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Unit One Part 2:naming & functional groups
N
NNN
SN
NH3C
H3C O
O
CH3
H3C O
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
Unit One Part 2:naming & functional groups
N
NNN
SN
NH3C
H3C O
O
CH3
H3C O
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
Don’t panic!We won’t do anything
this complicated
Unit OnePart2Naming molecules (pg 11-16)Introducing functional groups (pg 16-9)
remember...read the study guide it
contains all you need
how do wename molecules?
NH2
O
OH
2-amino-4-methylpentanoic acid
prefixsubstituents
minor functional groups
parentcarbon chain
(& multiple bonds)
suffixprincipal functional
groups
NH2
O
OH
2-amino-4-methylpentanoic acid
prefixsubstituents
minor functional groups
parentcarbon chain
(& multiple bonds)
suffixprincipal functional
groups
there are three parts to any name...even Viagra’s real name
obeys this.
NH2
O
OH
2-amino-4-methylpentanoic acid
prefixsubstituents
minor functional groups
parentcarbon chain
(& multiple bonds)
suffixprincipal functional
groups
the prefix can become a nightmare as it contains most
information
five steps to success!
works for all molecules but the
whole system takes volumes to explain...
five steps to success!
parentlongest carbon chain containing a functional group1H3C CH3
CH3
4-methylheptane
H3C
CH3OH
2-propyl-1-pentanol1
23
45
page 12/13 of guide
parentlongest carbon chain containing a functional group1H3C CH3
CH3
4-methylheptane
H3C
CH3OH
2-propyl-1-pentanol1
23
45
7 bigger than 5 he says patronisingly
parentlongest carbon chain containing a functional group1H3C CH3
CH3
4-methylheptane
H3C
CH3OH
2-propyl-1-pentanol1
23
45
now use pent- as we have to start
our chain from the functional group
suffixm a j o r functional g r o u p
H3C OH
O
butanoic acidH3C NH2
OCH3
3-methylbutanamide
2 list of major groups pg 13
order of priority pg 14
suffixm a j o r functional g r o u p
H3C OH
O
butanoic acidH3C NH2
OCH3
3-methylbutanamide
2only one major
group per molecule
BrH3C
CH3
1-bromo-2-methylpropane
minor FGnot all groups are equal: halo- & nitro- (-NO2) are prefixes2
NO
O
nitroethane
a
no idea why!But please remember they are functional groups. It is only for naming that they
do not count
H3C CH3
O
2-pentanonepentan-2-one
NOT 4-pentanone
O
HO
5-methylheptanoic acid
positionof functional group from end of chain3 number longest
chain (parent) from start to
finish...
H3C CH3
O
2-pentanonepentan-2-one
NOT 4-pentanone
O
HO
5-methylheptanoic acid
positionof functional group from end of chain3
...giving major functional group lowest possible
value
H3C CH3
O
2-pentanonepentan-2-one
NOT 4-pentanone
O
HO
5-methylheptanoic acid
positionof functional group from end of chain3
it doesn’t matter where number
goes but I think the second example avoids confusion
later
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 functional g r o u p s ) 4
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 functional g r o u p s ) 4
numbering should start with major functional group
(like previous slide)
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 functional g r o u p s ) 4
if no major functional group then have
lowest numbering for the majority of substituents
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 functional g r o u p s ) 4
note: group identical substituents (or
functional groups) together
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 functional g r o u p s ) 4
so trimethyl not 2-methyl-2-methyl-6-
methylheptane
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 functional g r o u p s ) 4
bizarrely, halides don’t count as functional groups...don’t ask...
