulsions minimised largest groups not largest groups

greatest distance eclipsed
apart
Practice Question: Draw the Newman projection (viewed along the C1-C2 bond) for the anti
conformer of

2.2.2 Cyclohexane Conformers
Bond angles 109o - not flat!
As with butane conformers, there are an infinite number of potential conformers for cyclohexane,
but we are only concerned with the extremes - the chair conformer and the boat conformer.
In chair conformers, we can distinguish two distinct sets of

hydrogens, which alternate above and below the ring.
Whereas for the boat conformer, no formal designation of axial and

equatorial is possible. H H
H
H H
We can compare the relative energies of the two conformations H by
consideration of their Newman projections. H H
H H
H H
4 H H 3 6 HH CH2 HH
5 6 H CH2 H CH2
4 5
H CH2 H
3
2
H H 2 1
HH HH
1
Lowest energy conformation =
Rotation of bonds gives a second chair conformer. Consider the axial bonds in chair A:
A B
On converting from Chair A to Chair B (called a ‘ring flip’):

All axial groups become:
All equatorial groups become:

Drawing chair conformers (in three simple steps):
1. 2. 3.
Draw two parallel lines, Place topmost carbon above

Place the bottommost carbon
slanting downwards and and to the right. Connect the
below and to the left. Connect
slightly offset. bonds. the bonds.
Note that bonds to the bottommost carbon should be parallel to bonds to the topmost carbon.
To draw the other chair conformer:

1. 2. 3.
... slanting upwards... ... above to the left... ...below to the right...
2.2.3 Substituted Cyclohexanes

Consider methylcyclohexane:
Unfavourable interactions No such unfavourable

between -CH3 at C-1 and interactions.
the -H at C-3/C-5.
In general the favoured conformer for substituted cyclohexanes has the largest atom(s)/
group(s) in the
It is not always possible to have ALL substituents equatorial.

For example: consider the following disubstituted cyclohexane: Br Cl

2.3 Configurational Isomers
Same molecular formula, same atom to atom bonding sequence but the arrangement in
space differs. Can only be converted by breaking and reforming a covalent bond.
There are two classes of configurational isomers.
- Enantiomers – non-superimposable mirror images.
- Diastereomers – everything else.
We will cover E/Z and cis/trans diastereomers first, but as you will see, these are not the only
types of diastereomers.
2.3.1 cis / trans isomers – cyclic compounds

Although most single bonds rotate freely, in rings rotation cannot realistically occur.
Substituents on the sp3 carbons of a ring can be either above or below the plane of the ring and
are fixed in this position. The terms cis and trans are used to describe the relative positions
of substituents on a ring. The cis and trans isomers of compound are configurational isomers.

It is important to note that cis and trans are relative terms. They explain where one substituent
is in relation to the other substituent, however they do not describe absolute stereochemistry.
2.3.2 E / Z isomers – alkenes

The presence of a π-bond also fixes atoms in space as there is no free rotation about π-bonds.
As a result, two configurations are possible.
≠
Rotation would require
breaking the π-bond.
E/Z isomers exist for alkenes where the following holds true:
W Y
C C W ≠ X and Y≠Z
X Z
If w = x or y = z (for example, both Y and Z are hydrogen below) then:

Br H H 3C H
C C = C C
H 3C H Br H

Practice Question: Identify the type of isomerism for each pair of cyclobutanes. Where
appropriate, assign as cis or trans.

- Block 1 – cycloalkane stereochemistry
The Cahn-Ingold-Prelog Rules (CIP Rules)

The sequence rules for assigning the configuration as E or Z were developed by Cahn, Ingold
and Prelog and hence often are known as the CIP rules.
STEP 1: Looking at each sp2 hybridised carbon in turn determine the relative priority (Hi/Lo)
of the two groups attached by single bonds as follows:
(a) Considering the two atoms attached directly to the sp2 carbon, the higher the atomic
number the higher the priority.
H < C < N < O < F < Cl < Br < I
(b) If the two directly attached atoms are the same, go one step out until the first
point of difference is assigned.
Example: -CH3 versus -CH2CH3
Ethyl has the higher priority C>H
Example: -CH(CH3)2 versus -CH2CH3
2-Propyl has the higher priority C, C > C, H

(c) If the group attached contains a double bond, treat it as two single bonds to the same
element.
Example: -CHO versus -CH2OH

STEP 2: Having assigned the priorities for the substituents on each sp carbon of the double
2
bond:
If the two higher priority groups are on the same side of the double bond
the alkene has the Z configuration (from the German zusammen: together). C C
If the two higher priority groups are on opposite sides of the double bond
the alkene has the E-configuration (from the German entgegen: opposite).
C C
Worked example:
Cl F
C C
H CH 2CH3
H 3C CH=CH 2
C C
H CO 2H
Practice Question: Classify each of the following as either E or Z.

