Organic Compounds Nomenclature Notes PDF

Nomenclature of Organic Compounds    DISCLAIMER “The content provided herein are created and owned by various authors and licensed to Sorting Hat Technologies Private Limited (“Company”). The Company disclaims all rights and liabilities in...

Nomenclature of Organic Compounds    DISCLAIMER “The content provided herein are created and owned by various authors and licensed to Sorting Hat Technologies Private Limited (“Company”). The Company disclaims all rights and liabilities in relation to the content. The author of the content shall be solely responsible towards, without limitation, any claims, liabilities, damages or suits which may arise with respect to the same.”    Introduction of Organic Compounds Why is an entire branch of chemistry devoted to Introduction the study of carbon containing compounds? y We study organic chemistry because just Organic chemistry and you about all of the molecules that make life y You are already a highly skilled possible—proteins, enzymes, vitamins, lipids, organic chemist. As you read carbohydrates, and nucleic acids—contain these words, your eyes are carbon, so the chemical reactions that take place using an organic compound in living systems, including our own bodies, are (retinal) to convert visible light organic reactions. into nerve impulses. y When you picked up book, your y Most of the compounds found in nature—those muscles were doing chemical we rely on for food, medicine, clothing (cotton, reactions on sugars to give you wool, silk), and energy (natural gas, petroleum). the energy you needed. Berzelius Vital Force Theory y According to vitalism, organic compounds were only those that came from living organisms, and only living things could synthesize organic compounds through intervention of a vital force. y Inorganic compounds were considered those compounds that came from nonliving sources. y Because chemists could not create life in the laboratory, they assumed they could not create compounds with a vital force. With this mind-set, you can imagine how surprised chemists were in 1828 when Friedrich Wohler produced urea—a Introduction of Organic Compounds compound known to be excreted by mammals— by heating ammonium cyanate, an inorganic mineral. Definition y Failure of Berzelius vital theory and synthesis of Old definitions of Organic first organic compound. Compounds y Compounds which we can derive from living organisms (Plants & Animals) are called organic compounds Compounds Source 1. Formic acid Ant 2. Sugar Sugarcane 1.  y Specialized field of chemistry called organic chemistry, which derives its name from the fact that in the 19th century most of the them are known carbon compounds were considered to have originated in living organisms Derivatives of Hydrocarbon y If we replace one or more than Hydrogen from Hydrocarbon by an atom or group of atoms then compound formed is called derivative of Hydrocarbon. −H Acetone is used in some nail polish C2H6  +OH → C2H5OH removers ethanol Hydrocarbon Hydrocarbon derivative Definition * Some Properties of Carbon Modern Definition of Organic Catenation : Compounds y Due to catenation properties of carbon, it can form y Hydrocarbon and their derivatives are called organic long bonded covalent structures. (Chain form) compounds. y Carbon can form single, double or triple bond y Compounds containing carbon (covalent). and Hydrogen only are called Eg.: Alkanes → CnH2n+2 Hydrocarbons. Alkenes → CnH2n Alkynes → CnH2n–2 Point to remember y Carbon in general shows valency 4. y Some Compounds may appear (ability to form bond with carbon or other atoms.) as organic compounds but they Introduction of Organic Compounds y It is not necessary to show valency 4. It may be are actually inorganic e.g., CO2, variable