Identify some common functional groups found in organic molecules 1 List of priorities given in course notes Multiple bonds are added to parent (end),
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[PDF] Unit One Part 2: naming and functional groups
Identify some common functional groups found in organic molecules 1 List of priorities given in course notes Multiple bonds are added to parent (end),
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Unit One Part 2: naming and functional groups
gjr---• To write and interpret IUPAC names for small, simple molecules• Identify some common functional groups found in organic molecules
1 viagra™ (trade name) sildenafil (trivial name) pyrazolo[4,3-d] pyrimidin-7(6H)-one N N N N S N N H 3 C H 3 C O O CH 3 H 3 C O O H dr gareth rowlands; g.j.rowlands@massey.ac.nz; science tower a4.12 http://www.massey.ac.nz/~gjrowlanSystematic (IUPAC) naming
gjr---• Comprises of three main parts• Note: multiple bond index is always incorporated in parent section
2 substituents / minor functional groups number of CAND multiple bond
index principal functional groupSUFFIXPREFIXPARENT
No. CarbonsRootNo. CarbonsRoot1meth6hex
2eth7hept3prop8oct4but9non5pent10dec
BondMultiple-bond
indexC-Can(e)C=Cen(e)C㲇Cyn(e)
Systematic (IUPAC) naming: functional groups
gjr--- 3Functional groupStructureSuffixPrefixGeneral form
acid ROH O -oic acid -carboxylic acid carboxyR-COOHanhydride ROR OO -oic anhydride -carboxylic anhydrideR-C(O)OC(O)-Racyl chloride
RCl O -oyl chloride -carbonyl chloride chlorocarbonylR-COClester ROR O -oate -carboxylate alkoxycarbonylR-COORamide RNH 2 O -amide -carboxamide carbamoylR-CONH 2 nitrile NR -nitrilecyanoR-C㲇N aldehyde RH O -al -carbaldehyde oxoR-CHOketone RR O -oneoxoR-CO-R alcohol ROH -olhydroxyR-OHamine RNH 2 -amineaminoR-NH 2 ether R O R -etheralkoxyR-O-R alkyl bromide (alkyl halide) RBr bromo (halo) R-Br (R-X)Nomenclature rules
gjr--- H 3 CCH 3 CH 34-methylheptane
H 3 C CH 3 OH2-propyl-1-pentanol
1 2 3 4 5 H 3 COH O butanoic acid H 3 CNH 2 OCH 33-methylbutanamide
H 3 CCH 3 O2-pentanone
pentan-2-oneNOT 4-pentanone
1. Parent - root derived from number of carbon in longest unbranched chain
.containing functional group 42. Suffix - basic name derived by adding ending of major functional group (FG)3. Position - position of FG denoted by Arabic numeral placed before whole
....name or just before ending. Numbering achieves lowest number for FGNomenclature rules II
gjr--- H 3 CCH 3 H 3 CCH 3 CH 32,2,5-trimethylheptane
NOT 3,6,6-trimethylheptane
H 3 CCH 3 CH 3 CH 3 Cl8-chloro-2,3-dimethylnonane
NOT 2-chloro-7,8-dimethylnonane
54. Prefix - substituents are designated by prefix & Arabic number indicating
....position (lowest possible numbering)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 prefixes6. Minor FG - halo-, nitro- (-NO
2 ), nitroso- (-NO) & azo- (-N 2 -) are considered ....substituents & not FG for nomenclature only7. Order - substituents are written in alphabetical order
HOOH O H 3 CCH 35-hydroxy-2,2-dimethylpentanoic acid
CH 3 OH O O H 3 C2-methyl-4-oxohex-2-enoic acid
Examples: structure to name
gjr--- 6Step 1: rootStep 3: multiple-
bond index H 3 CN H O CH 3 OH H 3 CN H O CH 3 OH hept H 3 CN H O CH 3 OH hept-6-enamide 1 2 3 4 5 6 H 3 CN H O CH 3 OH 1 2 33-hydroxyhept-6-enamide
H 3 CN H O CH 3 OH hept amideStep 2: suffixStep 4: functional
groups (prefix) H 3 CN H O CH 3 OH 1 2 3 4 53-hydroxy-5-methylhept-6-enamide
Step 5: substituents
(prefix) H 3 CN H O CH 3 OHN-ethyl-3-hydroxy-5-methylhept-6-enamide
Step 7: complete
Examples: name to structure
gjr--- • Draw the structure for 4-ethyl-3-hydroxycyclohexanone (please) 7 OO H 3 C O H 3 C OH draw the root4-ethyl-3-hydroxycyclohexanone
add major functional group4-ethyl-3-hydroxycyclohexanone
add substituent4-ethyl-3-hydroxycyclohexanone
add minor functional group4-ethyl-3-hydroxycyclohexanone
Functional groups: alkanes
gjr---• Saturated hydrocarbons - contain only C & H and no multiple bonds• Non-cyclic alkanes have the formula C
n H 2n+2 8 H C H H H methane CH 4 propane C 3 H 8 pentane C 5 H 12 cyclopentane C 5 H 10• Alkanes are a little dull - used as solvents or burnt as fuel • Methane is a fuel, a chemical feedstock & a green house gas
propane CH 4Functional groups: alkanes II
gjr---• Isooctane is used in petrol - branched structure means it burns smoothly• Octane is a long change and burns explosively• Octane number of petrol is based on isooctane = 100 & heptane = 1
Unleaded 91 petrol = 91% isooctane & 9% heptane
• Structural isomers have same formula but different atoms joined differently• Isomers can have very different properties
9 isooctane2,2,4-trimethylpentane
C 8 H 182,2-dimethylpropane
2-methylbutane
pentaneFunctional groups: alkenes
gjr---• Ethene - simplest alkene. Very important industrially• Carbon is trigonal planar - flat and triangular!
10 H HH H ethene CH 3 H 3 C H 3 C CH 3 CH 3 H 3 C