(a) (b)
Give the formal name for (a) including the stereochemical descriptor.

2.3.3 Enantiomers
Enantiomers are non-superimposable mirror images.
Enantiomers can exist when you have and sp3 carbon with 4 different groups attached.
Such a molecule cannot be superimposed

on its mirror image.
The molecule is said to contain a stereogenic centre (C*) and the molecule is chiral.
Example: 2-chlorobutane
*Indicates a stereogenic centre (an asymmetric carbon).
Where an sp3 carbon has two identical atoms or groups attached,

there is a plane of symmetry and the molecule is superimposable
on its mirror image.
Such a molecule is said to be
Practice Question: Identify any stereogenic centres in the following molecules.
Pre-Reading Lecture 5: To keep your notes easy to follow for study purposes, the pre-
reading for this lecture is on page 25. It is still expected that you complete the pre-reading
prior to the lecture.

A pair of enantiomers will have identical physical (eg melting point) and spectroscopic
properties. However, enantiomers differ in their interaction with a chiral medium or chiral
reagent, for example, plane polarised light.
Schematic representation of a polarimeter:
Because an enantiomer interacts with plane polarized light, the compound is said to be optically
active, and the amount of rotation (α) is characteristic of the enantiomer.
One enantiomer causes clockwise rotation of light - labelled (+) or

The other enantiomer causes anticlockwise rotation - labelled (-) or l
The magnitute of the rotation is the same for both enantiomers (e.g. +15o and -15o).
The sign (+/-) must be determined experimentally and does not tell us about the absolute
configuration of the atoms/groups about the stereogenic centre.
A mixture of equal amounts of the two enantiomers is called a racemic mixture. A racemic
mixture will rotate light equally in both directions, and thus show an overall rotation of zero.
Determining absolute stereochemistry – R / S notation

As with E/Z double bonds, we need to communicate the configuration at a stereogenic carbon
in an unambiguous way.
(a) The four groups attached to C* are ranked from highest (1) to lowest (4) priority using
the CIP rules.
(b) Orient the molecule so that the lowest priority group (4) is pointing away from you.
(c) Observe the decreasing order of priority of the remaining substituents (1-3).
If the three higher ranked substituents have

descending order of priority in a clockwise
direction, we say the stereogenic centre has the R
configuration.
However, if the descending order of priority of
the three higher ranked substituents is in an
anticlockwise direction, the stereogenic centre
has the S configuration.

e.g.

Practice Question: For the following compounds, rank the groups from highest (1) to lowest
(4) priority according to the CIP rules, and then assign the configuration of the stereocentre.

- Block 1 – enantiomers
Enantiomers in Nature
As you saw in the pre-reading, enantiomers differ in their interaction with plane polarized
light. In fact they interact differently with all chiral environments, including enzymes and other
chiral molecules. As a result, enantiomers are prevalent in nature. Biological systems tend to
produce chiral compounds as single enantiomers. In the laboratory, this is much harder to
achieve, as you will see in Block 4 and Block 6 this semester.
2.3.4 Diastereomers (again)

Diastereomers are configurational isomers that do not have a mirror image
relationship.
We have already seen cis/trans diastereomers (rings) and E/Z diastereomers (alkenes).
Diastereomers can also occur where we have multiple stereocentres in the same molecule.
Consider the following 3D representations of 2,3-difluorobutane.
(a) and (b) are ____________________. (c) and (d) are _____________________.
(a) and (c) are _______________________. Stereoisomers - but not mirror image forms.

