G3) OUR LADY OF FATIMA UNIVERSITY A] Eater Hydrocarbons: Nomenclature PHARMACEUTICAL MISTRY Types of Nomenclature + systematic Name = Composed wholly or especially coined or selected syllables = Rofersto the structure of compounds + Trivial Name = Aname no part of which is useeina systematiesense ~ Refersto compounds independent of structure ane Sometimes given before the structure s known + Semisynthetic-Semitrivial Name = Aname of which only apart is used ina systematic [ieee Classification of Hydrocarbons * All organic compounds may be divided into two broad classes based upon the pattern of chain of carbon atoms. —Open-chain or Aliphatic compounds =Closed-chain or cyclic compounds * Alicyelie compounds * Aromatic compounds Oo) LNT ciara mai Aliphatic Hydrocarbons + This class includes all hydrocarbons (saturated and unsaturated) and their derivatives which have open-chain structures. — Saturated hydrocarbons are those which contain single bonds between all carbon atoms such as CH,-CH, and CH, -CH,~ CH, @@) Aliphatic Hydrocarbons On the other hand, unsaturated compounds contain a double (C= C-] ra triple -C=C-] bond between two carbon atoms F —cu=a, @@)Cyclic Hydrocarbons + These compounds have atleast one ring (cyclic) system. These are further divided into two sub- classes: homocyclic and heterocyclic based on the atoms present in the ring. They are called homecyclic or carbocyclic when the ring is formed by carbon atoms only. + Homoeyelic (carbocyclic) compounds may again be divided into two groups namely alicyclic and aromatic compounds. ©@) Alicyclic Hydrocarbons + This group includes saturated and unsaturated cyclic hydrocarbons which resemble with the aliphatic hydrocarbons in properties. Some examples are given below: Aromatic + The group of homocyclic compounds having special set of properties are called aromatic compounds. They also have characteristic smell or aroma and hence called aromatic These include aromatic hydracarbions and their derivatives are examples of such compounds are as follows Homologous Series of Hydrocarbons Nomenclature of Organic Compounds + th order to bring uniformity and rationality in naming the ‘organie compounds throughout the word, International Union of chemistry (in 1958) came out with a system of ‘nomenclature later known 2s 1UPAC (International Union of Pure and Applied Chemistry) system, + The purpose ofthe IUPACsystem of nomenclature to ‘establish an international standard of naming compounds to faciltate communication, + The goal ofthe system isto give each structure 2 unique and unambigous name, and to complete each name With a unique and unambigous structure. @@) Nomenclature of Organic Compounds + IUPAC nomenclature is based on naming molecule’s longest chain of carbons connected by single bonds either in chain or in ring *+ Multiple bonds other than Cand H, are Indicated by prefixes or suffixes according to specific set of priorities. Oo)IUPAC Nomenclature of Aliphatic Hydrocarbons + ROOT WORD -It indicates the number af carbon atoms in the longest possible continuous carbon chain also known as parent chain chosen by aset of rules, The roat wards used for different length of carbon chain are shown below. ea ee, IUPAC Nomenclature of Aliphatic Hydrocarbons SUFFIX - It is again divided into two types. i. Primary suffix: It is used to indicate the degree of saturation or unsaturation in the main chain. Itis added immedietely after the root word. li. Secondary suffix: It is used to indicate the main functional group in the organic compound and is added immediately after the 1° suffix @o) ieee in iy Fret occomi) ae er 3 [rawaseee ae Frat ie [trac ore carat Chee fee IUPAC Nomenclature of Aliphatic Hydrocarbons Locant + Denotes the numeral or letter that indicates the sition fof an atom or group in a molecule. + Numerals ~ Numerat se locont when it inaicates the position ofa ubstitaents or bond na stractre ~ seporeted by commas eg. 1.25.6-etrabromocycohexane), Inaspace after the comma a7colon ~ sets of numerals are cine by bypen ~ arranged n ascending order + place as early ina name as toot cause confusion + In branched chain hydrocarbons, one or mare ally! groups + The carbon atoms ofthe side chain constitute alkyl eroups + These ally groups are written as prefines in the IUPAC * Aa alkyl group is cbtaned