sometime. NaHCO3, H2CO3. An RNA molecule 2. Types of Formula Definition 1. Molecular formula : Example : Formula which represent actual number of atoms in a molecule. (i) Water → H2O (ii) Sulphuric Acid → H2SO4 2. Empirical formula : Definition Example : Formula which represents the Molecular formula Empirical formula simplest ratio of atoms present in (i) Glucose C6H12O6 C1H2O1 it. (ii) Propene C3H6 C1H2 3. Structural formula : Definition Example : H2SO4 Formula which shows connectivity between atoms and groups. * Representation of Organic Compounds Organic chemists use a variety of formats to Introduction of Organic Compounds write structural formulas 4. Dash-formula : Definition Dash structural formulas have lines that show bonding electron pairs, and include elemental symbols for all of the atoms in a molecule. 3.  Q (i) C2H6 (ii) C4H8 (iii) C3H4 Sol 5. Condensed Structural Formulas : Definition In fully condensed formulas, all of the atoms that are attached to the carbon are usually written immediately after that carbon, listing hydrogens first. Introduction of Organic Compounds Q Examples (Unsolved) (a) C2H6 → (b) C3H6 → (c) C5H10 → (d) C4H10 → Sol (a) H3C – CH3 CH2 (b) H3C – CH = CH2 or H2C — CH2 (c) H2C = CH – CH2 – CH3 (d) H3C – CH2 – CH2 –CH3 4. 6. Bond-Line Formulas : Definition Examples : The most common type of structural formula used by organic chemists, and the fastest to draw, is the bond-line formula. (Some chemists call these skeleton formulas.) Note : Bond line notation : Š If the compound has any Terminal points and bends represent C, all hetroatom it will be shown other valencies are filled by H. Hydrogen atom any hydrogen atom attached attach to carbon is not shown. with it will also be shown. Examples : Degree of Carbon : Introduction of Organic Compounds Degree of a given carbon means number of carbon atoms directly attached to particular carbon atom has to be considered. 1° carbon → Attached to 1C – also known as primary carbon 5.  2° carbon → Attached to 2C – also known as secondary carbon 3° carbon → Tertiary carbon 4° carbon → Quaternary carbon Degree of Hydrogen : Similarly we define degree of H atom as the degree of carbon atom to which it is attached. 1° H → Attached to 1° C 2° H → Attached to 2° C 3° H → Attached to 3° C 4° H → Not possible Example : Introduction of Organic Compounds Q Compound 1°C 2°C 3°C 4°C 1°H 2°H 3°H O (i) (ii) (iii) (iv) Sol Compound 1°C 2°C 3°C 4°C 1°H 2°H 3°H (i) 4 0 0 1 12 0 0 6.  (ii) 0 6 0 0 0 6 0 (iii) 2 8 0 2 6 16 0   (iv)   0 6 0 0 0 10 0 Degree of Alcohols : Example : Note : Š Alcohols are hydrocarbon that contains –OH (hydroxy) group. Š Degree of alcohol is degree of carbon atom to which –OH group is attached. Q Identify the degree of given alcohols OH Introduction of Organic Compounds OH (i) (ii) (iii) (iv) HO OH Sol (i) 1° (ii) 3° (iii) 2° (iv) 3° 7.  Degree of Alkyl halide (R–X) : Definition (i) H3C – CH2 – Cl 1° halide Degree of alkyl halide is the degree of carbon atom directly attached to halogen. (ii) CH3 – CH – Cl 2° halide CH3 CH3 (iii) CH3 – C – Cl 3° halide CH3 Q Identify the degree of given halides : Cl (i) Cl (ii) (iii) (iv) F Br Sol (i) 3° (ii) 2° F Cl (iii) 3° (iv) 2° Introduction of Organic Compounds Br Degree of Amines (R–NH2) : Degree of amines is numbers of carbon atoms directly attached with nitrogen. Examples : CH3–NH2 (1° amine) CH3 –NH–CH3 (2° amine) (3° amine) 8. Q Identify the degree of given amines (1°, 2°, 3° amine) : NH2 N (i) (ii) H N (iii) N (iv) Sol S.No. Compound 1° 2° 3° amine (i) ü × × (ii) × × ü    (iii) ×   × ü (iv) × × ü Introduction of Organic Compounds 9.  