2.4 Isomers – A Summary
Looking at isomers of dimethylcyclohexane:
H 3C CH3 CH3 CH3 CH3
These are all constitutional isomers. CH3
CH3
Each of 2, 3 and 4 can exhibit CH3
configurational stereoisomers. 1 2 3 4
For example, 1,2-dimethylcyclohexane (2): CH3 CH3

CH3 CH3
1,2-cis 1,2-trans
Both can exist as two chair conformers.
(ax)
cis-1,2-dimethylcyclohexane CH3 (ax)
A 1 CH3 B
H (eq)
CH3 (eq) 2 CH3
2 H 1
H H
Both A and B have one group methyl group axial and one methyl group equatorial. They are
thus equally stable.
trans-1,2-dimethylcyclohexane CH3 (ax)

A 1 H B
H (eq)
H 2 CH3
2 (eq) H 3C 1
CH3 (ax) H
Here, B has the two methyl groups equatorial, which is more stable (and thus more
favourable) than conformer A, which has both methyl groups axial.
Whereas the cis isomer contains a plane of symmetry, the trans isomer does not and can exist
as enantiomers.
plane of symmetry
H 3C CH3 H CH3 H 3C H
H H H 3C H H CH3
cis trans

1. Which of the following are constitutional isomers?
O CH3
O
O CH2
CH2OH
O CH2CH3

2. Draw the line structure or condensed structural formulae for each of the following:
(a) Four constitutional isomers of the molecular formula C4H9Br.
(b) Compounds with the formula C5H10O containing a carbonyl group (7 total).
(c) Carboxylic acids and esters with the molecular formula C4H8O2 (6 total).
(d) Four isomers of the molecular formula C3H9N.
3. For the molecular formula C4H8O2 draw a(n)
(a) carboxylic acid (b) alcohol-aldehyde (c) alcohol-ketone
(d) aldehyde-ether (e) ether-ketone (f) alkene-dialcohol
(g) alkene-diether (h) cyclic dialcohol
4. Using Newman projections for 1-bromopropane, viewed along the C-1 C-2 bond, draw
six conformational isomers which differ by rotation of 60°.
Label the most and the least stable conformers, as well as those conformers which
would be designated as gauche and anti.
5. Draw a chair conformer for a disubstituted cyclohexane, molecular formula C9H18, in
which one of the alkyl substituents is axial and the other is equatorial.
6. Draw the two chair conformers, indicating which is more stable, for each of:
(a) ethylcyclohexane (b) trans-1-ethyl-4-methylcyclohexane
7. Assign the configuration of the following compounds as E/Z or cis/trans as
appropriate. O
CH2Br Cl
H 3C Br CH3CH2 OCH3 H 3C CCH3 CH=CH2
C C C C C C
H CH2CH3 H CH3 H CO2H H H H
H
Br
8. For the compound C5H9Br

(a) Calculate the double bond equivalents.
(b) Give the structure of a ‘straight chain’ (non-branched) constitutional isomer
which can exist as E/Z isomers.
(c) Give the structure of a ‘straight chain’ constitutional isomer which cannot exist
as E/Z isomers.
(d) Give the structure of a cyclic compound which can exist as cis/trans isomers.
9. Establish whether the following have the R- or S-configuration.
(a) OH (b) CH2Cl (c) CH2CH3 (d) CH2CH3 (e) H
H3C H H3C
H CH3 H3C CHCH3 H3C Br F
Cl Br H CHO
CH3 NH2
10. Draw three dimensional representations of the R and S enantiomers of:
(a) (b) Br (c) OH (d) CHO

=
CH3CHBrCl ClCH2CHCH2CH3 CH3CHCO2H CH2 CHC(CH3)CH2Cl

UNIT 3 - NOMENCLATURE
3.1 THE BASICS - ALKANES
CnH2n+2 Simple Alkane Attached to something
CH4 methane methyl
ethane ethyl
propane propyl
butane butyl
pentane etc
hexane
heptane
octane stemane
nonane
decane
General rules (for alkanes and alkyl halides):

(a) Find the longest unbroken chain of C atoms – this gives the stem (parent chain).
3
9 carbons - nonane
6
(b) Identify the substituents (atoms/groups other than H) attached to the parent chain.
These have been circled on the structure above. Number the chain to give the lowest
possible (sum of) number(s) for the substituents.
In the above example, numbering from left to right puts branches at carbons 3 and 6,
whereas numbering right to left puts branches on carbons 4 and 7.
3+6=9 < 4 + 7 = 11
So in this case, you would number from left to right.
(c) Name each substituent, indicating attachment position (use hyphen).
6-ethyl
3-methyl
(d) Arrange substituents alphabetically, separating numbers from letters with hyphens and
leaving NO SPACES.
6-ethyl-3-methylnonane

