how are molecules named - organic chemistry from examville.com
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Unit One Part 2:naming & functional groups
N
N
N
N
SN
NH3C
H3C
O
O
CH3
H3CO
O
H
viagra (trade name)
sildenafil (trivial name)
5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1-
methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
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Unit One Part 2:naming & functional groups
N
N
N
N
SN
NH3C
H3C
O
O
CH3
H3CO
O
H
viagra (trade name)
sildenafil (trivial name)
5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1-
methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
Dont panic!
We wont do anything
this complicated
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Unit One
Part2
Namingmolecules (pg 11-16)Introducing functional
groups (pg 16-9)remember...read the
study guide it
contains all you need
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how do wename molecules?
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NH2
O
OH
2-amino-4-methylpentanoic acid
prefixsubstituents
minor functionalgroups
parentcarbon chain
(& multiplebonds)
suffixprincipalfunctional
groups
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NH2
O
OH
2-amino-4-methylpentanoic acid
prefixsubstituents
minor functionalgroups
parentcarbon chain
(& multiplebonds)
suffixprincipalfunctional
groups
there are three parts
to any name...even
Viagras real name
obeys this.
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NH2
O
OH
2-amino-4-methylpentanoic acid
prefixsubstituents
minor functionalgroups
parentcarbon chain
(& multiplebonds)
suffixprincipalfunctional
groups
the prefix can
become a nightmare
as it contains most
information
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sevensteps tosuccess!
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sevensteps tosuccess!
works for all
molecules but thewhole system takes
volumes to
explain...
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parentlongest carbon
chain containing afunctional group1H3C CH3
CH3
4-methylheptane
H3C
CH3
OH
2-propyl-1-pentanol
1
2
3
4
5
page 12 of guide
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parentlongest carbon
chain containing afunctional group1H3C CH3
CH3
4-methylheptane
H3C
CH3
OH
2-propyl-1-pentanol
1
2
3
4
5
7 bigger than 5 he
says patronisingly
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parentlongest carbon
chain containing afunctional group1H3C CH3
CH3
4-methylheptane
H3C
CH3
OH
2-propyl-1-pentanol
1
2
3
4
5
now use pent- aswe have to start
our chain from the
functional group
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suffixm a j o r
functionalg r o u p
H3C OH
O
butanoic acid
H3C NH2
OCH3
3-methylbutanamide
2 list of majorgroups pg 13order of priority
pg 14
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suffixm a j o r
functionalg r o u p
H3C OH
O
butanoic acid
H3C NH2
OCH3
3-methylbutanamide
2only one major
group per
molecule
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H3C CH3
O
2-pentanonepentan-2-one
NOT 4-pentanone
O
HO
5-methylheptanoic acid
positionof functional
group fromend of chain3 number longestchain (parent)from start tofinish...
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H3C CH3
O
2-pentanonepentan-2-one
NOT 4-pentanone
O
HO
5-methylheptanoic acid
positionof functional
group fromend of chain3...giving major
functional group
lowest possible
value
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H3C CH3
O
2-pentanonepentan-2-one
NOT 4-pentanone
O
HO
5-methylheptanoic acid
positionof functional
group fromend of chain3it doesnt matterwhere number
goes but I think the
second exampleavoids confusion
later
fi
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H3C CH3
CH3
CH3
Cl
8-chloro-2,3-dimethylnonaneNOT 2-chloro-7,8-dimethylnonane
H3C CH3
H3C CH3
CH3
2,2,5-trimethylheptaneNOT 3,6,6-trimethylheptane
prefixsubstituents(and minor
functionalg r o u p s )4
fi
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H3C CH3
CH3
CH3
Cl
8-chloro-2,3-dimethylnonaneNOT 2-chloro-7,8-dimethylnonane
H3C CH3
H3C CH3
CH3
2,2,5-trimethylheptaneNOT 3,6,6-trimethylheptane
prefixsubstituents(and minor
functionalg r o u p s )4numbering should
start with majorfunctional group
(like previous slide)
fi
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H3C CH3
CH3
CH3
Cl
8-chloro-2,3-dimethylnonaneNOT 2-chloro-7,8-dimethylnonane
H3C CH3
H3C CH3
CH3
2,2,5-trimethylheptaneNOT 3,6,6-trimethylheptane
prefixsubstituents(and minor
functionalg r o u p s )4