Functional Groups and Classification Functional groups Definition Part of the molecules which are responsible for the characteristics chemical reactions of those molecules. TYPE OF FUNCTIONAL GROUPS H2C = CH2 (Alkene) R–CH=N–R (Imine) CH ≡ CH (Alkyne) O O R–OH (Alcohol) R–SH (Thio alcohol) R–C–O–C–R (Anhydride) R–O–R (Ether) R–S–R (Thio ether) R–CH=O (Aldehyde) O (Phenol) R–C–R (Ketone) R–COOH (Carboxylic acid) R–SO3H (Sulphonic acid) (Aniline) R–C≡N (Cyanide) R–N≡C (Isocyanide) O R–C–OR (Ester) O (Naphthol) R–C–NH2 (Amide) O R–NH2 (1° amine) Functional Groups and Classification R–C–X (Acid halide) R–NH–R (2° amine) R–N=O (Nitroso) (3° amine) –N=N– (Azo) Type of functional groups : Point to remember Due to difference in their properties 1°, 2°, 3° amine are treated as different functional groups but primary, secondary and tertiary alcohols are considered as same functional groups. 10. Q Identify the function group present in given molecule and encircle them: Cl HS OH O Sol Q Identify the function group present in given molecule and encircle them: O N NC H OH O ketone 2º amine Sol N Functional Groups and Classification NC H Cyanide OH Alcohol Q Identify the function group present in given molecule and encircle them: SH OHC O O 11.  thio alcohol SH OHC Sol aldehyde O ether O ketone Q Number of different functional group present in given compound N OCH3 N CH2 H CH2 CH2 NH2 N Cl C Cl H Sol Functional Groups and Classification Total 5 12.  Q Penicillin has following structure H H H N S O CH3 O N CH3 O COOH H Number of π-bonds possible in given structure 3 H Sol N H H S CH3 O O N CH3 1 O COOH 1 H 3 + 1 + 1 +1 = 6 1 Let’s understand Homologous Series A homologous series is a series of compounds having same functional group (thus having same chemical properties) and consecutive members have a difference of molecular mass ‘14’ or differ in Functional Groups and Classification molecular formula by –(CH2)– unit. Example-1 y CH4 Methane Homologous series of alkanes y CH3–CH3 Ethane (also known as paraffins). y CH3–CH2–CH3 Propane Each consecutive member differ y CH3–(CH2)2–CH3 Butane by –CH2– y CH3–(CH2)3–CH3 Pentane Example-2 y CH3–OH Methanol y CH3–CH2–OH Ethanol Homologous series y CH3–CH2–CH2–OH Propanol of alcohol. y CH3–(CH2)2–CH2–OH Butanol y CH3–(CH2)3–CH2–OH Pentanol 13.  Example-3 O y H–C–OH Methanoic acid O y CH3–C–OH Ethanoic acid O y CH3–CH2–C–OH Propanoic acid Homologous series of carboxylic acid. O y CH3–(CH2)2–C–OH Butanoic acid y Pentanoic acid Calculation of number of s bond and π bonds in Introduction the compound y The first bond formed by atom s bond : is always s bond. It is formed by axial overlapping. Single bonds Ex. C2H6 are always s bonds. Þ 7 s bonds p bond : Functional Groups and Classification Ex. C2H4 Introduction y If two atoms forms more than one bond between them except Þ 5 s bond the first bond, rest all are p bonds. They are formed by sideways overlapping 14. Q Find the number of bonds (s bond and p bond) in following compounds : H H or (i) H–C ≡ C – H (ii) H H N C C N (iii) C C (iv) N C C N Sol Compound s bond p bond (i) H–C ≡ C – H 3 2 (ii) 7 1 (iii) 9 9 (iv) 21 3 Q Number of π bonds present in given compound is Functional Groups and Classification CO2H Number of π bonds present in given compound is : Sol 3+2+2+1=8 15.  Classification of Organic Compounds Acyclic (open chain) Cyclic (Closed chain) Saturated Usaturated Homocyclic Hetrocyclic Alkane (CnH2n+2) Alkene Alkyne Alicyclic Aromatic n=1, 2, 3.... CnH2n CnH2n–2 (C=C) (C≡C) Benzenoid Non-Benzenoid Alicyclic Aromatic Functional Groups and Classification 16.  