Other substituents you should be familiar with are:
Alkoxy substituents (-OR) – stem of R + oxy.
e.g. CH3O- methoxy
Halogens – delete ine and add O.
e.g. Br- bromo
(e) If a substituent can be attached in more than one way, number the attachment point on
the substituent too.
CH3CH2CH2- (CH3)2CH-
propyl (1-propyl) 2-propyl (isopropyl)
(f) If there is more than one of a particular substituent use prefix di, tri, tetra etc
ethyl
methyl 6-carbon backbone = hexane
methyl 2 x methyl at carbon 2 AND
1 x methyl at carbon 3 = 2,2,3-trimethyl
methyl 1 x ethyl at carbon 4 = 4-ethyl
4-ethyl-2,2,3-trimethylhexane
(g) For cycloalkanes, add ‘cyclo’ to the alkane name.
e.g. cycloapentane
3.2 NAMING FUNCTIONAL GROUPS

3.2.1 One Functional Group
(a) Identify the functional group present.
(b) Identify the longest unbroken chain that contains that functional group.
(c) Number the chain to give the functional group the lowest possible number.
Note: If a functional group is always at the end of a chain (eg acyl halide) the functional group
is always considered to be at carbon 1 and so the number ‘1’ is not included in the name.
(d) Add appropriate suffix to denote functional group.
2
alkene (ene) acyl chloride (oyl chloride)

5 carbon chain (pent) 2-carbon chain (ethan)
functional group starts at C-2 functional group on C-1
pent-2-ene ethanoyl chloride
(e) Add substituents if required.

methyl

alcohol (ol) carboxylic acid (oic acid) ester (yl oate)
3-methylpentan-2-ol 2-chlorobutanoic acid methyl ethanoate

3.2.2 When more than one functional group is present
We will only cover the case where there is one oxygen-containing functional group and one or
more C-C double/triple bonds.
(a) Name based on the oxygen containing functional group.
(pentan-2-one)
pent-3-en-2-one
2 3
(b) Replace the ‘a’ of the alkane stem with -#-e where # describes the position of the C-C
multiple bond.
3.3 NON-SYSTEMATIC NAMES

You will NOT be examined on non-systematic names. However, you are likely to encounter
many of these terms in your future studies. Some non-systematic names for compounds com-
monly used in organic chemistry, biology and medicine are given below.
Hydrocarbons: CH2=CH2 CH2=C=CH2 HC≡CH

ethylene allene acetylene
Halogen containing compounds: CHCl3 CCl4 CH2=CHCl
chloroform carbon tetrachloride vinyl chloride
Alcohols: (CH3)3COH t- or tert-butyl alcohol HOCH2CH2OH ethylene glycol
Aldehydes: HCHO formaldehyde CH3CHO acetaldehyde
Ketones: acetone
Acids: HCO2H formic acid CH3CO2H acetic acid

Esters: CH3CO2CH3 methyl acetate CH3CO2CH2CH3 ethyl acetate
Practice Question:
1. Give the systematic names for the following molecules.
2. Draw the structure of 2,3-dimethylhex-2-ene.

- Block 1 – Naming Alkanes
- Block 1 – Nomenclature

1. Draw structures for the following compounds.
a) 2,2,4-trimethylpentane h) ethyl butanoate
b) 3-methylpentan-2-one i) butanoic acid
c) 5-ethyloct-3-yne j) propanoyl chloride
d) 5-methylhexan-2-ol k) 3-methylpentanamide
e) 3-methylcyclopentanol l) bromobenzene
f) 2,5-dimethylhexanal
g) 2-chlorobuta-1,3-diene

UNIT 4 - MECHANISM and REACTIVITY

4.1 ELECTRONEGATIVITY AND BOND POLARITY
Although most bonds in organic molecules are classed as covalent, they range in character from
strictly covalent (C–C, C–H) to polar bonds such as O–H where electrons are not shared equally
between bonded atoms. One measure of bond polarity is the difference in electronegativity
between the bonded atoms.
Electronegativity (en): a measure of ability of a bonded atom to attract electrons to itself. As

the difference in electronegativities [Δ(en)] of the bonded atoms increases the polarity of the
bond increases. The more electronegative element of the bond has partial negative charge (δ-);
the less electronegative one has partial positive charge (δ+).
From this we can predict C–C (Δ(en) = 0) bonds to be non-polar, and C─O (Δ(en) = 1) or C─Cl
(Δ(en) = 0.5) to be polar.
Double bonds are more readily
polarised due to the relative
mobility of π-electrons. As a result,
a C=O bond is more polar than a
C─O bond.
Ionic bonds, such as those found
in amine salts and carboxylic acid
salts are even more polar than
covalent bonds.

