Unit One Part 2: naming and functional groups
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1 Unit ne Part 2: naming and functional groups To write and interpret IUPAC names for small, simple molecules gjr- - 1 Identify some common functional groups found in organic molecules 3 C C 3 3 C 3 C S viagra (trade name) sildenafil (trivial name) 5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1-methyl-3-propyl-1pyrazolo[4,3-d] pyrimidin-7(6)-one dr gareth rowlands; g.j.rowlands@massey.ac.nz; science tower a4.12
2 Systematic (IUPAC) naming gjr- - 2 PREFIX PARET SUFFIX substituents / minor functional groups number of C AD multiple bond index principal functional group Comprises of three main parts ote: multiple bond index is always incorporated in parent section o. Carbons Root o. Carbons Root 1 meth 6 hex 2 eth 7 hept 3 prop 8 oct 4 but 9 non 5 pent 10 dec Bond C C C=C C C Multiple-bond index an(e) en(e) yn(e)
3 Systematic (IUPAC) naming: functional groups gjr- - 3 Functional group Structure Suffix Prefix General form acid anhydride acyl chloride ester amide nitrile aldehyde ketone R R R R R R R 2 oic acid carboxylic acid oic anhydride carboxylic anhydride carboxy R-C R-C()C()-R oyl chloride -carbonyl chloride chlorocarbonyl R-C oate carboxylate alkoxycarbonyl R-CR amide carboxamide carbamoyl R-C2 R nitrile cyano R-C R R R al carbaldehyde oxo R-C one oxo R-C-R alcohol R ol hydroxy R- amine R 2 amine amino R-2 ether R R ether alkoxy R--R alkyl bromide (alkyl halide) R Br bromo (halo) R-Br (R-X)
4 omenclature rules gjr Parent - root derived from number of carbon in longest unbranched chain.containing functional group 3 C C 3 4-methylheptane C 3 3 C C 3 2-propyl-1-pentanol Suffix - basic name derived by adding ending of major functional group (FG) C 3 3 C butanoic acid 3 C 2 3-methylbutanamide 3. Position - position of FG denoted by Arabic numeral placed before whole...name or just before ending. umbering achieves lowest number for FG 3 C C 3 2-pentanone pentan-2-one T 4-pentanone
5 omenclature rules II 4. Prefix - substituents are designated by prefix & Arabic number indicating...position (lowest possible numbering) gjr- - 5 C 3 C 3 3 C C 3 3 C C 3 2,2,5-trimethylheptane T 3,6,6-trimethylheptane 3 C C 3 C 3 8-chloro-2,3-dimethylnonane T 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 3 C C 3 5-hydroxy-2,2-dimethylpentanoic acid C 3 3 C 2-methyl-4-oxohex-2-enoic acid 6. Minor FG - halo-, nitro- (-2), nitroso- (-) & azo- (-2-) are considered...substituents & not FG for nomenclature only 7. rder - substituents are written in alphabetical order
6 Examples: structure to name gjr C C 3 3 C C 3 -ethyl-3-hydroxy-5-methylhept-6-enamide Step 1: root Step 7: complete 3 C hept C 3 3 C C hydroxy-5-methylhept-6-enamide Step 2: suffix Step 5: substituents (prefix) 3 C hept amide C 3 3 C 3 1 C hydroxyhept-6-enamide Step 3: multiplebond index 3 C hept-6-enamide C 3 Step 4: functional groups (prefix)
7 Examples: name to structure Draw the structure for 4-ethyl-3-hydroxycyclohexanone (please) gjr- - 7 draw the root 4-ethyl-3-hydroxycyclohexanone add major functional group 4-ethyl-3-hydroxycyclohexanone 3 C add substituent 4-ethyl-3-hydroxycyclohexanone 3 C add minor functional group 4-ethyl-3-hydroxycyclohexanone
8 gjr- - 8 Functional groups: alkanes Saturated hydrocarbons - contain only C & and no multiple bonds on-cyclic alkanes have the formula Cn2n+2 C methane C4 propane C38 pentane C512 cyclopentane C510 C4 Alkanes are a little dull - used as solvents or burnt as fuel Methane is a fuel, a chemical feedstock & a green house gas propane
