The document provides information on naming organic molecules, including the steps and rules for assigning IUPAC names. It explains that molecules are named using a systematic approach with four main components: 1. The parent chain, which is the longest continuous carbon chain containing the functional group. 2. The suffix for the major functional group, which is given the lowest possible number. 3. Prefixes indicating any substituents or minor functional groups, listed in alphabetical order with their position numbers. 4. The order of the name, which follows alphabetical order except for descriptors like tert which are ignored. Examples are provided to illustrate the naming process.

1. Unit One Part 2:
naming & functional groups
H3C O CH3
N H
N O
N
N
H3C S O
N
O
N
H3C
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

2. Unit One Part 2:
naming & functional groups
H3C O CH3
N H
N O
N
N
H3C S O
N
O
N
H3C
viagra™ (trade name)
sildenafil (trivial name) panic!
Don’t
5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1-
We won’t do anything
methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
this complicated

3. Unit One
2
Part molecules (pg 11-16)
Naming
Introducing functional
groups (pg 16-9)
remember...read the
study guide it
contains all you need

4. how do we
name molecules?

5. O
OH
NH2
2-amino-4-methylpentanoic acid
prefix parent suffix
substituents carbon chain principal
minor functional (& multiple functional
groups bonds) groups

6. O
OH
NH2
2-amino-4-methylpentanoic acid
there are three parts
to any name...even
Viagra’s real name
prefix parent suffix
obeys this.
substituents carbon chain principal
minor functional (& multiple functional
groups bonds) groups

7. O
OH
NH2
2-amino-4-methylpentanoic acid
the prefix can
become a nightmare
as it contains most
information
prefix parent suffix
substituents carbon chain principal
minor functional (& multiple functional
groups bonds) groups

8. five steps to
success!

9. five steps to
success!
works for all
molecules but the
whole system takes
volumes to
explain...

10. 1
parent
longest carbon
chain containing a
functional group page 12/13 of guide
CH3 CH3
OH
H3C CH3 H3C 4 2
5 3 1
4-methylheptane 2-propyl-1-pentanol

11. 1
parent
longest carbon
chain containing a
functional group
CH3 7 bigger than 5 he
CH3
says patronisingly
OH
H3C CH3 H3C 4 2
5 3 1
4-methylheptane 2-propyl-1-pentanol

12. 1
parent
longest carbon
chain containing a
functional group
CH3 CH3
now use pent- as OH
H3C we have to start 3
CH H3C 4 2
5 3 1
our chain from the
4-methylheptane
functional group 2-propyl-1-pentanol

13. 2
suffix
major
functional
group
list of major
groups pg 13
order of priority
pg 14
O CH3 O
H3C OH H3C NH2
butanoic acid 3-methylbutanamide

14. 2
suffix
major
functional
group
O CH3 O
H3C OH H3C NH2
butanoic acid 3-methylbutanamide
only one major
group per
molecule

15. 2
minor FG
not all groups are
equal: halo- & nitro-
a (-NO2) are prefixes
H3C O
Br N
CH3 O
1-bromo-2-methylpropane nitroethane
no idea why!
But please remember they
are functional groups. It is
only for naming that they
do not count

16. 3
position
of functional
group from number longest
end of chain chain (parent)
from start to
finish...
O
HO
H3C CH3
O
2-pentanone 5-methylheptanoic acid
pentan-2-one
NOT 4-pentanone

17. 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

18. 3
position
of functional
group from
end of chain
it doesn’t matter
O where number
HO goes but I think the
second example
H3C CH3
avoids confusion
O later
2-pentanone 5-methylheptanoic acid
pentan-2-one
NOT 4-pentanone

19. 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

20. 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 slide)
CH3
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane

21. 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

22. 4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
H3C CH3 note: group identical
H3C substituentsCH3
(or
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

23. 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

24. 4
prefix
substituents
(and minor
functional
groups)
CH3 Cl CH3
bizarrely, 3C
H halides don’t CH3
count as functional H3C CH3
groups...don’t ask...
H3C CH3 CH3
2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane
NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane

25. 4
Prefix
contains everything except
major functional group
and multiple bonds
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
multiple bonds combined with parent

26. 4
Prefix
contains everything except
major functional group
and multiple bonds
functional groups
listed on pg 13
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
multiple bonds combined with parent

27. 4
Prefix
contains everything except
major functional group
and multiple bonds
O O CH3
major functional
group is suffix and is
H3C 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
multiple bonds combined with parent

28. 4
Prefix
contains everything except
major functional group
and multiple bonds
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
multiple bonds combined with parent

29. 4
Prefix
contains everything except
major functional group
and multiple bonds alkenes and
alkynes are
normally part of
the parent
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
multiple bonds combined with parent

30. 5
order
a, b, c...hope
you know prefixes are ordered
alphabetically
your alphabet! (although descriptors
like tert are ignored)
NH
HO OH
O
3-hydroxy-2-(methylamino)pentanoic acid
NOT 2-(methylamino)-3-hydroxypentanoic
acid

31. name this
molecule...