if no major functional
group then have
lowest numbering for
the majority ofsubstituents
fi
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H3C CH3
CH3
CH3
Cl
8-chloro-2,3-dimethylnonaneNOT 2-chloro-7,8-dimethylnonane
H3C CH3
H3C CH3
CH3
2,2,5-trimethylheptaneNOT 3,6,6-trimethylheptane
prefixsubstituents(and minor
functionalg r o u p s )4note: group identical
substituents (or
functional groups)
together
fi
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H3C CH3
CH3
CH3
Cl
8-chloro-2,3-dimethylnonaneNOT 2-chloro-7,8-dimethylnonane
H3C CH3
H3C CH3
CH3
2,2,5-trimethylheptaneNOT 3,6,6-trimethylheptane
prefixsubstituents(and minor
functionalg r o u p s )4
so trimethyl not 2-methyl-2-methyl-6-
methylheptane
fi
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H3C CH3
CH3
CH3
Cl
8-chloro-2,3-dimethylnonaneNOT 2-chloro-7,8-dimethylnonane
H3C CH3
H3C CH3
CH3
2,2,5-trimethylheptaneNOT 3,6,6-trimethylheptane
prefixsubstituents(and minor
functionalg r o u p s )4bizarrely, halides dont
count as functional
groups...dont ask...
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CH3
OH
O
O
H3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH3
5-hydroxy-2,2-dimethylpentanoic acid
functional groups FGprinciple FG suffix &
numbering; all othersprefix5
multiple bonds combined with parent
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CH3
OH
O
O
H3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH3
5-hydroxy-2,2-dimethylpentanoic acid
functional groups FGprinciple FG suffix &
numbering; all othersprefix5
multiple bonds combined with parent
functional groups
listed on pg 13
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CH3
OH
O
O
H3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH3
5-hydroxy-2,2-dimethylpentanoic acid
functional groups FGprinciple FG suffix &
numbering; all othersprefix5
multiple bonds combined with parent
major functionalgroup is suffix and is
the start of
numbering
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CH3
OH
O
O
H3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH3
5-hydroxy-2,2-dimethylpentanoic acid
functional groups FGprinciple FG suffix &
numbering; all othersprefix5
multiple bonds combined with parent
all other groups
are prefix
G
5
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CH3
OH
O
O
H3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH3
5-hydroxy-2,2-dimethylpentanoic acid
functional groups FGprinciple FG suffix &
numbering; all othersprefix5
multiple bonds combined with parent
alkenes and
alkynes are
normally part of
the parent
i FG
6
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BrH3C
CH3
1-bromo-2-methylpropane
minor FGnot all groups are
equal: halo- & nitro-(-NO2) are prefixes6N
O
O
nitroethane
d
7
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ordera, b, c...hope
y o u k n o wyour alphabet!7HO OH
O
NH
3-hydroxy-2-(methylamino)pentanoic acidNOT 2-(methylamino)-3-hydroxypentanoic
acid
prefixes are orderedalphabetically
(although descriptors
like tertare ignored)
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name thismolecule...
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H3C NH
O
CH3
OH
hept
1parent
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H3C NH
O
CH3
OH
1parent
select longest
carbon chain (with
major functional
group in it)
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H3C NH
O
CH3
OH
amide
2suffix heptidentify major
functional group
this will be the
suffix
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3position
H3C NH
O
CH3
OH
12
34
5
6
hept amide
number chain
starting with major
functional group
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H3C NH
O
CH3
OH
12
34
5
6
5-methyl
4prefix hept amideadd prefixes (and
remember to tell us
where they are by giving
a position number)
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5functional groups
H3C NH
O
CH3
OH
12
34
5
3-hydroxy6-en
6
hept amide 5-methyl
repeat with all
remaining
functional groups
and the last bit (which
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H3C NH
O
CH3
OH
12
34
5
N-ethyl
6
6the resthept amide 5-methyl 3-hydroxy6-en
(
throws a nasty curve
ball in but dont
worry...)
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7order
H3C NH
O
CH3
OH
N-ethyl-3-hydroxy-5-methylhept-6-enamide
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7order
H3C NH
O
CH3
OH
N-ethyl-3-hydroxy-5-methylhept-6-enamide
to be honest order
not too important
as long as name isnot ambiguous
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N-ethyl?