4.2 INTERMOLECULAR FORCES

Intermolecular forces are non-bonding electrostatic interactions between molecules (or
atoms, or ions). They are weaker than bonding interactions, and are responsible for many of
the physical properties of compounds, such as boiling point and solubility. Three classes of
intermolecular forces are particularly relevant to organic molecules: temporary dipole-dipole
interactions, dipole-dipole interactions and hydrogen bonding.
4.2.1 Momentary dipole-dipole interactions

Although the cloud of electrons surrounding a molecule may, on average be symmetrical,
electrons are mobile, at a given moment will not be evenly distributed. This uneven electron
distribution gives rise to a temporary dipole, where one side of the molecule has a temporary
excess of electrons and a partial negative charge (δ-). The other side of the molecule will have a
temporary deficit of electrons and a partial positive charge (δ+). In essence, a miniature magnet
is formed. This dipole can cause distortions in neighbouring electron clouds, leading to attractive
electrostatic interactions between molecules. These interactions are called temporary dipole-
dipole interactions, or dispersion forces. The larger and more polarisable (distortable) the
electron cloud on a molecule, the stronger the momentary dipole-dipole interactions will be.
As a result, these forces increase with molecular size.
Although momentary dipole-dipole
interactions are weak in comparison
to bonding interactions, they are the
dominant interaction between molecules.
Uneven distribution Momentary Induced dipole in
of electrons dipole neighbouring atom
4.2.2 Dipole-dipole interactions

The electron cloud around a non-polar molecule like methane is symmetrical. However this is not
true of all organic molecules. Where a molecule contains atoms of differing electronegativities,
the electron cloud will not be symmetrical, as the electrons in a given bond will spend (on
average) more time with the more electronegative atom. We say that such a bond is polar.
A polar bond is a permanent dipole. Molecules containing polar bonds may themselves have
an overall dipole – that is a permanently uneven distribution of electrons. The electrostatic
interactions between molecules with permanent dipoles are called dipole-dipole interactions.
The strength of the dipole-dipole interaction will increase with the overall polarity of the
molecule. This will be a function of both the polarity of the individual bonds and the shape of
the molecule.

4.2.3 Hydrogen Bonding

Hydrogen bonding is a special case of dipole-dipole interaction. O─H, F─H and N─H bonds are
very polar. The dipole-dipole interaction between a δ+ H and the δ- O (or F/N) of an adjacent
molecule is particularly strong.
R
R
O R
H δO
-
H Oδ-
δ+ H
δ+
This type for interaction is called a hydrogen bond (H- bond).

Without H-bonds our proteins would not fold, water would be a gas, ice would sink and life on
earth would not be possible.
Practice Question. Identify any polar bonds in the molecules below. List the types of
intermolecular interactions possible for each compound. Rank them from strongest to weakest
for each of the following types of interactions:
1. momentary dipole-dipole interactions
2. dipole interactions.
pentane butanal butanol
O
CH3CH2CH2CH2CH3 CH3CH2CH2CH CH3CH2CH2CH2OH

- Block 1 – Polarity
- Block 1 – Intermolecular Forces

4.3 PHYSICAL PROPERTIES OF ORGANIC MOLECULES
4.3.1 Boiling Point and Intermolecular Forces
The boiling point of a compound is related to:
(a) molecular size
CH4 −161 °C Increases with molecular size due
CH3CH3 −89 °C to increasing momentary dipole-
CH3CH2CH3 −42 °C dipole interactions.
CH3CH2CH2CH3 −0.5 °C
(b) molecular shape
(CH3)4C 9 °C Minimal contact.
CH3

CH3CHCH2CH3
28 °C
Good contact.
CH3CH2CH2CH2CH3 36 °C
Intermolecular forces are strongest when molecules are in close proximity, so decreased
‘branching’ correlates with increases b.p. as molecules can stack closer together.
(c) presence of polar bonds For compounds with similar molecular

CH3CH2CH3 −42 °C weights, more polar functional groups
CH3OCH3 −24 °C correlates with higher b.p. This can
CH3CHO 65 °C be explained in terms of increasing
CH3CH2OH 78 °C dipole-dipole interactions.
However, for molecules of different size, it is the difference in the momentary dipole-dipole
interactions that has the greatest effect on boiling point.
4.3.2 Polarity and Bioavailability

