Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Lecture 1
Chemistry: What is it good for?
To understand the properties of all matter
To understand the interactions of materials
To understand biological processes
To develop new drugs (antibiotics, anti-cancer agents...)
To develop new materials (plastics, ceramics...)
The first synthetic chemists (making new molecules)
1828; Wohler prepares urea

1857; Perkin makes mauveine from coal tar

Chemical Bonds and Structure

In addressing the properties of different compounds it is useful to group them
into two classes:

Ionic Compounds
Complete transfer of one or more electrons occurs, creating ions.

Ions are held together (in a lattice) by strong

electrostactic forces

Covalent Compounds
Bonding electrons are shared between atoms
Overlap of electronic orbitals gives rise to bonding orbitals, or
covalent bonds

What

bonds?

are

covalent

Two electrons shared between two atoms

Electronic
Configuration
Describes
the
orbitals
a given element

occupied

by

electrons for

Orbital Theory
The space around a nucleus in which an electron is most likely to be
residing is termed an orbital
What does an orbital look like?
The further from the nucleus, the
higher the energy of the orbital
The shape of an orbital varies with type

Electronic Configuration
Energy levels of orbitals...

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Lecture 2
Formation of covalent bonds
A covalent bond is formed by the sharing between atoms of unpaired
electrons
Unpaired electrons are always in the outer (valence) shell highest
energy occupied orbitals
Two theories used to describe covalent bond formation;
o Valence bond theory
o Molecular orbital theory
Valence bond theory

Overlap of two singly-occupied

orbitals gives a bonding orbital
Bonds formed by head-on
overlap of orbitals are -bonds

Molecular orbital theory

Combination of 2 atomic orbitals

gives 2 molecular orbitals
Additive combination gives bonding
molecular orbital (filled, low energy)
subtractive conbinaition gives antibonding molecular orbital (not filled,
high energy)

Formation of covalent bonds

A covalent bond is formed by the sharing between atoms of unpaired
outer shell electrons

Lewis structures
A simple way of representing covalent bonds is by Lewis structures;
o valence electrons are represented by dots
o a stable molecule exists when an inert gas configuration is
achieved for all atoms (stable octet rule)

methane

methanol

Orbital theory and carbon?

The ground state configuration of carbon contains only two unpaired
electrons
Yet carbon forms four covalent bonds to achieve a stable octet

Carbon:

1s2 2s2
methane,

2p2
CH4

Excited state configuration

ground state

Carbon: 1s2 2s2 2p2

two unpaired valence electrons
valence electrons

excited state

Carbon: 1s2 2s1 2p3

four unpaired

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
Bonding in carbon
But
o Bonding in this state would give 3
equivalent bonds (from the 2p
orbitals) and 1 different bond
(from the 2s orbital).

The 2s, 2px, 2py, &2pz orbitals are

sp3 orbitals

Carbon: 1s2 2s1 2p3

state
excited

How
do
we
account
for
experiments that confirm that all
four bonds in methane are of the
same length and strength?

Hybridisation
hybridised to generate four equivalent

Carbon: 1s2 [2sp3]4

possible bonding state

The four sp3orbitals have a tetrahedral arrangement around the

nucleus
This can be determined mathematically (Schroedinger equation),
and/or can be thought of as the arrangement that places the four
orbitals as far apart as possible (VSEPR theory).

Tetrahedral geometry
Methane, CH4
Ethane, C2H6
Oxygen and nitrogen can also be sp3hybridised;

Representation of molecules
Lewis structure;

confusing even with small molecules

Kekule structure (Structural formula);

covalent bonds represented as lines
o cumbersome for larger molecules

Condensed structural formula;

Line structure;
o C-C bonds
o C-H
o
o
Alkanes

drawn as lines
bonds omitted
non-C,H atoms drawn
only H s not bonded to C shown

e.g.

octane

Structural isomers
Alkanes with four or more carbons can exist as structural isomers
Structural isomers have the same molecular formula, but have different
bond connectivity

Structural isomers may have different physical and chemical properties

C6H14

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
C9H8O4

aspirin
and
acetozone
are
structural isomers with different
chemical properties
it is not possible to derive
molecular structures from their
trivial names systematic names
are required

Nomenclature - the rules

Identify the longest carbon chain (parent chain)

Identify the substituent(s)
Number the longest chain to give the lowest possible numbering for the
substituent(s)
Allocate a number to every substituent
List substituents in alphabetical order
Identical substituents are indicated by prefixes: di (2), tri (3), tetra (4)

Isomers of hexane

2methylpentane

3methylpentane

2,3dimethylbutane

a more complicated example...