CH3
OH
O
OH3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH35-hydroxy-2,2-dimethyl
pentanoic acid
Prefixcontains everything except major functional group and multiple bonds4
multiple bonds combined with parent
CH3
OH
O
OH3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH35-hydroxy-2,2-dimethyl
pentanoic acid
Prefixcontains everything except major functional group and multiple bonds4
multiple bonds combined with parent
functional groups listed on pg 13
CH3
OH
O
OH3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH35-hydroxy-2,2-dimethyl
pentanoic acid
Prefixcontains everything except major functional group and multiple bonds4
multiple bonds combined with parent
major functional group is suffix and is
the start of numbering
CH3
OH
O
OH3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH35-hydroxy-2,2-dimethyl
pentanoic acid
Prefixcontains everything except major functional group and multiple bonds4
multiple bonds combined with parent
all other groups are prefix
CH3
OH
O
OH3C
2-methyl-4-oxohex-2-enoic acid
HO OH
O
H3C CH35-hydroxy-2,2-dimethyl
pentanoic acid
Prefixcontains everything except major functional group and multiple bonds4
multiple bonds combined with parent
alkenes and alkynes are
normally part of the parent
ordera, b, c...hope y o u k n o w your alphabet!5
HO OH
O
NH
3-hydroxy-2-(methylamino)pentanoic acidNOT 2-(methylamino)-3-hydroxypentanoic
acid
prefixes are ordered alphabetically
(although descriptors like tert are ignored)
name this molecule...
H3C NH
O
CH3
OH
hept
1parent
H3C NH
O
CH3
OH
1parent
select longest carbon chain (with major functional
group in it)
H3C NH
O
CH3
OH
amide
2suffixhept
identify major functional group –
this will be the suffix
3position
H3C NH
O
CH3
OH
12
34
5
6
hept amide
number chain starting with major
functional group
H3C NH
O
CH3
OH
12
34
5
6
5-methyl
4prefixhept amide
add prefixes (and remember to tell us
where they are by giving a position number)
4functional groups
H3C NH
O
CH3
OH
12
34
5
3-hydroxy 6-en
6
hept amide 5-methyl
repeat with all remaining
functional groups
H3C NH
O
CH3
OH
12
34
5
N-ethyl
6
4the resthept amide 5-methyl 3-hydroxy 6-en
and the last bit (which throws a nasty curve
ball in but don’t worry...)
5order
H3C NH
O
CH3
OH
N-ethyl-3-hydroxy-5-methylhept-6-enamide
5order
H3C NH
O
CH3
OH
N-ethyl-3-hydroxy-5-methylhept-6-enamide
to be honest order not too important
as long as name is not ambiguous
N-ethyl?
(methylamino)?
what the@&!!#?
©Renaissance Pictures
DON’TPANIC!
only simple examples in test
2exampleOn the next slide there
is a skeletal structure and four possible names.
Which is correct?
4-amino-3,5-dihydroxy-5-oxopentanoic acidA
4-amino-3,5,6-trihydroxyhexanoic acidB
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidD
OHC
OHOH
NH2OH
O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
4-amino-3,5,6-trihydroxyhexanoic acidB
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidDwrong
OHC
OHOH
NH2OH
O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
4-amino-3,5,6-trihydroxyhexanoic acidB
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidDwrong
OHC
OHOH
NH2OH
O
The parent contains 6 C. The carbon C of CHO still
counts!
B
4-amino-3,5-dihydroxy-5-oxopentanoic acidA
4-amino-3,5,6-trihydroxyhexanoic acid
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidD wrong
OHC
OHOH
NH2OH
O
B
4-amino-3,5-dihydroxy-5-oxopentanoic acidA
4-amino-3,5,6-trihydroxyhexanoic acid
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidD wrong
OHC
OHOH
NH2OH
OThere are only two alcohol/
hydroxy groups. This OH is part of the acid (all bonds to one C).
B
4-amino-3,5-dihydroxy-5-oxopentanoic acidA
4-amino-3,5,6-trihydroxyhexanoic acid
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidD wrong
OHC
OHOH
NH2OH
OThis is not an alcohol OH because of the position of the C. The C needs four bonds so
must have C=O
B
4-amino-3,5-dihydroxy-5-oxopentanoic acidA
4-amino-3,5,6-trihydroxyhexanoic acid
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidD wrong
OHC
OHOH
NH2OH
OThis is not an alcohol OH because of the position of the C. The C needs four bonds so
must have C=O
An alcohol would be HOH2C-
A
B
C
D
4-amino-3,5-dihydroxy-5-oxopentanoic acid
4-amino-3,5,6-trihydroxyhexanoic acid
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid
wrong
OHC
OHOH
NH2OH
O
A
B
C
D
4-amino-3,5-dihydroxy-5-oxopentanoic acid
4-amino-3,5,6-trihydroxyhexanoic acid
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid
wrong
OHC
OHOH
NH2OH
O
Major functional group controls the numbering,
so the acid is 1.