32. OH O
H3C N CH3
H
hept
1
parent

33. OH O
H3C N CH3
H
select longest
carbon chain (with
major functional
1
group in it)
parent

34. OH O
H3C N CH3
H
amide
2
suffix
hept
identify major
functional group –
this will be the
suffix

35. 6 OH O
H3C 5 3 1 N CH3
4 2 H
number chain
starting with major
3
functional group
hept amide
position

36. 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)

37. 6 OH O
H3C 5 3 N1 CH3
4 2 H
3-hydroxy 6-en
repeat with all
remaining
4
functional groups
hept amide 5-methyl
functional groups

38. 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
4
the rest
hept amide 5-methyl 3-hydroxy 6-en

39. OH O
H3C N CH3
H
N-ethyl-3-hydroxy-5-methylhept-6-enamide
5
order

40. OH O
H3C N CH3
H
N-ethyl-3-hydroxy-5-methylhept-6-enamide
to be honest order
5
not too important
as long as name is
not ambiguous
order

41. N-ethyl?
(methylamino)?

42. what the
©Renaissance Pictures
@&!!#?

43. DON’T
PANIC !
only simple examples in test

44. On the next slide there
is a skeletal structure and
four possible names.
2
Which is correct?
example

45. NH2
OHC OH
OH OH O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
B 4-amino-3,5,6-trihydroxyhexanoic acid
C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
D 4-amino-3,5-dihydroxy-6-oxohexanoic acid

46. NH2
OHC OH
OH OH O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
rong
B 4-amino-3,5,6-trihydroxyhexanoic acid
C
D
w
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid

47. NH2
OHC OH
OH OH O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
The parent contains 6 C.
rong
B 4-amino-3,5,6-trihydroxyhexanoic acid
The carbon C of CHO still
w
counts!
C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
D 4-amino-3,5-dihydroxy-6-oxohexanoic acid

48. NH2
OHC OH
OH OH O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
B 4-amino-3,5,6-trihydroxyhexanoic acid
C
D wrong
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid

49. NH2
OHC OH
There are only two alcohol/
hydroxy groups. This OH is part
of the acid (all bonds to one C).
OH OH O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
B 4-amino-3,5,6-trihydroxyhexanoic acid
C
D wrong
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid

50. NH2
OHC OH
OH OH
This is not an alcohol OH
because of the position of the
O
C. The C needs four bonds so
must have C=O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
B 4-amino-3,5,6-trihydroxyhexanoic acid
C
D wrong
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid

51. NH2
OHC OH
OH OH
This is not an alcohol OH
because of the position of the
O An alcohol
C. The C needs four bonds so would be
must have C=O HOH2C-
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
B 4-amino-3,5,6-trihydroxyhexanoic acid
C
D wrong
3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
4-amino-3,5-dihydroxy-6-oxohexanoic acid

52. NH2
OHC OH
OH OH O
A
B wrong
4-amino-3,5-dihydroxy-5-oxopentanoic acid
4-amino-3,5,6-trihydroxyhexanoic acid
C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
D 4-amino-3,5-dihydroxy-6-oxohexanoic acid

53. NH2
OHC OH
OH OH O
A
B wrong
4-amino-3,5-dihydroxy-5-oxopentanoic acid
Major functional group
4-amino-3,5,6-trihydroxyhexanoic acid
controls the numbering,
so the acid is 1.
C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
D 4-amino-3,5-dihydroxy-6-oxohexanoic acid

54. NH2
OHC OH
OH OH O
A 4-amino-3,5-dihydroxy-5-oxopentanoic acid
B 4-amino-3,5,6-trihydroxyhexanoic acid
C 3-amino-2,4-dihydroxy-1-oxo-6-hexanoic acid
D 4-amino-3,5-dihydroxy-6-oxohexanoic acid