from an alkane by removing one @@) IUPAC Nomenclature of Acyclic Hydrocarbons fre present ae ado chain atached fa the main rage Chain of earbon atoms hydrogen atom Since the general formula of liane i ChH2nt2, the seneral frmols of ly! group fx CoH. The allyl groups are generally represented by R and named by fepiadng the sulfic “ane of the crtesponding lane by Oo)IUPAC NAME (International Union of ac. | rae Pure and Applied Chemistry) a be Locant/ Suffix! cu, cu-c, | Some Prefix -Root -—Ending cau, cH-cH, Denotes number longest fundaorial clasal on a and identity carbon a ea tenet attached groups chain @o) IUPAC Nomenclature of IUPAC Nomenclature of Acyclic Hydrocarbons Acyclic Hydrocarbons ule 4 Longest chain Rule: ule 4. Longest chain Rul: + According to this rue, the longest possible chain of carbo atom caeired andthe compound ; z is named as the derivative of the correspondin ay alkane penane ,-CH,-CH-CH,-CH, + Sore liste bond is present, the selects | chain must contain the carbon atoms of the trultle bond: The number of earben stom in CH,-CH, the selected chain determines the word root and 7 the saturation or unsaturation wil determine he ‘Wioedrook= lien Seffic~one @¢) @2) IUPAC Nomenclature of Acyclic Hydrocarbons Rule 1, Longest chain Rule: CH; I C,-CH-6-Ces CH, cH, Word root ~ But + Suffixene. @@) IUPAC Nomenclature of Acyclic Hydrocarbons Bule 1, Longest chain Rule: + IF two equally long chains are possible, the chain with maximum number of side chains fs selected as ‘the main chain aon Gf] fi) Oo)IUPAC Nomenclature of Acyclic Hydrocarbons ule 2. Lowest number or lowest sum rule + The longest carbon chain is numbered from one fend to another and the positions of the side chain are indicated by the number of carbon atoms to which these are attached. The ‘numbering is done in such away that ©@) IUPAC Nomenclature of Acyclic Hydrocarbons Rule 2. Lowest number or lowest sum rule: 2) The substituted carbon atoms have the lowest poslbe numbers fan. 22g CH-GHCH-CH, CH -HCHCH GH, CH, IUPAC Nomenclature of Acyclic Hydrocarbons Bule2, Lowest number or lowest sum rule }) The sum of numbers used to indicate the positions of various alkyl groups must be the lowest. CH; CH, s als IUPAC Nomenclature of Acyclic Hydrocarbons ule 3 If some multiple bond is present in the chain the carbon atoms involved in the multiple bond should get the lowest possible numbers. 234 a CH,-CH-CH=CH, CH,-CH-CH=CH, | - I . cH, cH, Oo) LNT ciara mai IUPAC Nomenclature of Acyclic Hydrocarbons Rule 4: Naming of compounds with one alky! group as the substituent (side chain) IUPAC Nomenclature of Acyclic Hydrocarbons Rule 5: Naming the same alkyl groups at different ‘positions or more than one alkyl groups * If the compound contains more than one identical alky! groups, theie positions are indicated separately and the prefixes di (for two}, tri (for three) etc. are attached to the name ofthe substituents + The postions of the substituents are separated by commas (. Oo)IUPAC Nomenclature of Acyclic Hydrocarbons Rule 5: Naming the same alkyl groups at different positions or more than one alkyl groups CH, CH, 1 213 4 3 ct, CH - CH - CH,- CH, ©@) IUPAC Nomenclature of Acyclic Hydrocarbons Rule 6: Naming different ally substituents + ifthere are different alkyl substituents present in the compound, thelr names are written in the alphabetical order. However, the prefixes di, ti, etc, are not considered in deciding the alphabetical order @o) IUPAC Nomenclature of Acyclic Hydrocarbons Rule 6: Naming different alkyl substituents IUPAC Nomenclature of Cyclic Hydrocarbons * Alicyclic compounds have closed chain i.e cyclic structures, hence their names are Cyclic Hydrocarbons a A % le Sea, ¢ i oo a or He Ne ee te, \ J tt & eth ~— Orctohexane yctopentene Oielopontyse GH derived by putting pref ‘elo’ before the , 5 ls : word root, CH,-CH-C-CH,- CH, ‘The suffix ane, ene or yne are written ri. according to the saturation or unsaturation in CH, CH, the ring structure. ©) IUPAC Nomenclature of IUPAC Nomenclature of @@) ‘Cyclic Hydrocarbons A= Aon a6h(O fo 282 Oo)IUPAC Nomenclature of Cyclic Hydrocarbons Aeyclic Compounds: + fan alkyl substituent fs present, tis ndieated by the appropriate prefix and its positions indicated by ‘numbering the carton atoms of the ring in suen 8 Way 0 a8 to assign the least