4-amino-3,5-dihydroxy-5-oxopentanoic acidA
4-amino-3,5,6-trihydroxyhexanoic acidB
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acidC
4-amino-3,5-dihydroxy-6-oxohexanoic acidD
OHC
OHOH
NH2OH
O
3example
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
NH2
OH
O
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
NH2
OH
O
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
NH2
OH
O
...or phenylalanine for those of you of a more biological disposition...
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acidwrong
NH2
OH
O
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acidwrong
NH2
OH
O
Major functional group controls the numbering, so the acid is 1 and not
the phenyl group
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
wrongNH2
OH
O
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
wrongNH2
OH
O
Both the carbonyl group and the hydroxyl are attached to the same carbon so they are the same
functional group (a carboxylic acid)
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
wrong
NH2
OH
O
A
B
C
D
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid
wrong
NH2
OH
O
The benzene ring can be considered as a functional group with the name phenyl (if it has 1 substituent) or benzene (if it has more than 1
substituent). It should not be called cyclohexa-1,3,5-triene or any variant.
4example
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamide
O NH2
OH
O2N
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamidewrong
O NH2
OH
O2N
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamidewrong
O NH2
OH
O2N
Most of this name is wrong. The amide takes priority and is the
suffix (benzamide). If the OH took priority it would be a phenol.
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamidewrong
O NH2
OH
O2N
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamidewrong
O NH2
OH
O2N
Amide still takes priority so it is not a phenol
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamide
wrong
O NH2
OH
O2N
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamide
wrong
O NH2
OH
O2N
Both the C=O and the C–N are the same carbon so this is one functional group. It is an amide not an aldehyde and an amine.
A
B
C
D
2-carbamoyl-4-nitrobenzenol
2-carbamoyl-4-nitrophenol
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamide
O NH2
OH
O2N
draw the molecule with the following name...
4-ethyl-3-hydroxycyclohexanone
4-ethyl-3-hydroxycyclohexanone
1parent
O
4-ethyl-3-hydroxycyclohexanone
2suffix
O
4-ethyl-3-hydroxycyclohexanone
4prefix
O
H3C
O
4-ethyl-3-hydroxycyclohexanone
4prefix
O
H3C
numbering starts from major functional
group
12
34
O
H3C
OH
O
4-ethyl-3-hydroxycyclohexanone
4functional groups
12
3
4
2example
2-hydroxy-3,3-dimethylpentanoic acid
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
Hydroxyl group in wrong position. Numbering starts with the major
functional group, thecarboxylic acid
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
The carbon chain is too short (pent = 5)
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
CO2H
OH
CO2H
OH
CO2H
OH OHOHO
A B
C D
2-hydroxy-3,3-dimethylpentanoic acid
✔✗
✗ ✗
No carboxylic acid present. Instead we have erroneously
have an aldehyde and an alcohol.
3example
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗This is not a carboxylic
acid. Instead it has both an aldehyde and an
alcohol. Carboxylic acids have the C=O and the OH
on the same carbon atom.
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗Bromo is part of the prefix so is attached
directly to the benzene ring
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗Bromo is part of the prefix so is attached
directly to the benzene ring
If it was attached to the methyl group then it would be grouped with the
methyl (e.g. 3-(bromomethyl)benzoic acid)
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗Numbering is wrong. Carboxylic acid takes priority so the numbering within the ring starts from the carbon attached to the acid. The
drawing shows 2-bromo-5-methylbenzoic acid.
3-bromo-5-methylbenzoic acid
O OH
Br
O OH
Br
O OH
Br
O
BrHO
A B
C D
✔
✗
✗
✗
functional groups
these are listed on pg 17
Read functional groups (Pg16-29)
©hebedesign@flickr
I will not have time to go through these
HC
HHH
methaneCH4
alkanes
CnH2n+2
propaneC3H8
HC
HHH
methaneCH4
alkanes
CnH2n+2
propaneC3H8open chains (no
rings) have this general formula
CnH2n+2
Reference
C6H2x6+2
H
H H
H H
H H
H H
H HH
H H
C6H14
CnH2n+2
Functional groups
C6H12 ≠ CnH2n+2
CnH2n+2
Functional groups
C6H12 ≠ CnH2n+2if a molecule does not agree with this
formula, it has either a ring or functional group (look at double bond equivalence (dbe)
if you are interested).