Bond polarity is an important factor in predicting reactivity of molecules. It is also an important
factor influencing the (bulk) physical properties on the compound. The overall polarity of a
molecule is a function of both the size of the hydrocarbon (non-polar) portion and the nature
of any polar groups.
Overall polarity affects solubility.
Balancing solubility properties is particularly important when designing drugs targeting

the central nervous system. They must be hydrophilic enough to enter the blood stream but
lipophilic enough to cross the blood-brain barrier.

4.3.3 Chromatography
Differences in polarity can be exploited to separate materials in the laboratory (Lab Assignment
1). Standard chromatography uses a polar stationary phase, onto which the mixture of interest
is adsorbed. A suitably polar mobile phase (solvent) is passed over the stationary phase, moving
the components of the mixture along.
Polar solutes are more attracted to the polar stationary phase and move slowly.
Whereas, non-polar solutes are less attracted to the polar surface of stationary phase and
therefore move more rapidly.
Practice Question. Looking back at the molecules from the practice question this morning:
1. Which one will have the highest boiling point? Explain.
2. Which one will move the fastest on a chromatography column? Explain.
pentane butanal butanol
O
CH3CH2CH2CH2CH3 CH3CH2CH2CH CH3CH2CH2CH2OH

4.4 Electron Movement in Organic Reactions
4.4.1 An Introduction to ‘Curly Arrows’
During the course of a chemical reaction bonds are broken and new bonds formed. ‘Curly
arrows’ are a short hand notation to describe the movement of bonding electrons during
reactions.
Electrons ‘start’ at the tail of the arrow and move
towards the direction of the head of the arrow.
4.4.2 Breaking covalent bonds

A covalent bond can cleave in two possible ways with respect to the electrons in the bond.
(i) or (ii)
In homolytic bond cleavage, one electron from the bond ends up on each of the atoms which
were formerly bonded.
A—B
The movement of each single electron is symbolised by a single-headed curly arrow (a
“fishhook”). The species generated are radicals (neutral species with an unpaired electron).
In heterolytic bond cleavage, both electrons from the bond end up on one of the atoms which
were formerly bonded.
A—B
The electron movement is shown by a two-headed curly arrow, symbolising the movement of
two electrons (an electron pair).
The direction of electron pair movement depends on the relative electronegativities of the
two atoms involved in the bond. Electrons will move towards the more electronegative atom
of the bond (in this case, B).
Note the change in formal charge on going from reactants to products.

• A loses ‘ownership’ over one of the (previously) shared electrons and becomes one
unit of charge more
• B gains ‘ownership’ over one of the (previously) shared electrons and becomes one
unit of charge more
Example: (a) (CH3)3C A
(b) (CH3)3C A
(c) (CH3)3C A
If A is more electronegative than carbon, bonds will break as in (a). e.g.

If A is less electronegative than carbon, bonds will break as in (b). e.g.

4.4.3 Carbocations
As carbon is not very electronegative (lecture 1) carbocations are more common than
carbanions. Like alcohols and alkyl halides they are designated:
1° 2° 3° for
alkyl/aryl groups attached to C+.
The relative stability is:
eg (CH3)3C+ > (CH3)2CH+ > CH3CH2+ > CH3+
The geometry of carbocations is planar (sp2 hybridised).
4.4.4 Forming Covalent Bonds

Bond forming is the reverse of bond breaking.
Note again the change in formal charge going from reactants to products. In a covalent bond,
each atom officially ‘owns’ one of the two electrons in the bond. In the first two examples above,
the anion donates two electrons into the new bond, but now ‘owns’ only one and becomes one
unit of charge less negative (the reverse is true for the cation).
Practice Question: By following the electron movement, draw the products of the following
reactions.
Challenge Question: Use curly arrow notation to show electron movement in the following
reaction.

