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N H
N O
N
N
H3C S O
N
O
N
H3C
N H
N O
N
N
H3C S O
N
O
N
H3C
OH
NH2
2-amino-4-methylpentanoic acid
OH
NH2
2-amino-4-methylpentanoic acid
OH
NH2
2-amino-4-methylpentanoic acid
the prefix can
become a nightmare
as it contains most
information
CH3 CH3
OH
H3C CH3 H3C 4 2
5 3 1
4-methylheptane 2-propyl-1-pentanol
1
parent
longest carbon
chain containing a
functional group
CH3 CH3
now use pent- as OH
H3C we have to start
CH3 H3C 4 2
5 3 1
our chain from the
4-methylheptane
functional group 2-propyl-1-pentanol
2
suffix
major
functional
group
list of major
groups pg 13
order of priority
pg 14
O CH3 O
O CH3 O
O
HO
H3C CH3
O
2-pentanone 5-methylheptanoic acid
pentan-2-one
NOT 4-pentanone
3
position
of functional
group from
end of chain
O
HO ...giving major
H3C CH3 functional group
lowest possible
O value
2-pentanone 5-methylheptanoic acid
pentan-2-one
NOT 4-pentanone
3
position
of functional
group from
end of chain
it doesn’t matter
O where number
HO goes but I think the
H3C CH3 second example
avoids confusion
O later
2-pentanone 5-methylheptanoic acid
pentan-2-one
NOT 4-pentanone
4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
H3C CH3
H3C CH3
H3C CH3 CH3
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
numbering should
H3C CH3 start with major
H3C CH
functional group3
H3C CH3 (like previous
CH3 slide)
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
H3C CH3
H3C CH3
H3C CH3 CH3
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
if no major functional
group then have
lowest numbering for
the majority of
substituents
4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
H3C CH3 note: group identical
H3C substituentsCH
(or 3
functional groups)
H3C CH3 CH3
together
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
H3C CH3
H3C CH3
H3C CH3 CH3
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
so trimethyl not 2-
methyl-2-methyl-6-
methylheptane
4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
H3halides
bizarrely, C don’t CH3
count as functional H3C CH3
groups...don’t
H3C ask...
CH3 CH3
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane
5
functional groups FG
principle FG suffix &
numbering; all others
prefix
O O CH3
H3C OH
HO OH
H3C CH3 O
5-hydroxy-2,2-dimethyl 2-methyl-4-oxo
pentanoic acid hex-2-enoic acid
O O CH3
H3C OH
HO OH
H3C CH3 O
5-hydroxy-2,2-dimethyl 2-methyl-4-oxo
pentanoic acid hex-2-enoic acid
O O CH3
major functional
group is suffix and
H3isC OH
HO OH the start of
numbering
H3C CH3 O
5-hydroxy-2,2-dimethyl 2-methyl-4-oxo
pentanoic acid hex-2-enoic acid
O O CH3
H3C OH
all other groups
HO OH are prefix
H3C CH3 O
5-hydroxy-2,2-dimethyl 2-methyl-4-oxo
pentanoic acid hex-2-enoic acid
O O CH3
H3C OH
HO OH
H3C CH3 O
5-hydroxy-2,2-dimethyl 2-methyl-4-oxo
pentanoic acid hex-2-enoic acid
H3C O
Br N
CH3 O
1-bromo-2-methylpropane nitroethane
7
order
a, b, c...hope
you know prefixes are ordered
alphabetically
your alphabet! (although descriptors
like tert are ignored)
NH
HO OH
3-hydroxy-2-(methylamino)pentanoic acid
NOT 2-(methylamino)-3-hydroxypentanoic
acid
name this
molecule...
OH O
H3C N CH3
H
hept
1
parent
OH O
H3C N CH3
H
select longest
carbon chain (with
major functional
1
group in it)
parent
OH O
H3C N CH3
H
amide
2
suffix
hept
identify major
functional group –
this will be the
suffix
6 OH O
H3C 5 3 1 N CH3
4 2 H
number chain
starting with major
3
functional group
hept amide
position
6 OH O
H3C 5 3 1 N CH3
4 2 H
5-methyl
4
prefix
hept amide
add prefixes (and
remember to tell us
where they are by giving
a position number)
6 OH O
H3C 5 3 N1 CH3
4 2 H
3-hydroxy 6-en
5
functional groups
functional groups
and the last bit (which
throws a nasty curve
ball in but don’t
worry...)
6 OH O
H3C 5 3 1 N CH3
4 2 H
N-ethyl
6
the rest
hept amide 5-methyl 3-hydroxy 6-en
OH O
H3C N CH3
H
N-ethyl-3-hydroxy-5-methylhept-6-enamide
7
order
OH O
H3C N CH3
H
N-ethyl-3-hydroxy-5-methylhept-6-enamide
to be honest order
7
not too important
as long as name is
not ambiguous
order
N-ethyl?
(methylamino)?
what the
©Renaissance Pictures
@&!!#?
DON’T
PANIC !
only simple examples in test
draw the molecule
with the following
name...