potsible number to the ae | IUPAC Nomenclature of Cyclic Hydrocarbons Aromatic Compounds + The most important members of this cass are benzene and its derivatives + For naming an alky! substituted benzene, the carbon atoms of benzene are numbered from 1 to & by giving the lowest possible number to the position of the side chain or substituent. @o) La NAA COLL PUN IUPAC Nomenclature of Cyclic Hydrocarbons ‘Aromatic Compounds, TC€ Side chain | [1 CH, Side chain Methytbenzene Hthytbenrene (Toluened ©@) IUPAC Nomenclature of Cyclic Hydrocarbons ‘Aromatic Compounds: + Benzene forms only one monosubstituted derivatives ike ethylbenzene or ethylbenzene. SO O88EoS bewasayae peo! ane anit ne (aumnamnsnunsremmermenenan =) IUPAC Nomenclature of Cyclic Hydrocarbons ‘Aromatic Compounds ‘+ However, it can form three dizubstituted compounds ‘namely 1,2; 3,3 and 4,4 derivative IUPAC Nomenclature of ‘Cyclic Hydrocarbons + Common Parent Ring System o-0 oO OOHydrocarbons: Nomenclature PHARMACEUTICA IUPAC Nomenclature of Cyclic Hydrocarbons + Alicyeic compounds have closed chain ie cyclic structures, hence their names are derived by putting prefix ‘cyclo’ before the word root. + The suffix ane, ene or yne are written ce ORGANIC CHEMIS) according to the saturation or unsaturation in PORGII the rng structure IUPAC Nomenclature of IUPAC Nomenclature of Cyclic Hydrocarbons Cyclic Hydrocarbons 1H = ; _ A z % Aa=A« O QO ee Be et ne ions maar lng de \ of 1 ™ me w—d net exam —__rleomant pt Oo oO a ome: mans IUPAC Nomenclature of Cyclic Hydrocarbons Alsi Comeounds: * fan aly substruent is presets indcate by the appropriate peti adits pasitonisindeated by numbering the carbon atomsof the ring in such a way 50 sto assign the least pessble number tethe substituent. \ eg IUPAC Nomenclature of Cyclic Hydrocarbons ‘Aromatic Compounds + The most important members of this class are benzene and its derivatives. + For naming an alkyl substituted benzene, the carbon atoms of benzene are numbered from 1 to 6 by Biving the lowest possible number to the poston of ‘the side chain or substituentIUPAC Nomenclature of Cyclic Hydrocarbons Aromatic Compounds TLC © Side Side chain hain Methistbenzene IUPAC Nomenclature of Cyclic Hydrocarbons ‘Aromatic Compounds: + Benzene forms only one monosubstituted derivatives like ethylbenzene or ethylbenzene. ‘lalusney eg 3) IUPAC Nomenclature of IUPAC Nomenclature of @e& a Cyclic Hydrocarbons The use of Phenyl and Benzyl in Nomenclature 1 the ally group attached to the benzene contains seven or more carbons the compounds is named as Shen ubsttuted lane in Pliers : 6 ; Se The use of Phenyl and Benzyl in Nomenclature + The benzyl group, similar to the phenyl group ‘and can be written as C,H.CH,-R, PACH,R, or BrR ~ For example, aehorine attached toa benayl roup would simply be caled benachovde, whereas an OH group attached to @ benzyl group would simply be called benayl alcohol.The use of Phenyl and Benzyl in Nomenclature IUPAC Nomenclature of Cyclic Hydrocarbons ‘Aromatic Compounds: + Howe can form three disubstituted compounds 4,3 and 1,4 derivatives namely 1, IUPAC Nomenclature of Cyclic Hydrocarbons + any do appeartnn the compounds ratramed as a benzene butwatha dierent paentname. These ‘compounds are named as such = Positon pr Name ofthe substven + Name of arent & & 6 oto cherepanet meta Nitobnaleaekd pao g IUPAC Nomenclature of Cyclic Hydrocarbons + thecomponads reds uth Asli prafi tomo the subsets nlsabettel ore 1 beene Ree er if two ofthe same substituent appears then the prefs Used before tha substtuant'sname, ee IUPAC Nomenclature of Cyclic Hydrocarbons When three ormore substituents are present the ‘ortho, meta, para positional prefixes become Inadequate anda numbering system for the ring ‘must be applied. Se IUPAC Nomenclature of Cyclic Hydrocarbons * Common Parent Ring System 0-0 CO COO _———IUPAC Nomenclature of Alkyl Halides + The common names of alkyl halides consist of ‘two parts: = the name ofthe alky group plus the stem of the fname of the halogen, withthe ending “ie. + The IUPAC system uses the name ofthe parent alkane with a prefoc indicating the halogen substituents, preceded by ‘number indicating the substituent’s location, +The petites are fvro-, chlor, bromo. and iodo: © IUPAC Nomenclature of Alkyl Halides CH,CHCH,CH,CH, Br CHL GCHLCS, cH, Br