Polar and Non-Polar Reactions
4.4.5 Non-polar reactions
These are typified by the reactions of free radicals.
eg
CH3 + Cl H 3C Cl
Bond breaking and bond making steps may take place at the same time.
Cl + H CH3 Cl H + CH3
4.4.6 Polar reactions

Most of the reactions we will see in this course involve one bonding partner supplying the
electron pair and the other receiving it (to form a new bond).
The electron donor is called the nucleophile (nucleus lover). Nucleophiles are electron-
rich. They can be neutral or negatively charged and will have either lone pairs of electrons or
electrons in π-bonds.
neutral, lone pairs negatively charged (lone pairs)
NH 3 NH 2R HOR H 2O HO RO H X NC
δ- δ+
C C C C RMgBr δ+C O δ-
π-electrons -ve atom of a polar bond (lone pairs)

The electron acceptor is called the electrophile (electron lover). Electrophiles are electron
deficient. They can be neutral or positively charged.
positively charged +ve atom of a polar bond
δ+
H H 3O X NO 2 R 3C C Cl δ- δ+C O δ-
A polar reaction occurs when a nucleophile reacts with an electrophile to form a new covalent
bond.
H OH H OH
H NH 3 H NH 3
H H 2C CH 2 H 3C CH 2
(CH 3) 3C H 2O (H 3C)3C OH 2

Practice Question: Determine whether the following are more likely to react as electro-
philes, nucleophiles or both.

- Block 1 – Nucleophiles and Electrophiles
4.5 Reaction Classification

By studying the ‘types’ of reactions that can occur, we can easily predict the outcome of chem-
ical reactions. You will see three classes of reactions in this course:
Useful sub-classifications include:

• Polar/non-polar (radical)
• Involving nucleophilic / electrophilic reagent
• Nature of substrate (alkyl, aryl, acyl)
4.5.1 Substitution
In a substitution reaction one atom or group is replaced by another through the breaking and
formation of σ-bonds. [DBEs remain the same.]
Specific examples:
4.2.2 Addition
In an addition reaction a π-bond breaks and is replace by two new σ-bonds. [DBEs decrease.
Products “less unsaturated”.]
Specific examples:

4.5.3 Elimination
In an elimination reaction two σ-bonds break and a new π-bond forms. [DBEs increase. Prod-
ucts “more unsaturated”.]
Specific examples:
4.5.4 Reaction Classification Summary

Reaction Type Bonds Broken Bonds Formed
Substitution
Addition
Elimination
Practice Question: Classify the following reactions.
Challenge Question:
Classify the reaction above, and use the general scheme to determine the products of the
following reactions:

4.6 Introduction to Mechanism
The detailed pathway by which reactants are converted to products is known as the reaction
mechanism. Often a reaction will take place in multiple steps (elementary reactions) that
occur sequentially. Some species involved in the mechanism (e.g. a carbocation) may be
unstable and short-lived. These are called reactive intermediates..
You will see several mechanisms later in the course, but we are going to start with three here.
4.6.1 Nucleophilic Substitution – SN1 and SN2

From our reaction classification we already know two things: the reaction will involve breaking
and forming a σ-bond, and the reagent will be a nucleophile.
The key difference?
- SN1 reactions occur (bond breaking then bond forming)
- SN2 reactions occur (bond breaking/forming is simultaneous)
The SN2 Mechanism – Bromomethane and –OH

In this reaction carbon−oxygen bond formation and carbon−halogen bond breaking occur
simultaneously in a single step.
The nucleophile is
The electrophile is
Note that the charge on the carbon (initially neutral) does not change on going to products.
This is always the case when there is no change in the number of bonds to a particular atom.
The SN1 Mechanism – Hydrolysis of methylpropane

For the reaction: (CH3)3CBr + H2O → (CH3)3COH + H+ + Br−
Reaction mechanism:
Step 1
Heterolytic bond breaking,
forming a reactive
carbocation intermediate.
Step 2
Polar bond formation with
(CH3)3C+ as electrophile
and H2O as nucleophile.
Step 3
Heterolytic
bond breaking to give a neutral
product.

4.6.2 Drawing Plausible Mechanisms
Taking an example from the previous section, let’s look at a nucleophilic addition using a
strong (charged) nucleophile.
Mechanism:
Y
R
C O
R

1. Categorise the reactions (a) – (f) as substitution, elimination or addition.
NO2
(a) CH4 + Cl2 CH3Cl + HCl
(e) + HNO + H O
(b) (CH3)2C CH2 + H2O (CH3)3COH
3 2
catalyst
(c) CH3C CH + H2 CH3CH=CH2 OH
(f ) CH3CHO + HCN
CH3CHCN
(d) ClCH2CH2Cl + Zn CH2=CH2 + ZnCl2
2. Give the possible products of

(a) heterolysis of the carbon−A bond in (CH3)2CHA.
(b) homolysis of the carbon−chlorine bond in CH3Cl
3. Arrange the carbocations, which would be formed by heterolytic cleavage of the
carbon halogen bond in the following compounds, in order of decreasing stability.
CH3 CH3
(a) CH3CH2Br (b) CH3CH2CCH3 (c) (CH3)2CHCHCH3 (d) CH3CH2CBr
Cl I CH3
4. Draw the structure(s) of each of the following bond-making/breaking processes.

