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IB Chem, Topic 10, IUPAC Organic Nomenclature

IB Chem, Topic 10, IUPAC Organic Nomenclature

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1http://guidesbyjulie.blogspot.com/IB Chemistry: Topic 10: Organic Chemistry
IUPAC Organic Nomenclature
CONTENTS
 
Basic Rules
 
Root Prefixes, Multipliers
 
Structure of a Name
 
Functional Groups (listed in decreasing priority order)1.
 
Carboxylic Acid2.
 
Ester3.
 
Amide4.
 
Nitrile5.
 
Aldehyde6.
 
Ketone7.
 
Alcohol8.
 
Amine9.
 
Alkene10.
 
Alkyne11.
 
Alkyl12.
 
Halogen13.
 
Nitro14.
 
Phenyl
 
Aromatic CompoundsBASIC RULESThe longest continuouslongest continuouslongest continuouslongest continuous chainchainchainchain of hydrocarbons is referred to as the parent chain. The length of the parentchain determines the root name, which can then be modified according to the presence of functionalgroups.When naming an organic molecule, follow these steps:1.
 
Principal fuPrincipal fuPrincipal fuPrincipal functional group:nctional group:nctional group:nctional group: Identify the principal functional groupprincipal functional groupprincipal functional groupprincipal functional group, which will determine whatclass the compound belongs to. The principal functional group is the highest priority group presentand is given the lowest locant (numbering) possible.2.
 
Longest chain:Longest chain:Longest chain:Longest chain: The longest continuous chainlongest continuous chainlongest continuous chainlongest continuous chain containing the principal functional group definesthe root name. Other groups attached are referred to as substituentssubstituentssubstituentssubstituents. If there are two chains ofequal length, then the one containing the simplest substituents is chosen.3.
 
NumbeNumbeNumbeNumbering:ring:ring:ring: The locantslocantslocantslocants are the numbers that define the positions of the principal functional groupand substituents. Start from the end of the molecule that assigns the lowest number to theprincipal group.a.
 
First point of differenceFirst point of differenceFirst point of differenceFirst point of difference: The principal functional group is given the lowest locant, thensubstituents are labeled in a way to give the lowest number at the first difference.b.
 
ONLY if there is no first point of difference, alphabetization will determine numbering.4.
 
Alphabetization:Alphabetization:Alphabetization:Alphabetization: Substituents are cited in alphabetical orderalphabetical orderalphabetical orderalphabetical order. Prefixes (di-, tri-,
sec-,
 
tert-,
etc.)are ignored, but iso- and cyclo- are included, because they are used without hyphens and are partof the substituent name.
 
2http://guidesbyjulie.blogspot.com/IB Chemistry: Topic 10: Organic Chemistry
IUPAC Organic Nomenclature
First Point of Difference Examples2222----methylpentanemethylpentanemethylpentanemethylpentane
not 
 4-methylpentane.Here the methyl group is given the lowest number by numberingas shown.2,2,42,2,42,2,42,2,4----trimethylpentanetrimethylpentanetrimethylpentanetrimethylpentane
 not 
 2,4,4-trimethylpentaneThe first difference is in the
 
second 
locant - by numbering asshown this is kept lower (2- rather than 4-).2,4,42,4,42,4,42,4,4----trimethylhexanetrimethylhexanetrimethylhexanetrimethylhexane
not 
 3,3,5-trimethylhexaneThe first difference is in the
 
first 
 
locant - by numbering as shownthis is kept lower (2 rather than 3).1111----ethylethylethylethyl----2222----methylcyclohexanemethylcyclohexanemethylcyclohexanemethylcyclohexane
 not 
 
2-ethyl-1-methylcyclohexane
or 
 
1-ethyl-6-methylcyclohexaneThe numbering is determined by thealphabetization:
 
ethyl
 
precedes
 
methyl, so ethyl gets the lowernumber. But then we number counter-clockwise to give themethyl the lower number (2- vs. 6-)2222----pentanolpentanolpentanolpentanol
not 
 4-pentanolHere the principle functional group, the alcohol -OH is give thelowest locant by numbering as shown.3333----pentanolpentanolpentanolpentanol
 
no choice! 
 No matter which way this is numbered, the -OH is at C3.4444----methylmethylmethylmethyl----2222----pentanolpentanolpentanolpentanol
not 
 2-methyl-4-pentanolThe first difference is in the -OH locant - by numbering as shownthis is kept lower (2- rather than 4-).2222----methylmethylmethylmethyl----3333----pentanolpentanolpentanolpentanol
not 
 4-methyl-3-pentanolThe first difference is in the methyl locant - since the -OH must beat C3 either way, but by numbering as shown the methyl locantkept lower (2- rather than 4-).Examples from <http://www.chem.ucalgary.ca/courses/351/orgnom/main/difference.html>
 
3http://guidesbyjulie.blogspot.com/IB Chemistry: Topic 10: Organic Chemistry
IUPAC Organic Nomenclature
ROOT PREFIXES, MULTIPLIERS*The multiplier mono is not necessary for organic chemistry.STRUCTURE OF A NAMEFunctional Group SuffixFunctional Group SuffixFunctional Group SuffixFunctional Group Suffix: Added to the end of a name—based on principal functional group.RootRootRootRoot:Based on the length of the parent chain.Substituent PrefixesSubstituent PrefixesSubstituent PrefixesSubstituent Prefixes: Additional groups are added to the beginning of the name in alphabetical order.MultiplierMultiplierMultiplierMultiplier: If a group occurs more than once, a multiplier denotes how many times it occurs.LocantsLocantsLocantsLocants: Numbers that define the position of the principal functional group and substituents. The locant forthe principal function group is placed before the functional group suffix.Root PrefixesRoot PrefixesRoot PrefixesRoot Prefixes# of Carbons Hydrocarbon Prefix1 Meth—2 Eth—3 Prop—4 But—5 Pent—6 Hex—7 Hept—8 Oct—9 Non—10 Dec—MultipliersMultipliersMultipliersMultipliers# Prefix1 Mono
 
—*
 
2 Di—3 Tri—4 Tetra—5 Penta—6 Hexa—7 Hepta—8 Octa—9 Nona—10 Deca—

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