9 Functional groups: alkanes II gjr- - 9 isooctane 2,2,4-trimethylpentane C 8 18 Isooctane is used in petrol - branched structure means it burns smoothly ctane is a long change and burns explosively ctane 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 pentane bp 36.2 C 2-methylbutane bp 28 C 2,2-dimethylpropane bp 9.6 C
10 Functional groups: alkenes gjr ethene Ethene - simplest alkene. Very important industrially Carbon is trigonal planar - flat and triangular! ew form of isomerism - configurational isomers All atoms bonded in the same manner but different orientation in space C 3 1-butene C C C 3 3 C trans-2-butene 2-butenecis-2-butene C methylpropene C 4 8 cyclobutane C 4 8 C 3 3 C C 3 C 3 C 3 3 C (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene α-pinene
11 gjr Functional groups: alkynes & cyclic structures ethyne C22 3C pent-3-yn-1-ol T pent-2-yn-5-ol ME 3C Ethyne is an explosive gas Triple bond makes molecular linear (cylinder) Examples found in nature (example cleaves DA) Me C3 neocarzinostatin chromophore A Cycloalkanes and cycloalkenes cyclopropane 3C C3 1,3-dimethylcyclohexane cyclohexene Cyclic hydrocarbons are common - note that most are not flat benzene
12 Cyclic structures in nature 3 C C 3 C 3 C 3 3 C gjr (8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-(6- methylheptan-2-yl)-hexadecahydro-1cyclopenta[a]phenanthrene cholestane - steroid Ring systems are common in natural products & pharmaceuticals Example below shows the importance of another form of isomerism - stereoisomers 3 C C 3 3 C C 3 (R)-1-methyl-4-(prop-1-en-2- yl)cyclohex-1-ene (R)-limonene smells of oranges (S)-1-methyl-4-(prop-1-en-2- yl)cyclohex-1-ene (S)-limonene smells of lemons
13 Functional groups: alcohols gjr primary (1 ) 3 C C 3 C 3 tertiary (3 ) 3 C C 3 C 3 C 3 3 C C 3 3 C (R)-3,7-dimethyloct-6-en-1-ol citronellol citronella oil secondary (2 ) cholesterol all animals C 3 (R)-1-isopropyl-4- methylcyclohex-3-enol terpinen-4-ol tea tree oil Alcohols contain (hydroxy) group Found in many natural systems (especially on Friday night) Three classes depending on how many C attached to C Compounds can have more than one (improves water solubility) 1,2-ethandiol ethylene glycol antifreeze 6-(hydroxymethyl)-tetrahydro- 2-pyran-2,3,4,5-tetraol glucose sugar I guess!
14 Functional groups: phenols and ethers Phenols gjr phenol carbolic acid 2,4,6-trichlorophenol TCP antiseptic Phenols are distinct from alcohols as attached to phenyl ring - acidic Ethers 3 C C 3 ethoxyethane diethyl ether ether tetrahydrofuran TF 18-crown-6 Most commonly used as solvents 18-Crown-6 enables metal cations (M + ) to dissolve in organic solvents
15 Functional groups: alkyl halides and thiols dichloromethane DCM Alkyl halides are incredibly useful compounds - used extensively Down side is they appear to be bad for us and the environment F F dichlorodifluoromethane Freon (refrigerant) a CFC Thiols dieldrin 2 S C 2 (R)-2-amino-3- sulfanylpropanoic acid cysteine S 3 C C 3 C 3 2-(4-methylcyclohex-3- enyl)propane-2-thiol taste of grapefruit S S C 3 S 3 C C 3 3 C C 3 propane-2,2-dithiol gjr methyl-4- sulfanylpentan-2-one Thiols are the sulfur analogue of alcohols - and they smell, bad... umans can detect 2x10 5 ppb of the second compound (1 drop in a lake) ne of the last two compounds is the smelliest known - but no one is...prepared to make them again to find out which!