55. example
3

56. O
OH
NH2
A 2-amino-3-phenylpropanoic acid
B 2-amino-1-phenylpropanoic acid
C 2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

57. O
OH
NH2
A 2-amino-3-phenylpropanoic acid
B 2-amino-1-phenylpropanoic acid
C 2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

58. O
OH
NH2
A 2-amino-3-phenylpropanoic acid
B 2-amino-1-phenylpropanoic acid
...or phenylalanine for
those of you of a more
biological disposition...
C 2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

59. O
OH
NH2
A 2-amino-3-phenylpropanoic acid
B 2-amino-1-phenylpropanoic acid
C
D wrong
2-amino-1-hydroxy-3-phenylpropanone
2-amino-nona-4,6,8-trienoic acid

60. O
OH
NH2
A 2-amino-3-phenylpropanoic acid
B 2-amino-1-phenylpropanoic acid
C
wrong
2-amino-1-hydroxy-3-phenylpropanone
Major functional group
controls the numbering,
so the acid is 1 and not
D 2-amino-nona-4,6,8-trienoic acid
the phenyl group

61. O
OH
NH2
A
B wrong
2-amino-3-phenylpropanoic acid
2-amino-1-phenylpropanoic acid
C 2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

62. O
OH
NH2
Both the carbonyl group and the hydroxyl are
attached to the same carbon so they are the same
rong
functional group (a carboxylic acid)
w
A 2-amino-3-phenylpropanoic acid
B 2-amino-1-phenylpropanoic acid
C 2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

63. O
OH
NH2
A 2-amino-3-phenylpropanoic acid
B
C
wrong
2-amino-1-phenylpropanoic acid
2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

64. O
OH
NH2
The benzene ring can be considered as a
A 2-amino-3-phenylpropanoic acid
ong
functional group with the name phenyl (if it has
wr
1 substituent) or benzene (if it has more than 1
substituent). It should not be called
B 2-amino-1-phenylpropanoic acid
cyclohexa-1,3,5-triene or any variant.
C 2-amino-1-hydroxy-3-phenylpropanone
D 2-amino-nona-4,6,8-trienoic acid

65. example
4

66. O NH2
OH
O2N
A 2-carbamoyl-4-nitrobenzenol
B 2-carbamoyl-4-nitrophenol
C 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
D 2-hydroxy-5-nitrobenzamide

67. O NH2
OH
O2N
A 2-carbamoyl-4-nitrobenzenol
ong
B 2-carbamoyl-4-nitrophenol
C
D
wr
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
2-hydroxy-5-nitrobenzamide

68. O NH2
OH
O2N
A 2-carbamoyl-4-nitrobenzenol
ong
B 2-carbamoyl-4-nitrophenol
C
D
wr
1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
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.
2-hydroxy-5-nitrobenzamide

69. O NH2
OH
O2N
A 2-carbamoyl-4-nitrobenzenol
B 2-carbamoyl-4-nitrophenol
wrong
C 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
D 2-hydroxy-5-nitrobenzamide

70. O NH2
OH
O2N
A 2-carbamoyl-4-nitrobenzenol
B 2-carbamoyl-4-nitrophenol
wrong
C 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
Amide still takes priority so it is
not a phenol
D 2-hydroxy-5-nitrobenzamide

71. O NH2
OH
O2N
wrong
A 2-carbamoyl-4-nitrobenzenol
B 2-carbamoyl-4-nitrophenol
C 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
D 2-hydroxy-5-nitrobenzamide

72. O NH2
OH
O2N
wrong
A 2-carbamoyl-4-nitrobenzenol
B 2-carbamoyl-4-nitrophenol
C 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
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.
D 2-hydroxy-5-nitrobenzamide

73. O NH2
OH
O2N
A 2-carbamoyl-4-nitrobenzenol
B 2-carbamoyl-4-nitrophenol
C 1-(aminomethyl)-2-hydroxy-5-nitrobenzaldehyde
D 2-hydroxy-5-nitrobenzamide

74. draw the molecule
with the following
name...