(methylamino)?
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what the
@&!!#?Renaissance Pictures
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DONTPANIC!
only simple examples in test
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draw the moleculewith the followingname...
4 th l 3 h d l h
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4-ethyl-3-hydroxycyclohexanone
4 th l 3 h d l h
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4-ethyl-3-hydroxycyclohexanone
1parent 4 th l 3 h d l h
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O
4-ethyl-3-hydroxycyclohexanone
2suffix 4 th l 3 h d l h
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O
4-ethyl-3-hydroxycyclohexanone
4prefix
O
H3C
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4 th l 3 h d l h
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O
H3C
OH
O
4-ethyl-3-hydroxycyclohexanone
5functional groups
1
2
3
4
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functional groups
these are listed on
pg 17
alkanes
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H
CH
H
H
methane
CH4
alkanes
CnH2n+2
propane
C3H8
alkanes
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H
CH
H
H
methane
CH4
alkanes
CnH2n+2
propane
C3H8open chains (norings) have this
general formula
alkanes
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H
CH
H
H
methane
CH4
alkanes
CnH2n+2
propane
C3H8
alkanes are
tetrahedral in
shape...we shall see
why later
alkanes
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H
CH
H
H
methane
CH4
alkanes
CnH2n+2
propane
C3H8
alkanes are
boring...normally
fuels or solvents
structural
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2,2-dimethylpropane
C5H12bp 9.6C
2-methylbutaneC5H12
bp 28C
pentaneC5H12
bp 36.2C
structuralisomers
structural
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2,2-dimethylpropane
C5H12bp 9.6C
2-methylbutaneC5H12
bp 28C
pentaneC5H12
bp 36.2C
structuralisomers
same number of
atoms but bonding
different
structural
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2,2-dimethylpropane
C5H12bp 9.6C
2-methylbutaneC5H12
bp 28C
pentaneC5H12
bp 36.2C
structuralisomers
can make bigdifferences in
properties...as
we shall see later
alkenes
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alkenes
trigonal planar
H
H H
H
ethene
alkenes
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alkenes
trigonal planar
H
H H
H
ethene
more exciting as the
double bond is
reactive!
alkenes
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alkenes
trigonal planar
H
H H
H
ethene
means it is flat withthree groups
attached to central
atom
configurational
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trans-2-buteneC4H8
H3C
CH3
H3C CH
3
cis-2-buteneC4H8
1-butene
C4H8
2-methylpropene
C4H8
cyclobutane
C4H8
configurational(stereoisomers)
isomers
no rotation around C=C bond configurational
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trans-2-buteneC4H8
H3C
CH3
H3C CH
3
cis-2-buteneC4H8
1-butene
C4H8
2-methylpropene
C4H8
cyclobutane
C4H8
configurational(stereoisomers)
isomers
no rotation around C=C bond
these 2 are structural
isomers
configurational
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trans-2-buteneC4H8
H3C
CH3
H3C CH
3
cis-2-buteneC4H8
1-butene
C4H8
2-methylpropene
C4H8
cyclobutane
C4H8
configurational(stereoisomers)
isomers
no rotation around C=C bond
these 2 are
stereoisomers. Sameatoms and bonds but
different orientation inspace
configurational
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trans-2-buteneC4H8
H3C
CH3
H3C CH
3
cis-2-buteneC4H8
1-butene
C4H8
2-methylpropene
C4H8
cyclobutane
C4H8
configurational(stereoisomers)
isomers
no rotation around C=C bond
occurs becomes
alkene cannotrotate
configurational
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trans-2-buteneC4H8
H3C
CH3
H3C CH
3
cis-2-buteneC4H8
1-butene
C4H8
2-methylpropene
C4H8
cyclobutane
C4H8
configurational(stereoisomers)
isomers
no rotation around C=C bond
a whole world of pain
is coming your way
when we discussstereoisomers!