4-ethyl-2,2,6,8-tetramethylnonane
not
6-ethyl-2,4,8,8tetramethylnonane
2,2,6,8-tetramethyl-4ethylnonane

Functional groups
Organic molecules may incorporate functional groups
Alcohol
Halide
Carboxylic acid
Amine

OH
F,Cl,Br,I
CO2H
NH2

CH3CH2OH
(ethanol)
CH3I
(iodomethane)
CH3CO2H (ethanoic acid)
CH3CH2NH2 (ethylamine)

Conformational isomers
There is free rotation about a -bondan infinite array of conformations
is possible through rotation
a conformer is one specific conformation of a molecule
different conformers are isomers - they differ by the arrangement of
atoms in space

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
Newman Projection
Conformational isomers are easily
distinguished in a Newman
projection (looking directly down a
carbon-carbon bond)
Staggered vs Eclipsed
Staggered conformers are more
stable (lower in energy) than
eclipsed conformers, due to
reduces steric interactions

Lecture 3
Conformers of butane

Conformation
of
longchain alkanes
The most stable conformer of long-chain alkanes is when all antistaggered conformations are adopted, leading to a characteristic zigzag or sawtooth structure.

Lipids
Phospholipids are principle components of cell membranes (lipid
bilayer)
Contain long alkane chains that stack together
Polar groups exposed to aqueous environment

Cycloalkanes
Cycloalkanes have a cyclic structure, and general formula CnH2n
Named by including cyclo prefix

10

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
Cyclopropane
Cyclohexane
Cyclopropane is highly strained, 6-membered rings are strain free,
with both unfavourable bond
with all C-C-C angles close to the
angles,
and
unfavourable
optimal 109.5 for tetrahedral
eclipsing interactions
geometry, and an all staggered
arrangement
This is possible by adopting a chair
conformation

Cyclopentane

Cyclohexane

Cyclohexane chair conformation

The chair conformation results in two types of hydrogen
environments; axial
and equatorial

Ring Flipping
Two chair conformations exist which interconvert by ring-flipping
Ring-flipping interchanges axial and equatorial substituents

11

Substituted cyclohexanes
Equatorial substituents result in more
conformation due to decreased steric interactions

Disubstitued cycloalkanes
Rings prevent free rotation around
single bonds
Isomers can exist when two or more
substituents are attached.
The isomers do not interconvert
(would require breaking of C-C
bonds).
These isomers are stereoisomers they differ by the arrangement of
atoms in space
Also
called
cis/trans
isomers,
diastereomers
Cycloalkanes

12

stable

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Lecture 4
Stereochemistry
Tetrahedral carbons with 2 or 3 groups are
identical to their mirror
images
A tetrahedral carbon with 4 different groups is
NOT superimposable on its mirror image
These
non-superimposable
mirror images are therefore
different substances;i.e. they are isomers
Steoeoisomers
Molecules that are non-super
imposable mirror-image are a
subclass
of
stereoisomers
bond connectivity but differ in the
arrangement of atoms in space)
Specifically they are enantiomers

(same

Chirality (handedness)
Molecules that possess non-superimposable mirror images are said to
be chiral (from the Greek cheir ; hand )
How can we determine if a molecule is chiral?
o It must not contain a plane of symmetry
A tetrahedral carbon with 4 different groups has no plane of symmetry;
such a carbon atom represents an asymmetric centre or stereogenic
centre
Terminology
A molecule is chiral if it is not superimposable upon its mirror image
(which is true if it does not contain a plane of symmetry).
The two non-identical mirror image compounds are called enantiomers.
With a few important exceptions, enantiomers have identical physical
and chemical properties.
Molecules with one asymmetric/stereogenic centre (an sp3-hybridised
carbon with four different groups attached) are always chiral and exist
in enantiomeric forms.
An example: lactic acid
Lactic acid posesses one asymmetric centre and therefore two
stereoisomers (enantiomers) exist

Enantiomers

13

The two ways enantimers can

be differentiated;
o Enantiomers differ in the
way
in
which
they
interact with other chiral
molecules
o Enantiomers differ in the
way
in
which
they
interact
with
plane
polarised light

Rotation of plane polarised light

All chiral compounds rotate the plane of polarised light to some extent this is why they are referred to as being optically active.
A sample of one enantiomer rotates the plane of polarised light with
the same magnitude but in the opposite direction to the other
enantiomer.