HC
HHH
methaneCH4
alkanes
CnH2n+2
propaneC3H8
alkanes are tetrahedral in
shape...we shall see why later
HC
HHH
methaneCH4
alkanes
CnH2n+2
propaneC3H8
alkanes are boring...normally fuels or solvents
2,2-dimethylpropane
C5H12bp 9.6˚C
2-methylbutaneC5H12
bp 28˚C
pentaneC5H12
bp 36.2˚C
structuralisomers
2,2-dimethylpropane
C5H12bp 9.6˚C
2-methylbutaneC5H12
bp 28˚C
pentaneC5H12
bp 36.2˚C
structuralisomers
same number of atoms – but bonding
different
2,2-dimethylpropane
C5H12bp 9.6˚C
2-methylbutaneC5H12
bp 28˚C
pentaneC5H12
bp 36.2˚C
structuralisomers
can make big differences in properties...as
we shall see later
alkenes
trigonal planarH
H H
Hethene
alkenes
trigonal planarH
H H
Hethene
more exciting as the double bond is
reactive!
alkenes
trigonal planarH
H H
Hethene
means it is flat with three groups
attached to central atom
trans-2-buteneC4H8
H3C
CH3H3C CH3
cis-2-buteneC4H8
1-buteneC4H8
2-methylpropeneC4H8
cyclobutaneC4H8
configurational (stereoisomers)
isomers
no rotation around C=C bond
trans-2-buteneC4H8
H3C
CH3H3C CH3
cis-2-buteneC4H8
1-buteneC4H8
2-methylpropeneC4H8
cyclobutaneC4H8
configurational (stereoisomers)
isomers
no rotation around C=C bond
these 2 are structural isomers
trans-2-buteneC4H8
H3C
CH3H3C CH3
cis-2-buteneC4H8
1-buteneC4H8
2-methylpropeneC4H8
cyclobutaneC4H8
configurational (stereoisomers)
isomers
no rotation around C=C bond
these 2 are stereoisomers. Same atoms and bonds but different orientation in
space
trans-2-buteneC4H8
H3C
CH3H3C CH3
cis-2-buteneC4H8
1-buteneC4H8
2-methylpropeneC4H8
cyclobutaneC4H8
configurational (stereoisomers)
isomers
no rotation around C=C bond
occurs becomes alkene cannot
rotate
trans-2-buteneC4H8
H3C
CH3H3C CH3
cis-2-buteneC4H8
1-buteneC4H8
2-methylpropeneC4H8
cyclobutaneC4H8
configurational (stereoisomers)
isomers
no rotation around C=C bond
a whole world of pain is coming your way when we discuss stereoisomers!
alkenes in nature
CH3H3C
H3C
CH3CH3H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-eneα-pinene
alkenes in nature
CH3H3C
H3C
CH3CH3H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-eneα-pinene
yup...it smells of pine...and is a very useful compound in
chemistry
alkynes
O
O
O
O
OO
O
H3C
OMe
OH
OOH
HO
CH3
MeHN
neocarzinostatin chromophore A
H HethyneC2H2
triple bond makes alkynes long
cylinders
alkynes
O
O
O
O
OO
O
H3C
OMe
OH
OOH
HO
CH3
MeHN
neocarzinostatin chromophore A
H HethyneC2H2
they are found in nature...this nasty beast cleaves DNA
cyclohexaneC6H12
cyclic compounds
benzeneC6H6
cyclohexaneC6H12
cyclic compounds
benzeneC6H6
some cyclic molecules are
flat...because they have flat double
bonds
cyclohexaneC6H12
cyclic compounds
benzeneC6H6
some look flat flat...but are not due to tetrahedral alkane structure (see lct 7)
cyclic structures in 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]phenanthrenecholestane - steroid
alcohols
OHethanolC2H6O
alcohols
OHethanolC2H6O
need OH attached to alkane (not alkene, alkyne or benzene)
alcohols
OHethanolC2H6O
found in many biological systems...
alcohols
OHethanolC2H6O
...especially on Saturday nights...