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alkenes
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alkenesin nature
CH3
H3C
H3C
CH3
CH3H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept -2-ene-pinene
yup...it smells of
pine...and is a veryuseful compound in
chemistry
alkynes
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alkynes
O
O
O
O
O
O
O
H3C
OMe
OH
O
OH
HO
CH3
MeHN
neocarzinostatin chromophore A
H Hethyne
C2H2
triple bond makes
alkynes longcylinders
alkynes
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alkynes
O
O
O
O
O
O
O
H3C
OMe
OH
O
OH
HO
CH3
MeHN
neocarzinostatin chromophore A
H Hethyne
C2H2
they are found in
nature...this nasty
beast cleaves DNA
cyclic compounds
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cyclohexaneC6H12
cyclic compounds
benzene
C6H6
cyclic compounds
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cyclohexaneC6H12
cyclic compounds
benzene
C6H6
some cyclic
molecules are
flat...because they
have flat double
bonds
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cyclic structures
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yin nature
CH3
CH3
H3C
H3C
CH3
H H
H
(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-(6-methylheptan-2-yl)-hexadecahydro-1H-
cyclopenta[a]phenanthrene
cholestane - steroid
alcohols
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alcohols
OH
ethanol
C2H6O
alcohols
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alcohols
OH
ethanol
C2H6O
need OH attached to
alkane (not alkene,alkyne or benzene)
alcohols
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alcohols
OH
ethanol
C2H6O
found in manybiological systems...
alcohols...especially on
Saturday nights...
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alcohols
OH
ethanol
C2H6O
alcohols inh l ld
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HOOH
1,2-ethandiolethylene glycol
antifreeze
OHO
HO
HO
HO
OH
6-(hydroxymethyl)-tetrahydro-2H-pyran-2,3,4,5-tetraol
glucosesugar I guess!
the real world
or Sunday
mornings...
three classesf l h l
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H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-ol
citronellolcitronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterolall animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil
ofalcohol
tertiary (3)
secondary (2)
primary (1)
three classesf l h l
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H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-ol
citronellolcitronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterolall animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil
ofalcohol
tertiary (3)
secondary (2)
primary (1)
depends on the
number of carbons
attached to the
COH unit
three classesf l h l
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H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-ol
citronellolcitronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterol
all animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil
ofalcohol
tertiary (3)
secondary (2)
primary (1)
...this one has 1
carbon attached so isprimary. the next
has 2 so is
secondary etc.
three classesf l h l
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H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-ol
citronellolcitronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterol
all animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil
ofalcohol
tertiary (3)
secondary (2)
primary (1)
this controls thereactivity of the
alcohols as you
shall see in future
lectures
phenols
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phenols
OH
phenolcarbolic acid
HO
OH3C
H
N
O
CH3
H3C
(E)-N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-6-enamidecapsaicinchilli peppers
phenols
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phenols
OH
phenolcarbolic acid
HO
OH3C
H
N
O
CH3
H3C
(E)-N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-6-enamidecapsaicinchilli peppers
looks like an
alcohol BUT is not(as it is not
attached to an
alkane)
phenols
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phenols
OH
phenolcarbolic acid
HO
OH3C
H
N
O
CH3
H3C
(E)-N-(4-hydroxy-3-methoxybenzyl)-
8-methylnon-6-enamidecapsaicinchilli peppers
thus has very
different
properties...I should
whistle ring of firenow...
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halidesorganic molecules
containing fluorine,
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halidesH
HCl
Cl
dichloromethaneDCM
F
FCl
Cl
dichlorodifluoromethaneFreon (refrigerant)
a CFC
ClCl
Cl
ClCl
Cl H
H
O
dieldrin
Pic: NASA
g ,
chlorine, bromine or
iodine
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thiols
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thiols
H3
C CH3
H3C CH
3
HS SH OCH3HS
propane-2,2-dithiol 4-methyl-4-sulfanylpentan-2-one
H2N
SH
H
CO2H
(R)-2-amino-3-sulfanylpropanoic acid
cysteine these are thesulfur version of
alcohols...found innature (and us)
thiols
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thiols
H3
C CH3
H3C CH
3
HS SH OCH3HS
propane-2,2-dithiol 4-methyl-4-sulfanylpentan-2-one
H2N
SH
H
CO2H
(R)-2-amino-3-sulfanylpropanoic acid
cysteineone of these is the
smelliest chemicalknown...but no one wants
to repeat the experiment
to find out which!
CH3HS
2x10-5 ppb
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CH3
H3C
2-(4-methylcyclohex-3-enyl)propane-2-thioltaste of grapefruit
2x10 5 ppb
can smell nice...garlic,
truffles etc...And incredibly
small amounts are the tasteof grapefruit!