Absolute stereochemistry
The (+)- and (-)- description of enantiomers is an observable physical
property, but does not give information about the configuration of the
asymmetric centres
The Cahn-Ingold-Prelog rules allow the description of the specific
configuration of asymmetric centres; (R)- and (S)-descriptors

(R)- and (S)- descriptors

An asymmetric centre is described as being of the (R)- or (S)configuration by;
o Ranking the four substituents (priorities 14)
o Determining a clockwise or anticlockwise sequence
o Assigning (R) or (S)
Cahn-Ingold-Prelog rules
Rule 1:
o Prioritise substituents in decreasing order of the atomic number
of the atom directly attaches

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Rule 2:
o If two directly attached atoms are the same,
compare the second atoms in each group
Rule 3:
o Treat multiple bonds as the equivalent
number of single bonds

Rule 4:
o View the molecule so that you are looking down the bond from
carbon to group 4

anticlockwise
(S)-configuration

clockwise
(R)-configuration

Examples of assigning (R)- and (S)-

4 pointing away
1-2-3 anticlockwise
(S)-configuration

(S)
lactic acid

4 pointing away
1-2-3 clockwise
(R)-configuration

(R)
glyceraldehy
de

15

Lecture 5
The Thumb Rule

Assigning (R)- and (S) If the lowest priority substituent is pointing out of the page:
Rotate the molecule so that it is pointing into the page, then apply
the rules as normal
Reverse the anticlockwise/clockwise rule
Use the thumb rule
More Terminology
An equal misture of enantiomers is termed a racemic mixture
It can be difficult to separate enantiomers from a racemic mixutre as
they have the same physical and chemical properties (m.p., b.p.,
solubility, reactivity)

Chiral Drugs

Only the (S)-enantiomer of dopa is converted to dopamine

A dangerous build-up of the (R)-enantiomer occurs if the racemic drug
is given

Sedative / anti-nausea

16

teratogen:

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
used in late1950s/early
60s to treat morningsickness

causes
birth
defects
(stunted growth of fetal
limbs)

Lecture 6
More than one asymmetric centre
Each asymmetric centre has two possible configurations (R or S)
A molecule with n asymmetric centres has (a maximum of) 2n
stereoisomers

what is the relationship between these molecules?

(stereoisomers that are not enantiomers)
Diastereomers
All asymmetric centres of opposite configuration
enantiomers
At least one asymmetric centre of the same configuration, at least one
opposite
diastereomers

17

Alkenes
Alkenes have the general formula CnH2n
Geometry
Contains C=C bond
Planar arrangement of atoms
Geometry of carbons is trional planar
C=C bond length 1.33 (c.f. 1.54
C=C bond strength 640 kJ.mol-1

for C-C)
(c.f. 360 for C-C)

Hybridisation
Alkene carbons are sp2-hybridised
Two p and one s orbitals are mixed to give
three sp2 hybrid orbitals
The sp2 orbitals have a trigonal planar
arrangement, with the remaining p orbital
perpendicular to the plane

Bonding
Head-to-head overlap of sp2 bybrid orbitals gives rise to a (sigma) bond
Sideways overlap of the p orbitals gives rise to a (pi) -bond
The -bond is weaker than the -bond due to less efficient orbital
overlap

Naming
Alkene names end in ene

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Isomers are possible with >3C

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Isomers
Stereoisomers are possible due to lack of rotation about C=C bond

Stereoisomers
diastereomers (non-mirror-image
stereoisomers)
cis-trans
isomers,
geometric
isomers

How would we classify/name these isomers?