4-ethyl-3-hydroxycyclohexanone
4-ethyl-3-hydroxycyclohexanone
1 parent
4-ethyl-3-hydroxycyclohexanone
2 suffix
4-ethyl-3-hydroxycyclohexanone
4
H3C
prefix
4-ethyl-3-hydroxycyclohexanone
numbering starts
from major functional
group
O
1
2
3
4
4
H3C
prefix
4-ethyl-3-hydroxycyclohexanone
O
1
2
3
4 OH
5
H3C
functional groups
functional groups
H C H
H
methane
CH4
propane
C3H8
CnH2n+2
alkanes
H
H C H
H
methane
CH4
propane
open chains (no C3H8
rings) have this
general formula
CnH2n+2
alkanes
H
H C H
H
methane
CH4
alkanes are
tetrahedral in
shape...we shall see
why later
propane
C3H8
CnH2n+2
alkanes
H
H C H
H
methane
CH4
alkanes are
boring...normally
fuels or solvents
propane
C3H8
CnH2n+2
structural
isomers
same number of
atoms – but bonding
different
H H
H H
ethene
trigonal planar
alkenes
H H
ethene
trigonal planar
alkenes
means it is flat with
three groups
attached to central
atom
H H
H H
ethene
trigonal planar
configurational
(stereoisomers)
isomers
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
these 2 are
stereoisomers. Same
1-butene
atoms and bonds but 2-methylpropene cyclobutane
C4different
H8 orientation in C4H8 C4H8
space
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
H3C CH3
CH3
H3C
CH3
H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
α-pinene
alkenes
in nature
H3C CH3
CH3
H3C
CH3
H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
α-pinene
yup...it smells of
pine...and is a very
useful compound in
chemistry
alkynes
H H
triple bond makes
ethyne alkynes long
C2H2 cylinders
O
O
OMe O
O O
H3C O
OH O
MeHN
HO
O
CH3
OH
neocarzinostatin chromophore A
alkynes
H H
ethyne
C2H2
O
they are found in O
nature...this nasty OMe O
beast cleaves DNA
O O
H3C O
OH O
MeHN
HO
O
CH3
OH
neocarzinostatin chromophore A
cyclic compounds
cyclohexane benzene
C6H12 C6H6
cyclic compounds
some cyclic
molecules are
flat...because they
have flat double
bonds
cyclohexane benzene
C6H12 C6H6
cyclic compounds
cyclohexane benzene
C6H12 C6H6
cyclic structures
in nature
H3C
CH3
CH3 H CH3
H H H3C
(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-(6-
methylheptan-2-yl)-hexadecahydro-1H-
cyclopenta[a]phenanthrene
cholestane - steroid
alcohols
OH
ethanol
C2H6O
alcohols
need OH attached to
alkane (not alkene,
alkyne or benzene)
OH
ethanol
C2H6O
alcohols
found in many
biological systems...
OH
ethanol
C2H6O
alcohols ...especially on
Saturday nights...
OH
ethanol
C2H6O
alcohols in
the real world
HO
O or Sunday HO
HO mornings... OH
HO OH
HO
6-(hydroxymethyl)-tetrahydro- 1,2-ethandiol
2H-pyran-2,3,4,5-tetraol ethylene glycol
glucose antifreeze
sugar I guess!
three classes
of alcohol H3C
CH3
CH3 CH3
secondary (2°)
CH3 H CH3
H3C OH
H H H3C
primary (1°) HO
(R)-3,7-dimethyloct-6-en-1-ol cholesterol
citronellol all animals
citronella oil CH3
tertiary (3°)
H3C OH
CH3
(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil
three classes
of alcohol H3C
CH3
CH3 CH3
secondary (2°)
CH3 H CH3
H3C OH
H H H3C
primary (1°) HO
(R)-3,7-dimethyloct-6-en-1-ol cholesterol
citronellol all animals
citronella oil CH3
tertiary (3°)
H3C OH
CH3
(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil
three classes
of alcohol H3C
CH3
CH3 CH3
secondary (2°)
CH3 H CH3
H3C OH
H H H3C
primary (1°) HO
(R)-3,7-dimethyloct-6-en-1-ol cholesterol
citronellol all animals
citronella oil CH3
H3C
OH HO
H
H3C N
O
phenol O
carbolic acid
(E)-N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-6-enamide
capsaicin
chilli peppers
phenols looks like an
alcohol BUT is not
(as it is not
CH3 to an
attached
alkane)
H3C
OH HO
H
H3C N
O
phenol O
carbolic acid
(E)-N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-6-enamide
capsaicin
chilli peppers
phenols thus has very
different
properties...I should CH3
whistle ‘ring of fire’
now...
H3C
OH HO
H
H3C N
O
phenol O
carbolic acid
(E)-N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-6-enamide
capsaicin
chilli peppers
ethers
O
O O
O
H3C O CH3
O O
ethoxyethane O
diethyl ether tetrahydrofuran
ether THF 18-crown-6
replace one carbon
in an alkyl chain and
you have an ether.
