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LCT 2
LCT 2
H3C O CH3
N H
N O
N
N
H3C S O
N
O
N
H3C
Nomenclature rules
1. Parent - root derived from number of carbon in longest unbranched chain
.containing functional group
CH3 CH3
OH
H3C 4 2
H3C CH3 5 3 1
4-methylheptane 2-propyl-1-pentanol
2. Suffix - basic name derived by adding ending of major functional group (FG)
O CH3 O
H3C CH3
2-pentanone
pentan-2-one
NOT 4-pentanone
gjr-–- 5
Nomenclature rules II
4. Prefix - substituents are designated by prefix & Arabic number indicating
....position (lowest possible numbering)
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
5. FG - if more than one FG name & number based on principle FG. List of
....priorities given in course notes. Multiple bonds are added to parent (end),
....all others are prefixes
O O CH3
H3C OH
HO OH
H3C CH3 O
5-hydroxy-2,2-dimethylpentanoic acid 2-methyl-4-oxohex-2-enoic acid
6. Minor FG - halo-, nitro- (-NO2), nitroso- (-NO) & azo- (-N2-) are considered
....substituents & not FG for nomenclature only
Step 1: root
Step 7: complete
OH O OH O
OH O OH O
OH
H3C H3C
H C H
H
methane propane pentane cyclopentane
CH4 C3H8 C5H12 C5H10
CH4
isooctane
2,2,4-trimethylpentane
C8H18
H H
ethene
CH3
H3C CH3
H3C
1-butene 2-butenecis-2-butene
trans-2-butene 2-methylpropene cyclobutane
C4H8 C4H8 C4H8 C4H8
H3C CH3
CH3
H3C
CH3
H3C
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
α-pinene
gjr-–- 11
H H OH O
O
H3C OME
ethyne pent-3-yn-1-ol O O
C2H2 NOT pent-2-yn-5-ol
H3C O
OH O
MeHN
• Ethyne is an explosive gas HO
O
• Triple bond makes molecular linear (cylinder) OH
CH3
H3C CH3
cyclopropane 1,3-dimethylcyclohexane cyclohexene benzene
• Cyclic hydrocarbons are common - note that most are not flat
gjr-–- 12
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
H H
(R)-1-methyl-4-(prop-1-en-2- (S)-1-methyl-4-(prop-1-en-2-
yl)cyclohex-1-ene yl)cyclohex-1-ene
(R)-limonene (S)-limonene
smells of oranges smells of lemons
gjr-–- 13
HO O
OH HO
HO OH
HO
1,2-ethandiol 6-(hydroxymethyl)-tetrahydro-
ethylene glycol 2H-pyran-2,3,4,5-tetraol
antifreeze glucose
sugar I guess!
gjr-–- 14
Cl Cl
phenol 2,4,6-trichlorophenol
carbolic acid TCP
antiseptic
• Phenols are distinct from alcohols as attached to phenyl ring - acidic O–H
Ethers
O
O O
O
H3C O CH3
O O
ethoxyethane O
diethyl ether tetrahydrofuran
ether THF 18-crown-6
• Thiols are the sulfur analogue of alcohols - and they smell, bad...
• Humans can detect 2x10–5 ppb of the second compound (1 drop in a lake)
• One of the last two compounds is the smelliest known - but no one is
...prepared to make them again to find out which!
gjr-–- 16
H3C N NH2
H2N OH
H2N H
CH3
triethylamine butane-1,4-diamine (S)-2-amino-3-phenylpropanoic acid
smells of fish putrescine phenylalanine
smells of decay amino acid
CH3 O
N
CH3
O
N
H O
CH3
N
O
(S)-3-(1- methyl 3-(benzoyloxy)-8-methyl-
methylpyrrolidin-2-yl) 8-aza-bicyclo[3.2.1]octane-2-
pyridine carboxylate
nicotine cocaine
gjr-–- 17
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
primary
valine If add four groups
amine everything changes!
(1°)
gjr-–- 18
Ketones
CH3 CH3
O O
O
• Reaction of a carboxylic acid with a base (eg. NaOH) gives carboxylate ion
Derivatives
O O
O
H3C CH3
O Cl
H3C O CH3
CH3
ethyl ethanoate 2-methylpropyl propanoate benzoyl chloride
ethyl acetate isobutyl propionate acid chloride
solvent smell of rum
ester ester
NH2 O
H
HO2C N
OMe O O
O
H3C O CH3
aspartame ethanoic anhydride
sweetener acetic anhydride
amide acid anhydride
gjr-–- 21
alkanes
(removal of hydrogen)
alkyl
alcohols ethers amines thiols
halides
aldehydes ketones
Overview
What's next?
• To looking at the bonding in molecules in detail
• To understand how bonding effects the shape of molecules