Structural requirements for alkene diastereomers

Each end of the C=C bond must have two different groups (i.e., AB,
DE) (but A & B can be the same as D & E)

Cant classify these as cis-trans isomers as they are trisubstituted

Require an alternative naming system

19

Lecture 7
E/Z-nomenclature of alkenes
Rules for assigning E/Z-stereochemistry of alkenes very similar to R/Sstereochemistry of stereogenic carbon atoms

Rules for assigning E/Z

Rule 1:
o Assign priorities to the groups at each end of the double bond
(i.e. high/low at left end, high/low at right end) in same way as
for R/S-designations (Cahn-Ingold-Prelog rules)

20

Rule 2:
o If the high priority groups are one the same side (Z)o If the high priority groups are one the opposite side (E)-

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
Alkene isomerisation in biology

Aromatic compounds
Historically, aromatic
distinctive odours

compounds were so named due to their

It was soon realised that these compounds differed in their chemical

behaviour from other classes of organic compounds (such as alkanes,
alkenes)
Aromatic compounds now refer to benzene and its structural relatives

Benzene
Stability

Structure

21

Benzene is a regular hexagon; all C-C bonds are the same length
(139 pm; intermediate between a C-C single bond (154 pm) and a
C=C double bond (134 pm)).

Benzene is planar, all bond angles 120

Benzene: Reactivity

H2 / Pd(cat.)

rapid
reaction
at,
ambient temp., pressure

slow reaction at
temp., pressure

Br2

rapid
bromination
(addition reaction)

no reaction (substitution
occurs) if catalyst added

Benzene does not behave like an alkene!

22

high

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Lecture 8
Benzene: Structure
Proposed structures of benzene:

Kekules drawing of the resonance forms of benzene (1872);

Benzene: Resonance stabilisation

The two representations of benzene are resonance forms

Neither is a strictly correct - the real structure of benzene is a
hybrid of the resonance forms
The -electrons are not localised between specific carbon atoms they are delocalised

The circle representation of benzene is sometimes used to represent

the delocalised electrons, but it is limited in that it doesnt indicate
how many -electrons are in the ring

Benzene: Resonance

Individual resonance forms are imaginary, not real

o the real form is an average, or resonance hybrid, of the different
forms
Resonance forms differ only in the placement of the - or nonbonding electrons
o neither the position nor hybridisation of any atom changes
Resonance forms must obey the normal rules of valency
o be careful to assign correct charges and number of bonds
Different resonance forms don t have to be equivalent

23

The resonance hybrid is more stable than individual resonance forms

Orbital description
6 sp2-hybridised carbons
each has a p-orbital with
one electron

The two resonance forms conjure

images of p-orbital overlap only to
one side or the other...

Requirements for aromaticity

Cyclic
Conjugated
(alternating double and single
bonds)
Planar

24

But the resonance hybrid is better

visualised as having the p-orbitals
overlapping on both sides, resulting in
delocalised electron clouds above and
below the ring.

each atom ring is sp2-hybridised

necessary for overlap of p-orbitals

4n+2 -electrons (the Hckel rule) (n = integer)

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Heterocyclic aromatics

Nomenclature

Some aromatic compounds have retained their historic trivial names

25

26

Others are names by a more systematic approach

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
Disubstituted benzenes
1,2-disubstituted benzene
ortho-substituted
(Greek; straight)

1,3-disubstituted benzene
meta-substituted
(Greek; after)

1,4-disubstituted benzene
para- substituted
(Greek; beyond)

2-nitrophenol
ortho-nitrophenol
(o-nitrophenol)

3-bromobenzoic acid
meta-bromobenzoic acid
(m-bromo...)

1-iodo-4-nitrobenzene
p-iodonitrobenzene

(p-iodo...)

27

Lecture 9
Alkynes
Alkynes have the general formula CnH2n-2

Geometry
Contain CC double bond
Linear arrangement of atoms

CC bond length 1.20

CC bond strength 840 kJ.mol-1

Sp hybridisation

One p and one s orbital are mixed

to give two sp hybrid orbitals
The sp orbitals have a linear
arrangement, with the remaining
two p orbitals perpendicular to
these and each other

Bonding
Head-to-head overlap of sphybrid orbitals gives rise to a (sigma) bond
Sideways overlap of two sets of p orbitals gives rise to two
perpendicular -bonds

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Naming
Alkyne names end in yne

Numbers used to define position of triple bond (as for alkenes)

