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    Short Summary of IUPAC Nomenclature of Organic Compounds PDF

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    ARVINE JUSTINE CORPUZ

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    Short Summary of IUPAC Nomenclature of Organic Compounds Introduction ‘The purpose ofthe TUPAC system of nomenclature is to establish an international standard of naming compounds to facilitate communication. The goal ofthe system is to give each structure unig and unambiguous name, and coate cach ae with niga and unambiguous ‘ure 1 smental Principle TUPAC tomate ebaid on naming a molecule’ longest chain of arbons connected by single bonds, whether in @ continuous chain or in aring. All deviations, either multiple bonds or ‘atoms other than carbon and hydrogen, are indicated by prefixes or suffixes according to @ specific set of priorities. IL. Alkanes and Cyel Alida eloped yéioGaons hati, molcale conning carbon ed hhydrogen connected by single bonds only. ‘These molecules can be in continuous chains (called linear or acyclic), or in rings (called cyclic or alicyclic). The names of alkanes and cycloalkanes are the root names of organic compounds, Beginning wit the five-cazbon alkane, the number of | ‘carbons in the chain is indicated by the Greek or Latin prefix. Rings are designated by the prefix Cyclo" (nthe geometrical symbols for ings, ech apex represents a carbon with the number of hydrogens required tills valence) CHa ‘methane CH3[CHa]iCH3 —dodecane (CH3CH3 ethane (CH3[CH2]1;CH3 —_tridecane (CH3CH7CH3 Propane (CH3[CH2]12CH3 _tetradecane CH3[CH2},CH3 butane CH3[CHa]isCH3 —_icosane CH3[CH2};CH3 pentane CH3[CH3}i9CH3—_henicosane CH3[CH2]CHs hexane CH3[CH3]20CH3 —docosane (CH3[CH2}sCH3, heptane CH3[CH2}2;CH3 —_tricosane CH3[CH2}CH3 octane CH3[CHg}sCH3 —_triacontane (CH3[CH2})CH3 nonane (CH3[CH2}29CH3 _hentriacontane (CH3[CH2]sCH3 decane CH3[CH2}sgCH3 _tetracontane CH3[CH2jeCHs —_undecane CH3[CHa]4sCH3 —_pentacontane aaa G See cyclopropane =H H cyclobutane 0 00 cyclohexane ceycloheptane cyclooctane ‘Short Summary of TUPAC Nomenclature, p. 2. TIL, Nomenclature of Molecules Cé iubstituents and Functional Grou A. Priorities of Substituents and Funetional LISTED HERE FROM HIGHEST TO LOWEST PRIORITY, except thatthe substituents within Group C have equivalent priority. Group A—Functional Groups Indicated By Prefix Or Suffix Family of Co Structure Prefix Sultix 0 Carboxylic Acid R=C-OH | exbowye oie acid Cearboxyl i Aldehyde R-C=H ox0- al ° (formy)__(carbaldehyde) i Ketone ROCK oxo. one ‘Alcohol R-O-8 hydroxy al Asin Rone aio. amine i! ‘roup B—Functional Groups Indicated Oni Family of Compound Structure Prefix Sullix Nuh Alkene cae oo / Alleyne c— — -yne Group C—Substituents Indicated by Prefix Only Substiuent Structure Prof Suffix Alkyl (See list below) R= alkyl =, Alkoxy RLo~ alkoxy- sees Halogen FH ‘uoro- ce chloro- Br— bromo- IS jodo- Group C continued on next page Short Summary of IUPAC Nomenclature, p. 3 Group C—Substtuents, continued Fiscellancous substiuens and their prefixes eis eemaw riaamen” =X nitro vinyl ll ny allyl soasl Common aly groups—replace “anc” ending of alkane name with “". Alternate names for ‘complex substitients are given in rackes. cH, cs (Hs methyl —@ —H cH ‘CH,CH, —cH,cH, isopropyl sec-butyl ethyl [I-methylethyl] [I-methylpropy!] ci cH —CH,CH,CH, cha tc, ‘propyl (propyl) ea bi isobutyl tert-butyl or ebutyl —CH,CH,CH,CH, [2-methytpropy!) [1,F-dimethylethyt] ‘bury n-butyl) 'B. Naming Substituted Alkanes and Cycloalkanes—Group C Substituents Only 1, Orsaic compounds conning substvents fom Group C ae named following this Sequence Gf Sepmas ined on the examples below “Sep Fn he ges neon, Deine he ot mame ris parent chien eyelic compound, tering sully considered the parent cain, unless itis Echod to long chino cartons ndcte ang wi the reticle” Before the oot tame (When here ae wo longest cain of cq length, ue the earn with the pester number of subsients) “Step 2, Number the chin in the direction such tat the postion number ofthe st substituent te smaller number. Ifthe ist subatiten's from ether end have the same number, then numbers thatthe second substituent has the smaller number, ee “Step. Determine the name and poston numberof each substituent. (A substeat on a nizogin designated with an "Nisead of «number, sex Seton ILD. below.) “Sep nd te nmi ntl pup yh preines t,e o. ‘Step 5; Plice the poston umber and aames of the sbatuent groups, aphid ex ete to oa, naan ore pei ike or cb ine joo. Always include «postion number for each subsitent, regardless of redundancies, Ee an rc Short Summary of IUPAC Nomenclature, p.4 1s anfoncnc exon) CH, — CH—cH—C— cu cr, CHy— = CH CHCA, | [ATER Hr GeH, oyu pac] ob _ Gi, by & Sromo2-dlonS-tiy-44-dimeilocane 3-A hry 2-metteptane HyC-cHCR.CH, J 1 -see-butyl-3-nitrocyclohexane 4 % (Gqumbering determined by the : alphabetical order of substituents) NO; C. Naming Molecules Containing Funct ps B—Suffix Onl 1. Alkenes—Follow the same steps as for alkanes, except: ‘a. Number the chain of carbons that includes the C=C so that the C=C has the lower position number, since it has a higher priority than any substituents; ’. Change “ane” to “ene” and assign a position number to the first carbon of the C=C: ©. Designate geometrical isomers with a cis rans or E,Z prefix. rE E CH (CH CH- CH= CH, Xe (C— CH: 7 cnc —cu= cn, eal ° ie 1 4 Fo CH Foc 4,4-difluoro-3-methylbut-I-ene 1,1-difluoro-2-methyl- — bul iene S-natilesopen diene ‘Special case: When the chain cannot include the C=C, a substituent name is used. 2. Alkynes—Follow the same steps as for alkanes, except: 1. Number the chain of carbons hat includes the CEC so thatthe functional group has the lower position number; . Change “ane” to "yne” and assign a position number to the frst carbon ofthe CC. Noe: The Group B functional groups (alkene and alkyne) are considered to have equal priory Ina molecule wth bths double and rile bond, whichever is clost othe end ofthe chan, determines the dteetion of numbering Inthe ease where each would have the sume positon fumber, te double bond takes the lower number. Inthe name, “ene” comes Before ye" beeaue of sipabetiaton. Se examples on next pape Short Summary of IUPAC Nomenclature, p. 5 R 4 \ aay as Regs PEO CU— CECH HC=EC—C=CHCH, HC=C—CH,CH= CH, ¥oby, pent -n-1yne pet-I-en-yne ("yne" closer to end “ene” and "yne" have equal 44-

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