75. 4-ethyl-3-hydroxycyclohexanone

76. 4-ethyl-3-hydroxycyclohexanone
1 parent

77. 4-ethyl-3-hydroxycyclohexanone
O
2 suffix

78. 4-ethyl-3-hydroxycyclohexanone
O
4
H3C
prefix

79. 4-ethyl-3-hydroxycyclohexanone
numbering starts
from major functional
group
O
1
2
3
4
4
H3C
prefix

80. 4-ethyl-3-hydroxycyclohexanone
O
1
2
3
4 OH
4
H3C
functional groups

81. example
2

82. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
A B
OH OH
O OH
CO2H
C D

83. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
✗
A
OH
✔B
OH
O OH
CO2H
✗
C
✗
D

84. 2-hydroxy-3,3-dimethylpentanoic acid
Hydroxyl group in wrong position.
Numbering starts with the major
functional group, the
OH OH
carboxylic acid
CO2H CO2H
✗
A
OH
✔ B
OH
O OH
CO2H
✗
C
✗D

85. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
✗
A
OH
✔B
OH
O OH
CO2H
✗
C
✗
D

86. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
✗
A
OH
✔B
OH
O OH
CO2H
✗
C
✗
D

87. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
✗
A
OH
✔ B
The carbon chain is
OH
too short (pent = 5)
O OH
CO2H
✗
C
✗D

88. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
✗
A
OH
✔B
OH
O OH
CO2H
✗
C
✗
D

89. 2-hydroxy-3,3-dimethylpentanoic acid
OH OH
CO2H CO2H
✗ ✔
No carboxylic acid present.
Instead we have erroneously
A have an aldehyde and an
alcohol.
B
OH OH
O OH
CO2H
✗
C
✗
D

90. example
3

91. 3-bromo-5-methylbenzoic acid
O O OH
HO Br
Br
A B
O OH O OH
Br
Br
C D

92. 3-bromo-5-methylbenzoic acid
O O OH
HO ✗
A
Br
Br ✗
B
O OH O OH
✗
Br
✔ Br
C D

93. 3-bromo-5-methylbenzoic acid
O O OH
✗ ✗
This is not a carboxylic
acid. Instead it has both
an aldehyde and an
alcohol. Carboxylic acids
HO Br have the C=O and the OH
Br on the same carbon
A B atom.
O OH O OH
✗
Br
✔Br
C D

94. 3-bromo-5-methylbenzoic acid
O O OH
HO ✗
A
Br
Br ✗
B
O OH O OH
✗
Br
✔ Br
C D

95. 3-bromo-5-methylbenzoic acid
O O OH
HO
Bromo is part of the
prefix so is attached
✗
A
Br
Br ✗
B
directly to the benzene
ring O OH O OH
✗
Br
✔ Br
C D

96. 3-bromo-5-methylbenzoic acid
O O OH
HO
Bromo is part of the
prefix so is attached
✗
A
Br
Br ✗
If it was attached to the methyl group
B
then it would be grouped with the
directly to the benzene
ring O OH O OH
methyl (e.g. 3-(bromomethyl)benzoic
acid)
✗
Br
✔Br
C D

97. 3-bromo-5-methylbenzoic acid
O O OH
HO ✗
A
Br
Br ✗
B
O OH O OH
✗
Br
✔ Br
C D

98. 3-bromo-5-methylbenzoic acid
O O OH
HO ✗
A
Br
Br ✗
Numbering is wrong.
Carboxylic acid takes priority
so the numbering within the
ring starts from the carbon
B
attached to the acid. The
drawing shows 2-bromo-5-
O OH O OH
methylbenzoic acid.
✗
Br
✔Br
C D

99. 3-bromo-5-methylbenzoic acid
O O OH
HO ✗
A
Br
Br ✗
B
O OH O OH
✗
Br
✔ Br
C D

100. functional groups
these are listed on
pg 17

101. Read functional
groups (Pg16-29)
©hebedesign@flickr
I will not have time to go through these

102. alkanes
H
H C H
H
methane
CH4
propane
C3H8
CnH2n+2

103. alkanes
H
H C H
H
methane
CH4
propane
open chains (no C3H8
rings) have this
general formula
CnH2n+2

104. CnH2n+2
C6H2x6+2
H H H H H H
H C6H14
H
H H H H H H
Reference

105. CnH2n+2
C6H12 ≠ CnH2n+2
Functional groups

106. CnH2n+2
C6H12 ≠ CnH2n+2
if 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).
Functional groups

107. alkanes
H
H C H
H
methane
CH4
alkanes are
tetrahedral in
shape...we shall see
why later
propane
C3H8
CnH2n+2

108. alkanes
H
H C H
H
methane
CH4
alkanes are
boring...normally
fuels or solvents
propane
C3H8
CnH2n+2

109. structural
isomers
pentane 2-methylbutane 2,2-dimethyl
C5H12 C5H12 propane
bp 36.2˚C bp 28˚C C5H12
bp 9.6˚C