CH3HS
2x10-5 ppb
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CH3
H3C
2-(4-methylcyclohex-3-enyl)propane-2-thioltaste of grapefruit
2x10 5 ppb
this value is similar to
1 drop in a lake...
amines
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amines
CH3
NH3C
CH3
H2NNH2
triethylaminesmells of fish
butane-1,4-diamineputrescine
smells of decay
H2N
pentane-1,5-diaminecadaverine
smells of decay
NH2
...also smell bad but
are vital for life (and
the smell of death).
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amines in nature OCH3
NCH3
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O
O
O
methyl 3-(benzoyloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-
carboxylate
cocaine
Scarface (1983): Universal Pictures
but there is a problem
bigger than drugs...
five kinds ofamine
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NH
H
H
ammonia
H3
C NH2
methylamine1 amine
H3C
HN
CH3dimethylamine
2 amine
NCH
3
H3C
H3Ctrimethylamine
3 amine
NCH3
H3C
H3C
trimethylammonium ion
4 ammonium (salt)
H
five kinds ofamine
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NH
H
H
ammonia
H3C NH2
methylamine1 amine
H3C
HN
CH3dimethylamine
2 amine
NCH
3
H3C
H3Ctrimethylamine
3 amine
NCH3
H3C
H3C
trimethylammonium ion
4 ammonium (salt)
H but primary,secondary & tertiary
mean something
different than when
we used them with
alcohols!
five kinds ofamine
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NH
H
H
ammonia
H3C NH2
methylamine1 amine
H3C
HN
CH3dimethylamine
2 amine
NCH
3
H3C
H3Ctrimethylamine
3 amine
NCH3
H3C
H3C
trimethylammonium ion
4 ammonium (salt)
H...now refer to the
number of C attachedto the N...but it gets
worse...
the problemwith amines
primary amine
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with aminesprimary amine
(1)
secondary position
(2)
H3C OH
CH3 O
NH2
p ybecause only 1
carbon attached
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carbonyl:
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carbonyl:aldehydes
H H
O
methanalformaldehyde
H3C H
O
ethanalacetaldehyde
H
O
benzaldehyde
HOO
OH
OH
OH
OH
H
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
glucose
carbonyl:
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carbonyl:aldehydes
H H
O
methanalformaldehyde
H3C H
O
ethanalacetaldehyde
H
O
benzaldehyde
HO
O
OH
OH
OH
OH
H
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
glucose
C=O is the cornerstoneof organic synthesis.Aldehydes = CHO and
are more reactive than...
carbonyl:
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carbonyl:ketones
H3C CH3
O
propanoneacetone
CH3
H
O
H3C
(R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone(R)-carvone
spearmint
CH3
H
O
CH3
(S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone(S)-carvone
caraway
carbonyl:
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carbonyl:ketones
H3C CH3
O
propanoneacetone
CH3
H
O
H3C
(R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone(R)-carvone
spearmint
CH3
H
O
CH3
(S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone(S)-carvone
caraway
ketones, which haveC=O bonded to two
carbon groups
carboxylic acidd i ti id
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derivatives:acids
H3C OH
O
ethanoic acidacetic acid
vinegar
H3C
O
OH
OH
(S)-2-hydroxy-propanoic acid
L-(+)-lactic acid
O CH3
H3C CH3 CH3
CO2H
(2Z,4E)-3-methyl-5-(2,6,6-trimethyl-4-oxocyclohex-2-
enyl)penta-2,4-dienoic acidabscisic acidleaf fallC=O bonded to 1
carbon and an OHgroup
carboxylic acidd i ti th
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derivatives:others
H3C O
O
Na
sodium ethanoatecarboxylate ion
H3CO
CH3O
CH32-methylpropyl propanoate
isobutyl propionatesmell of rum
ester
HO2CHN
OMe
NH2
O
O
aspartamesweetener
amide
many different
derivativesdepending on what
is attached to C=O
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how arefunctional
groups related?
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what havewe learnt? naming (simple)
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NH
HN
HN
NH
HN
NH
NHMe
Me
Me
O
O
O
O
O
O O
O
NH2
OHHO
O
Cl
Cl
O
HO
HOOH
OOMe
NH2OH
Me
HO2C
O
....welearnt? naming(simple)molecules
recognisefunctional groups
molecules may look
complicated but simply
break them down into
their functional groups
top related