HOOH
1,2-ethandiolethylene glycol
antifreeze
alcohols in the real world
or Sunday mornings...O
HOHO
HO
HOOH
6-(hydroxymethyl)-tetrahydro-2H-pyran-2,3,4,5-tetraol
glucosesugar I guess!
H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-olcitronellol
citronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterolall animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-oltea tree oil
three classes of alcohol
tertiary (3°)
secondary (2°)
primary (1°)
H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-olcitronellol
citronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterolall animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-oltea tree oil
three classes of alcohol
tertiary (3°)
secondary (2°)
primary (1°)
depends on the number of carbons
attached to theC–OH unit
H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-olcitronellol
citronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterolall animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-oltea tree oil
three classes of alcohol
tertiary (3°)
secondary (2°)
primary (1°)
...this one has 1 carbon attached so is
primary. the next has 2 so is
secondary etc.
H3C OH
CH3 CH3
(R)-3,7-dimethyloct-6-en-1-olcitronellol
citronella oil
CH3
CH3
H3C
H3C
CH3
H H
H
HOcholesterolall animals
CH3
OHH3C
CH3(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-oltea tree oil
three classes of alcohol
tertiary (3°)
secondary (2°)
primary (1°)
this controls the reactivity of the alcohols as you
shall see in future lectures
important terms & common mistakes
X
HH
X
H
X
primarygroup
secondarygroup
tertiarygroup
not just true of alcohols but all
functional groups
phenolsOH
phenolcarbolic acid
HO
OH3C
HN
O
CH3
H3C
(E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
capsaicinchilli peppers
phenolsOH
phenolcarbolic acid
HO
OH3C
HN
O
CH3
H3C
(E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
capsaicinchilli peppers
looks like an alcohol BUT is not
(as it is not attached to an
alkane)
phenolsOH
phenolcarbolic acid
HO
OH3C
HN
O
CH3
H3C
(E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
capsaicinchilli peppers
thus has very different
properties...I should whistle ‘ring of fire’
now...
important terms & common mistakes
R
OH
RR
alcohol(R = C or H)
OH
phenol1 million times
more acidic than an aliphatic alcohol
OH
enolyou can
ignore this one
ethers
H3C O CH3
ethoxyethanediethyl ether
ether
O
tetrahydrofuranTHF
OO
OO
O
O
18-crown-6replace one carbon
in an alkyl chain and you have an ether.
Often used as solvents
18-crown-6 and potassium cation
halidesH
HClCl
dichloromethaneDCM
F
FClCl
dichlorodifluoromethaneFreon (refrigerant)
a CFCClCl
Cl
ClCl
Cl HH
O
dieldrin
Pic: NASA
organic molecules containing fluorine, chlorine, bromine or
iodine
halidesH
HClCl
dichloromethaneDCM
F
FClCl
dichlorodifluoromethaneFreon (refrigerant)
a CFCClCl
Cl
ClCl
Cl HH
O
dieldrin
Pic: NASA
often toxic and some are responsible for
the hole in the ozone layer
thiols
H3C CH3 H3C CH3
HS SH OCH3HS
propane-2,2-dithiol 4-methyl-4-sulfanylpentan-2-one
H2N
SH
HCO2H
(R)-2-amino-3-sulfanylpropanoic acid
cysteine these are the sulfur version of
alcohols...found in nature (and us)
thiols
H3C CH3 H3C CH3
HS SH OCH3HS
propane-2,2-dithiol 4-methyl-4-sulfanylpentan-2-one
H2N
SH
HCO2H
(R)-2-amino-3-sulfanylpropanoic acid
cysteineone of these is the smelliest chemical
known...but no one wants to repeat the experiment
to find out which!
CH3
H3C
CH3HS
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 taste
of grapefruit!
CH3
H3C
CH3HS
2-(4-methylcyclohex-3-enyl)propane-2-thioltaste of grapefruit
2x10-5 ppbthis value is similar to
1 drop in a lake...
aminesCH3
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).
amines in nature
H2N HOH
O
(S)-2-amino-3-phenylpropanoic acid
phenylalanineamino acid
H3C OH
CH3 O
NH2
(S)-2-amino-3-methylbutanoic acid
valineamino acid
amino acids are an obvious source of
amines
amines in nature
O
O
O
OCH3
NCH3
methyl 3-(benzoyloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-
carboxylatecocaine
Scarface (1983): Universal Pictures
amines in nature
O
O
O
OCH3
NCH3
methyl 3-(benzoyloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-
carboxylatecocaine
Scarface (1983): Universal Pictures
but there is a problem bigger than drugs...