Where applicable, identify the electrophile and the nucleophile.
(a) (CH3CH2)2CH OH2 (d) H3CC C + CH3 Br
(e) H2C CHCl Cl

(b) (CH3)2C C(CH3)2
H CH3
H3C f
() HO C O
(c) C O OCH3
HO H3C
5. Arrange the following compound in order of increasing boiling point.

CH3
(a) CH3CH2CHCH3 CH3CH2CH2CH2CH3 CH3CCH3
CH3 CH3
(b) HCO2H CH3CH2OH CH3OCH3 CH3CH2NH2
6. Arrange the following compounds in order of decreasing polarity.
CH3CH2CH2OH CH3CH2CH2CH3 CH3COCH3 CH3CO2H CH3CH2OCH3
7. Both propanoic acid and methyl ethanoate have the molecular formula C3H6O2. One
boils at 57 °C, the other at 141 °C. Which compound will have the higher boiling point?
Which compound will be the more water soluble and why?

Block 1 Foundations

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CHEM110/Block 1/Foundations/2020 1

This handout should be brought to all lectures.

Laboratory Day and Time: Bench Number:

© School of Chemical Sciences The University of Auckland

At the end of block 1, you should be able to:

© School of Chemical Sciences The University of Auckland

© School of Chemical Sciences The University of Auckland

Pre-Lecture Reading (Lecture 2)

1.1.2 Bonding Arrangements – The Basics

Nitrogen can also form single, double and triple bonds.

*Valence – number of bonds to an atom in a stable, neutral (uncharged) molecule.

1.1.3 Functional Groups

A functional group is a recognizable arrangement of atoms that is characteristic of a

© School of Chemical Sciences The University of Auckland

2. With only aldehyde alkan al

3. With both carboxylic alkan oic acid

acid alkan oic

─C≡ N nitrile alkane nitrile

F: Containing oxygen acyl halide ♦

G: Containing sulfur thiol alkane thiol

© School of Chemical Sciences The University of Auckland

1.1.5 Classification of alcohols (and alkyl halides)

CH3Br CH2O C2H4O

© School of Chemical Sciences The University of Auckland

1.2.2 Line Structures

1.2.3 Showing Bonds in 3D

© School of Chemical Sciences The University of Auckland

Molecular Formula: ________________

1.3.2 Hybrid Orbitals

Bonds formed by end-on overlap of AOs are called σ-bonds.

Side-on overlap of AOs gives π-bonds.

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Methane – a Second Conundrum

However, all four bonds in methane are identical.

We explain this observation in terms of hybridisation.

© School of Chemical Sciences The University of Auckland

three atoms CH2=CH2, H2C=O

σ-bonds ____________ ____________ ____________

REVISION EXERCISES FOR BLOCK 1 UNIT 1

3. Give the molecular formulae for the compounds shown below.

© School of Chemical Sciences The University of Auckland

The number of constitutional isomers increases sharply with size.

2.1.1 Drawing Constitutional Isomers Systematically

Double bond equivalents (DBEs) = ½ (2n4 + n3 - n1 + 2)

n is the number of atoms with the subscripted valence.

© School of Chemical Sciences The University of Auckland

0 alkane alcohol, ether amine

1 alkene, aldehyde, carboxylic acid, (imine)

Select functional group(s) to account for DBE(s)

aldehyde or ketone cycloalkane + alcohol or ether

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Want more practice with these concepts? Try BestChoice modules:

2.2 CONFORMATIONAL ISOMERS

2.2.1 Drawing Conformers

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Example: Butane (CH3CH2CH2CH3).

CH3 CH3 CH3 CH3

staggered eclipsed staggered eclipsed

repulsions minimised largest groups not largest groups

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Bond angles 109o - not flat!

In chair conformers, we can distinguish two distinct sets of

Whereas for the boat conformer, no formal designation of axial and

σ-bonds