Other sp-hybridised molecules

Carbon dioxide

Allenes

Functional groups
C-C and C-H bonds are strong and non-polar, and are therefore
relatively unreactive
The more reactive bond types/groupings are termed functional groups;
e.g. carbon-carbon multiple bonds
o alkenes (C=C)
o alkynes (CC)
o aromatic compounds
functional groups incorporating heteroatoms (non-C,H)

29

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

31

Lecture 10
1, 2, 3, 4 centres
Carbon can have up to four other carbons attached (referring to sp3carbons only)
o 1 C-C bond

primary carbon (1)

o 2 C-C bonds

secondary carbon (2)

o 3 C-C bonds

tertiary carbon (3)

o 4 C-C bonds

quaternary carbon (4)

1, 2, 3 functional groups
A functional group attached to a 1 centre is referred to as a 1
functional group (and so on) (most commonly for alcohols & alkyl
halides)
tertiary
(3)
alcohol
Secondary
(2)
alcohol
primary
(1)
alcohol

secondary
bromide

(2)

alkyl

tertiary (3)
alkyl
chloride

primary (1)
alcohol

Structure determination and spectroscopy

How do we determine the structure of a compound isolated from
natural sources or synthesised in the laboratory?
Various spectroscopic/spectrometric techniques provide information
about structure;
o mass spectrometry: molecular weight/formula
o UV spectroscopy: conjugated systems
o IR spectroscopy: functional groups
o NMR spectroscopy: C/H framework
Mass spectrometry
The compound is vaporised and ionised by one of several techniques
Traditionally, irradiation by an electron beam is used to generate a
radical cation (molecular ion, M+)

32

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

The molecular ion can break down into fragment or daughter ions
The ions are separated according to their mass (m) and charge (z)

Mass spectrometer

Simple mass spectra

33

Mass spectrum of hexane

Mass spectrum of 2,2-dimethylpropane

The mass spectrum of 2,2-dimethylpropane has a very weak molecular
ion at m/z = 72, but a strong peak at m/z = 57.
The loss of a methyl group (15) gives rise to a very stable carbocation

The Electromagnetic Spectrum

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

UV Spectroscopy

Conjugated systems absorb light in the UV region

Electron excited from * orbital
The greater the conjugation, the lower the energy required, and
therefore the greater the wavelength
Highly conjugated systems can absorb in the visible region (>400 nm),
giving rise to coloured compounds

UV Spectra

35

butadiene:
hexatriene:
octatetraene:
benzene:

max
nm

217

max
nm

258

max
nm

-carotene:
290

max = 206,
254 nm

36

max = 455 nm

(absorbs in the blue region, resulting in

an orange colour)

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Lecture 11
IR Spectroscopy

In infra-red (IR) spectroscopy, the frequency of the absorbed radiation

is given in terms of the units
reciprocal cm
(cm-1) (also called
wavenumbers )
IR range: 4000 400 cm-1 (2.5 25m)

IR radiation corresponds to the energy of molecular vibrations

(stretching, bending)
Energy is absorbed if the frequency of radiation matches the frequency
of the vibration (resulting in increased amplitude of vibration)
Different bond types have specific frequencies of vibration: IR
spectrocopy gives us information about the functional groups present
in a molecule

Characteristic IR absorptions

Alkyl groups (C-H)

2800-3000

ignore!
(in
most
organic compounds)

Alcohols (O-H)

3400-3600

Amines (N-H)

3300-3500

similar to O-H

Carbonyl compounds
(C=O)

1670-1780

contained
in
many
functional groups e.g.
esters,
amides,

37

fingerprint region

<1500

ketones etc.
used only to match
identical compounds

IR Spectra

Structure of an unknown

Mass spectrum indicates MW=60

o Possible molecular formula: C3H8O
o Major fragment ion m/z = 45 (loss of 15; -CH3)

IR spectrum indicates OH group (strong, broad peak ~ 3350 cm-1)

o no C=O at ~ 1700 cm-1
Most probably 2-propanol
o stable fragment ion;
Need more data for definitive structure
determination

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Structure determination and spectroscopy