five kinds of amine
NHH
Hammonia
H3C NH2
methylamine1° amine
H3CHN
CH3dimethylamine
2° amine
NCH3
H3CH3C
trimethylamine3° amine
NCH3
H3CH3C
trimethylammonium ion4° ammonium (salt)
H
five kinds of amine
NHH
Hammonia
H3C NH2
methylamine1° amine
H3CHN
CH3dimethylamine
2° amine
NCH3
H3CH3C
trimethylamine3° amine
NCH3
H3CH3C
trimethylammonium ion4° ammonium (salt)
H but primary, secondary & tertiary
mean something different than when we used them with
alcohols!
five kinds of amine
NHH
Hammonia
H3C NH2
methylamine1° amine
H3CHN
CH3dimethylamine
2° amine
NCH3
H3CH3C
trimethylamine3° amine
NCH3
H3CH3C
trimethylammonium ion4° ammonium (salt)
H...now refer to the
number of C attached to the N...but it gets
worse...
the problem with amines
primary amine(1°)
secondary position(2°)
H3C OH
CH3 O
NH2
primary amine because only 1 carbon attached
the problem with amines
primary amine(1°)
secondary position(2°)
H3C OH
CH3 O
NH2
but in a secondary position (like alcohol
naming) as this carbon has 2 carbons
attached!
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: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
C=O is the cornerstone of organic synthesis.
Aldehydes = CHO and are more reactive than...
carbonyl:ketones
H3C CH3
O
propanoneacetone
CH3
H
O
H3C
(R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
(R)-carvonespearmint
CH3
H
O
CH3
(S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
(S)-carvonecaraway
carbonyl:ketones
H3C CH3
O
propanoneacetone
CH3
H
O
H3C
(R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
(R)-carvonespearmint
CH3
H
O
CH3
(S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
(S)-carvonecaraway
ketones, which have C=O bonded to two
carbon groups
carboxylic acid derivatives: acids
H3C OH
O
ethanoic acidacetic acid
vinegar
H3CO
OHOH
(S)-2-hydroxy-propanoic acidL-(+)-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 acid
abscisic acidleaf fallC=O bonded to 1
carbon and an OH group
carboxylic acid derivatives: others
H3C O
ONa
sodium ethanoatecarboxylate ion
H3CO
CH3
O
CH32-methylpropyl propanoate
isobutyl propionatesmell of rum
ester
HO2CHN
OMe
NH2
O
O
aspartamesweetener
amide
many different derivatives
depending on what is attached to C=O
important terms & common mistakes
atoms attached to the same carbon count as one functional group
OH
RR
alcoholR = C or H
O
aldehyde
O
OHNOT
an aldehyde+
an alcohol
O
OHcarboxylic
acid
atoms attached to the same carbon count as one functional group
important terms & common mistakes
NH2
RR
amineR = C or H
O
aldehyde
O
NH2
NOTan aldehyde
+an amine
O
NH2
amide
OHC-R ≠ HOC-R
OC
H R≠ O
CR
H
This actually meaningless as the C does not have 4 bonds
important terms & common mistakes
Learn to draw accurately
how are functional groups related?
R CH
HH
hydrocarbon
R COH
HH R C
O
HR C
O
OH
alcohol aldehyde carboxylicacid
oxidation
reduction
oxidation
reduction
oxidation
reduction
alkanes
alcoholsethersamineshalidesthiols
aldehydesketones
carboxylic acidsestersamides
acyl halidesacid anhydrides
nitriles
Read this unit againLearn the functional groups
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NH
HN
HN
NH
HN
NH
NHMe
Me
Me
OO
O
O
O
HO OHOH
O O
O
NH2
OHHO
O
Cl
Cl
O
HOHO
OH
OOMe
NH2OH
Me
HO2CO
Vancomycin
what have....we learnt? •naming (simple)
molecules•recognise functional groups
molecules may look complicated but simply break them down into their functional groups
(amides in red)
parts 3 & 4are combined
word of warning...next 2
units will not be in the same order as
study guide...
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readPages 35, 37, 41-42, 45-47