Often used as
solvents
18-crown-6
and potassium
cation
halides organic molecules
containing fluorine,
chlorine, bromine or
iodine
H F
Cl H Cl F
Cl Cl
dichloromethane dichlorodifluoromethane
DCM Freon (refrigerant)
a CFC
Cl Cl
Cl
Cl
O
Cl H
Cl
H
dieldrin
Pic: NASA
halides often toxic and some
are responsible for
the hole in the ozone
H F layer
Cl H Cl F
Cl Cl
dichloromethane dichlorodifluoromethane
DCM Freon (refrigerant)
a CFC
Cl Cl
Cl
Cl
O
Cl H
Cl
H
dieldrin
Pic: NASA
thiols
SH
HS SH CH3 O
HS
H2N H H3C CH3 H3C CH3
CO2H
(R)-2-amino-3- propane-2,2-dithiol 4-methyl-4-
sulfanylpropanoic acid sulfanylpentan-2-one
cysteine these are the
sulfur version of
alcohols...found in
nature (and us)
thiols
SH
HS SH CH3 O
HS
H2N H H3C CH3 H3C CH3
CO2H
(R)-2-amino-3- propane-2,2-dithiol 4-methyl-4-
sulfanylpropanoic acid sulfanylpentan-2-one
cysteine
one of these is the
smelliest chemical
known...but no one wants
to repeat the experiment
to find out which!
CH3
2x10 -5 ppb
HS
H3C
CH3
2-(4-methylcyclohex-3-
enyl)propane-2-thiol
taste of grapefruit
2x10 -5 ppb
HS
H3C
CH3
2-(4-methylcyclohex-3-
enyl)propane-2-thiol
taste of grapefruit
this value is similar to
1 drop in a lake...
amines
CH3
H3C N NH2
H2N H2N NH2
CH3
triethylamine butane-1,4-diamine pentane-1,5-diamine
smells of fish putrescine cadaverine
smells of decay smells of decay
O CH3 O
OH H3C OH
H2N H NH2
(S)-2-amino-3- (S)-2-amino-3-
phenylpropanoic acid methylbutanoic acid
phenylalanine valine
amino acid amino acid
O
methyl 3-(benzoyloxy)-8-methyl-
8-aza-bicyclo[3.2.1]octane-2-
carboxylate
cocaine
O
methyl 3-(benzoyloxy)-8-methyl-
8-aza-bicyclo[3.2.1]octane-2-
carboxylate
cocaine
H H3C N CH
H N H H3C NH2 N 3
H H3C CH3 H3C
ammonia methylamine dimethylamine trimethylamine
1° amine 2° amine 3° amine
H3C N CH
3
H3C
trimethylammonium ion
4° ammonium (salt)
five kinds of amine
H H3C N CH
H N H H3C NH2 N 3
H H3C CH3 H3C
ammonia methylamine dimethylamine trimethylamine
1° amine 2° amine 3° amine
H but primary,
secondary & tertiary
H3C N CH mean something
3 different than when
H3C
we used them with
trimethylammonium ion alcohols!
4° ammonium (salt)
five kinds of amine
H H3C N CH
H N H H3C NH2 N 3
H H3C CH3 H3C
ammonia methylamine dimethylamine trimethylamine
1° amine 2° amine 3° amine
H
...now refer to the
number of C attached H3C N CH
to the N...but it gets 3
worse...
H3C
trimethylammonium ion
4° ammonium (salt)
the problem
with amines primary amine
because only 1
primary amine carbon attached
(1°)
NH2
H3C OH
CH3 O
secondary position
(2°)
the problem
with amines but in a secondary
primary amine
position (like alcohol
(1°)naming) as this carbon
has 2 carbons
attached!
NH2
H3C OH
CH3 O
secondary position
(2°)
carbonyl:
aldehydes O
O O
H
H H H3C H
OH OH
O
HO
OH OH H
(2R,3S,4R,5R)-2,3,4,5,6-
pentahydroxyhexanal
glucose
carbonyl:
aldehydes O
O O
H
H H H3C H
H3C CH3
H3C H H CH3
H3C CH3
H3C H H CH3
aspartame
sweetener
amide
how are functional
groups related?
H oxidation H oxidation H oxidation OH
R C H R C H R C R C
reduction reduction reduction
H OH O O
hydrocarbon alcohol aldehyde carboxylic
acid
carboxylic acids
alcohols
esters
ethers
aldehydes amides
alkanes amines
ketones acyl halides
halides
acid anhydrides
thiols
nitriles
parts 3 & 4
are combined
word of
warning...next 2
units will not be in
the same order as
study guide...
what have
....we learnt? • naming (simple)
HO molecules
HO
• recognise
functional groups
OH
Me O
Me O O
NH2 O
Cl
OH O O
HO Cl OH
O O O
H H
O N N NHMe
N N N
H H H
HN O O O Me
molecules may look
HO2C complicated but simply
NH2 Me into
break them down
their functional groups
OH (amides in red)
HO OH
Vancomycin