110. structural
isomers
same number of
atoms – but bonding
different
pentane 2-methylbutane 2,2-dimethyl
C5H12 C5H12 propane
bp 36.2˚C bp 28˚C C5H12
bp 9.6˚C

111. structural
isomers
can make big
pentane 2-methylbutane
differences in
2,2-dimethyl
C5H12 C5H12 properties...as propane
bp 36.2˚C bp 28˚C shall see later
we C5H12
bp 9.6˚C

112. alkenes
H H
H H
ethene
trigonal planar

113. alkenes
more exciting as the
double bond is
reactive! H H
H H
ethene
trigonal planar

114. alkenes
means it is flat with
three groups
attached to central
atom
H H
H H
ethene
trigonal planar

115. configurational
(stereoisomers)
isomers
1-butene 2-methylpropene cyclobutane
C4H8 C4H8 C4H8
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
no rotation around C=C bond

116. configurational
(stereoisomers)
isomers
these 2 are structural
isomers
1-butene 2-methylpropene cyclobutane
C4H8 C4H8 C4H8
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
no rotation around C=C bond

117. configurational
(stereoisomers)
isomers
these 2 are
stereoisomers. Same
1-butene and bonds but
atoms 2-methylpropene cyclobutane
C4different orientation in
H8 C4H8 C4H8
space
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
no rotation around C=C bond

118. configurational
(stereoisomers)
isomers
1-butene 2-methylpropene cyclobutane
occurs becomes
C4H8 C4H8 alkene cannot C4H8
rotate
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
no rotation around C=C bond

119. configurational
(stereoisomers)
isomers
a whole world of pain
1-butene
is coming your way 2-methylpropene cyclobutane
C4H8when we discuss C4H8 C4H8
stereoisomers!
CH3
H3C CH3
H3C
trans-2-butene cis-2-butene
C4H8 C4H8
no rotation around C=C bond

120. alkenes
in nature
H3C CH3
CH3
H3C
CH3
H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
α-pinene

121. 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

122. 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

123. 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

124. cyclic compounds
cyclohexane benzene
C6H12 C6H6

125. cyclic compounds
some cyclic
molecules are
flat...because they
have flat double
bonds
cyclohexane benzene
C6H12 C6H6

126. cyclic compounds
some look flat
flat...but are not due
to tetrahedral alkane
structure (see lct 7)
cyclohexane benzene
C6H12 C6H6

127. 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

128. alcohols
OH
ethanol
C2H6O

129. alcohols
need OH attached to
alkane (not alkene,
alkyne or benzene)
OH
ethanol
C2H6O

130. alcohols
found in many
biological systems...
OH
ethanol
C2H6O

131. alcohols ...especially on
Saturday nights...
OH
ethanol
C2H6O

132. alcohols in
the real world
HO
or Sunday HO
HO O 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!

133. 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

134. 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
depends on the tertiary (3°)
number of carbons3C
H OH
attached to the
C–OH unit CH3
(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil

135. three classes
of alcohol H3C
CH3
CH3 CH3
secondary (2°)
...this one has 1
CH3 H carbon attached so is
CH
primary. the next 3
H3C OH
has 2 so is
H H3C
H secondary etc.
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

136. 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
this controls the tertiary (3°)
reactivity of theH3C OH
alcohols as you
shall see in future CH3
lectures
(R)-1-isopropyl-4-methylcyclohex-3-enol
terpinen-4-ol
tea tree oil

137. important terms & not just true of
alcohols but all
common mistakes functional groups
X X X
H H
H
primary secondary tertiary
group group group

138. phenols
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

139. phenols looks like an
alcohol BUT is not
(as it is not
CH3
attached to an
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

140. 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

141. important terms &
common mistakes
OH
OH OH
R R
R
alcohol phenol enol
(R = C or H) 1 million times you can
more acidic than ignore this one
an aliphatic alcohol

142. 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

143. 18-crown-6
and potassium
cation

144. 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

145. 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

146. 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)

147. 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!

148. CH3
2x10-5 ppb
HS
H3C
CH3
2-(4-methylcyclohex-3-
enyl)propane-2-thiol
taste of grapefruit
can smell nice...garlic,
truffles etc...And incredibly
small amounts are the taste
of grapefruit!

149. CH3
2x10-5 ppb
HS
H3C
CH3
2-(4-methylcyclohex-3-
enyl)propane-2-thiol
taste of grapefruit value is similar to
this
1 drop in a lake...