16 Functional groups: amines 3 C C 3 C 3 triethylamine smells of fish 2 2 butane-1,4-diamine putrescine smells of decay 2 (S)-2-amino-3-phenylpropanoic acid phenylalanine amino acid Vital in biological systems Many smell (bad but not as bad as thiols) Found in many compounds that are physiologically active... C 3 gjr (S)-3-(1- methylpyrrolidin-2-yl) pyridine nicotine C 3 C 3 methyl 3-(benzoyloxy)-8-methyl- 8-aza-bicyclo[3.2.1]octane-2- carboxylate cocaine
17 Functional groups: amines II gjr ammonia 3 C 2 methylamine 1 amine 3 C C3 dimethylamine 2 amine 3 C C3 3 C trimethylamine 3 amine Just to confuse, amines are labeled by the number of C attached This is different to alcohols (labeled by C attached to C ) 3 C primary amine (1 ) secondary position (2 ) C 3 2 valine 3 C C3 3 C trimethylammonium ion 4 ammonium (salt) If add four groups everything changes!
18 Functional groups: the carbonyl group gjr Carbonyl group C= analogous to alkene Two groups, aldehydes RC and ketones R2C= Aldehyde methanal formaldehyde 3 C ethanal acetaldehyde benzaldehyde (2R,3S,4R,5R)-2,3,4,5,6- pentahydroxyhexanal glucose Ketones C 3 C 3 3 C C 3 3 C C 3 3 C propanone acetone (R)-2-methyl-5-(prop-1-en- 2-yl)cyclohex-2-enone (R)-carvone spearmint (S)-2-methyl-5-(prop-1-en- 2-yl)cyclohex-2-enone (S)-carvone caraway 4-(4-hydroxyphenyl) butan-2-one raspberry ketone
19 Functional groups: carboxylic acids & derivatives gjr R C hydrocarbon oxidation reduction R C alcohol oxidation reduction R C aldehyde oxidation reduction R C carboxylic acid Many of the functional groups are 'linked' If we replace one C at a time by a C we see how these groups relate 3 C ethanoic acid acetic acid vinegar 2 C C 2 maleic acid 3 C (S)-2-hydroxypropanoic acid L-(+)-lactic acid 3 C C 3 C 3 C 2 C 3 (2Z,4E)-3-methyl-5-(2,6,6- trimethyl-4-oxocyclohex-2- enyl)penta-2,4-dienoic acid abscisic acid leaf fall
20 Functional groups: derivatives gjr C ethanoic acid + a sodium hydroxide a + 3 C sodium ethanoate water carboxylate ion Reaction of a carboxylic acid with a base (eg. a) gives carboxylate ion 3 C C 3 ethyl ethanoate ethyl acetate solvent ester 2 C 2 aspartame sweetener amide 3 C Derivatives C 3 C 3 2-methylpropyl propanoate isobutyl propionate smell of rum ester Me 3 C C 3 benzoyl chloride acid chloride ethanoic anhydride acetic anhydride acid anhydride
21 assification of functional groups gjr Functional groups can be classed by the degree of oxidation (removal of ) increasing degree of oxidation (removal of hydrogen) alkanes alcohols ethers amines aldehydes ketones carboxylic acids esters amides alkyl halides acyl chlorides thiols acid anhydrides nitriles R C hydrocarbon oxidation reduction oxidation oxidation R C R C R C reduction reduction alcohol aldehyde carboxylic acid
22 verview gjr What have we learnt? ow to name simple organic molecules To recognise common functional groups Common examples of these functional groups What's next? To looking at the bonding in molecules in detail To understand how bonding effects the shape of molecules dr gareth rowlands; g.j.rowlands@massey.ac.nz; science tower a4.12
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