How do we determine the structure of a compound isolated from
natural sources or synthesised in the laboratory?
Various spectroscopic/spectrometric techniques provide information
about structure;
o mass spectrometry: molecular weight/formula
o UV spectroscopy: conjugated systems
o IR spectroscopy: functional groups
o NMR spectroscopy: C/H framework
Nuclear magnetic resonance (NMR)
Many types of nuclei have a spin, and because they are charged, they
therefore act as tiny bar magnets!
In the presence of an external field, the nuclei can either be aligned
with or against the applied field

These spin states are of slightly different energies. If they are irradiated
with the appropriate frequency, the nuclei of the low-energy state
absorb the energy and spin-flip to the high energy state.
Typically, superconducting magnets of 5-12 tesla (T) are used, requiring
radiowaves (200-500 MHz) for resonance

1H and 13C nuclei are most commonly used, as they allow for a map
of the carbon-hydrogen framework of a molecule to be determined
Only 1% of carbon nuclei are 13C, so carbon NMR spectroscopy is less
sensitive that hydrogen NMR (proton NMR) spectroscopy

NMR Spectroscopy
The radiofrequency required to bring a nucleus into resonance is
proportional to the strength of the magnetic field.
However, every nucleus is surrounded by electrons which set up tiny
local magnetic fields
Each type of nucleus resonates at a slightly different frequency (the
differences are in parts per million, ppm!), depending on the effective
field at each nucleus.

39

Beffective =

Bapplied Blocal

NMR spectrum provides information of the number and type of H or C

environments

1H and 13C NMR spectra of methyl acetate

6 hydrogens in total, but

only
two
different
environments: all Hs in a
CH3
group
are
equivalent
Tetramethylsilane (TMS,
(CH3)4Si) is used as a
reference
and
is
arbitarily set to 0 ppm
3 carbon atoms all are
different, giving 3 peaks

13C NMR spectroscopy

The most common form of 13C NMR spectroscopy, proton-decoupled
13C NMR, removes interference from neighbouring hydrogens and
gives a separate signal for each different carbon environment
The number of carbon environments is determined by elements of
symmetry present in the molecule
The position of each signal is determined by the electronegativity of
nearby atoms, and other factors

40

Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

41

Lecture 12
13C NMR spectroscopy

Shows number of non-equivalent hydrogens

Size of each peak (integration of area under each peak) is proportional
to the number of hydrogens in each environment

Peak Integration
bromoethane
2 signals
ratio 2 : 3

2bromopropane
2 signals
ratio 1 : 6

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4
Spin-spin coupling

The position a signal occurs in

the spectrum (the chemical
shift) is determined by the
effective magnetic field at that
hydrogen nucleus.
But each hydrogen is itself
acting as a tiny magnet; each H
is therefore affected by the
other H atoms around it.
The signal is split into multiple
lines as the nearby hydrogens
can be aligned with or against
the applied magnetic field,
slightly varying the effective field
n+1 rule
o Number of lines observed for a hydrogen with n hydrogens on
adjacent atoms is n + 1
o The ratio of the intensities of the lines making up the multiplet is
given by Pascal s triangle:

Distance between peaks in a multiplet is the coupling constant

(denoted J, measured in Hz)

1H NMR spectroscopy is a very powerful technique:

43

Number of different H-environments

o Number of peaks
Type of H-environment (nearby functional groups)
o position of peak (chemical shift, )
Number of equivalent H s in each environment
o integration of peak area
Number of adjacent H s
o spin-spin coupling, n+1 rule

IR spectrum: C=O, no OH
UV spectrum:
system

highly

conjugated

Mass spectrum: MW = 136

C8H8O2 fragments 107 (29, loss of
Et or CHO)
92 (further 15, Me)
13C NMR: 6 peaks (some symmetry)
1H NMR: CH singlet (no adj H)
2 doublets (CH-CH)
CH3 singlet (no adj H)
IR spectrum: C=O, no OH
UV spectrum: highly conjugated system
Mass spectrum: MW = 136
C8H8O2
fragments 107 (29, loss of Et or CHO)
92 (further 15, Me)

Magnetic resonance imaging (MRI)

1H NMR of the body
Detects water content/environment

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Organic Chemistry Chemistry 1

Weeks 1, 2, 3 & 4

Complementary to X-ray (visualises soft tissue rather than hard tissue)

Used to detect tumours, Alzheimers, sports injuries, etc.
Pioneers (Profs Paul Lauterbur & Peter Mansfield) awarded 2003 Nobel
Prize in medicine

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