150. 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
...also smell bad but
are vital for life (and
the smell of death).

151. amines in
nature
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
amino acids are an
obvious source of
amines

152. amines in nature N
CH3 O
CH3
O
O
O
methyl 3-(benzoyloxy)-8-methyl-
8-aza-bicyclo[3.2.1]octane-2-
carboxylate
cocaine
Scarface (1983): Universal Pictures

153. amines in nature N
CH3 O
CH3
O
O
O
methyl 3-(benzoyloxy)-8-methyl-
8-aza-bicyclo[3.2.1]octane-2-
carboxylate
cocaine
but there is a problem
bigger than drugs...
Scarface (1983): Universal Pictures

154. 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
H3C N CH
3
H3C
trimethylammonium ion
4° ammonium (salt)

155. 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)

156. 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)

157. the problem
with amines primary amine
because only 1
primary amine carbon attached
(1°)
NH2
H3C OH
CH3 O
secondary position
(2°)

158. the problem
with amines but in a secondary
primary amine (like alcohol
position
(1°)naming) as this carbon
has 2 carbons
attached!
NH2
H3C OH
CH3 O
secondary position
(2°)

159. carbonyl:
aldehydes O
O O
H
H H H3C H
methanal ethanal benzaldehyde
formaldehyde acetaldehyde
OH OH
O
HO
OH OH H
(2R,3S,4R,5R)-2,3,4,5,6-
pentahydroxyhexanal
glucose

160. carbonyl:
aldehydes O
O O
H
H H H3C H
methanal ethanal C=Obenzaldehyde
is the cornerstone
formaldehyde acetaldehyde of organic synthesis.
Aldehydes = CHO and
are more reactive than...
OH OH
O
HO
OH OH H
(2R,3S,4R,5R)-2,3,4,5,6-
pentahydroxyhexanal
glucose

161. carbonyl:
ketones
CH3 CH3
O O
O
H3C CH3
H3C H H CH3
(R)-2-methyl-5-(prop-1-en- propanone (S)-2-methyl-5-(prop-1-en-
2-yl)cyclohex-2-enone acetone 2-yl)cyclohex-2-enone
(R)-carvone (S)-carvone
spearmint caraway

162. carbonyl:
ketones
ketones, which have
CH3 C=O bonded to two
CH3
carbon groups
O O
O
H3C CH3
H3C H H CH3
(R)-2-methyl-5-(prop-1-en- propanone (S)-2-methyl-5-(prop-1-en-
2-yl)cyclohex-2-enone acetone 2-yl)cyclohex-2-enone
(R)-carvone (S)-carvone
spearmint caraway

163. carboxylic acid
derivatives: acids
H3C CH3 CH3
O
O
H3C
OH
H3C OH CO2H
OH O CH3
ethanoic acid (S)-2-hydroxy- (2Z,4E)-3-methyl-5-(2,6,6-
acetic acid propanoic acid trimethyl-4-oxocyclohex-2-
vinegar L-(+)-lactic acid enyl)penta-2,4-dienoic acid
abscisic acid
C=O bonded to 1 leaf fall
carbon and an OH
group

164. carboxylic acid
derivatives: others
O
O
H3C CH3
Na O
H3C O
CH3
sodium ethanoate 2-methylpropyl propanoate
carboxylate ion isobutyl propionate
smell of rum
ester
NH2 O
H
HO2C N many different
OMe derivatives
depending on what
O is attached to C=O
aspartame
sweetener
amide

165. important terms &
common mistakes
OH O O O
R
R OH OH
alcohol aldehyde NOT carboxylic
R = C or H an aldehyde acid
+
an alcohol
atoms attached to the same carbon
count as one functional group

166. important terms &
common mistakes
NH2 O O O
R
R NH2 NH2
amine aldehyde NOT amide
R = C or H an aldehyde
+
an amine
atoms attached to the same carbon
count as one functional group

167. important terms &
common mistakes
OHC-R ≠ HOC-R
O
≠ H C
C O R
H R
This actually meaningless as
Learn to draw the C does not have 4 bonds
accurately

168. how are functional
groups related?

169. 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

170. Read this unit again
Learn the functional groups ©sidewalk flying@flickr

171. 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
break them down into
their functional groups
OH (amides in red)
HO OH
Vancomycin

172. parts 3 & 4
are combined
word of
warning...next 2
units will not be in
the same order as
study guide...

173. read
Pages 35, 37,
41-42, 45-47
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