Nomenclature Mainly three systems are adopted for naming an Introduction organic compound (i) Common names or Trivial system Initially organic compounds are (ii) Derived system named on the basis of source (ii) IUPAC system or Jeneva system from which they were obtained for Some typical compounds in which Trivial System : common and trivial names are also differ. ORGANIC S. NO. TRIVIAL NAME SOURCE COMPOUND Obtained by destructive Wood spirit or 1 CH3OH distillation Methyl spirit of wood 2 NH2CONH2 Urea Obtained from urine Marsh gas It was produced in marshy 3 CH4 (fire damp) places Obtained from Acetum –i.e. 4 CH3COOH Vinegar Vinegar 5 Oxalic acid Obtained from oxalis plant Obtained from formicus [Red 6 HCOOH Formic acid ant] 7 Lactic acid Obtained from sour mild 8 Malic acid Obtained from apples 9 CH3CH2CH2COOH Butyric acid Obtained from butter Obtained from goats Nomenclature 10 CH3(CH2)4COOH Caproic acid 17.  S.NO. ORGANIC COMPOUND TRIVIAL NAME SOURCE (COMMON NAME) 1 CH4 Marsh gas Methane 2 CH3OH Wood spirit Methyl alcohol 3 CH3COOH Vinegar Acetic acid 4 Acetone Dimethyl ketone Derived System Definition y This system is reserved for the following nine y According to this system any homologous series. compound is given name according to the parent name of the homologous series. NAME OF HOMOLOGOUS STRUCTURE OF S. NO. DERIVED NAME SERIES GROUP 1 Alkane Methane 2 Alkene Ethylene >C=C< 3 Alkyne Acetylene –C≡C– 4 Alkanol Carbinol Nomenclature 5 Alkanal Acetaldehyde 18.  IUPAC system of Nomenclature Definition y International union of pure and applied chemistry. y According to IUPAC naming y IUPAC system for naming is something that is very of organic compounds have similar to addressing a person with his complete some standard process may be designation. called naming method in which anything about naming of molecule in a systematic way. ß ß ⇓ Dr. Abdul Kalam (Prefix) Main name Surname Secondary prefix y It defines substituent & position of substituent. y IUPAC considers following given groups as substituents : 1. –R Þ alkyl Examples : –CH3 Þ methyl –CH2CH3 Þ ethyl –CH2CH2CH3 Þ propyl –CH2CH2CH2CH3 Þ butyl –Ph Þ phenyl 2. –OR Þ alkoxy Examples : –OCH3 Þ methoxy –OC2H5 Þ ethoxy –OCH2CH2CH3 Þ propoxy –OPh Þ phenoxy 3. –X Þ Halo Examples : –F Þ Fluoro –Cl Þ Chloro –Br Þ Bromo Nomenclature –I Þ Iodo 4. –NO2 Þ Nitro 5. –NO Þ Nitroso 6. –N3 Þ Azido 19.  Primary prefix y A primary prefix is used simply to distinguish cyclic from acyclic compounds. y A primary prefix, cyclo is used immediately before the word root. y It defines nature of parent carbon chain. y Open chain (alicyclic) Þ y Closed chain (cyclic) Þ Cyclo y Bicyclic Þ Bicyclo y Spirane Þ Spiro Word Root y It is the basic unit of the name. It denotes the number of carbon atoms present in the principal chain (the longest possible continuous chain of carbon atoms including the functional group and based upon the common names of alkanes) of the organic molecules. According to number of carbon’s in parent C– chain. C1 → meth C11 → undec C2 → eth C12 → dodec C3 → prop C13 → tridec C4 → but : C5 → pent : C6 → hex C20 → eicos C7 → hept : C8 → oct : C9 → non : C10 → dec C100 → hect Primary Suffix y A primary suffix is always added to the word root to indicate whether the carbon chain is saturated or unsaturated. Nomenclature y The three basic primary suffixes are given below : 20.  S.NO. TYPE OF CARBON CHAIN PRIMARY SUFFIX GENERAL NAME 1 (a) Saturated -ane Alkane (b) Unsaturated with one 2 -ene Alkene double bond (c) Unsaturated with one 3 -yne Alkyne triple bond y If the parent carbon chain contain two, three or more double or triple bond, numerical prefix such as di (for two), tri (for three), tetra (for four) etc. are added to the primary suffix. For example. Nomenclature 21.  S.NO. TYPE OF CARBON CHAIN PRIMARY SUFFIX GENERAL NAME (a) Unsaturated with one double 1 -diene Alkadiene bond (b) Unsaturated with one triple 2 -diyne Alkadiyne bond Secondary Suffix y A secondary suffix is always added to the primary suffix to indicate the nature of the functional group present in the organic compounds. Secondary suffix of some important functional groups are given below : S.NO. CLASS OF ORGANIC COMPOUNDS FUNCTIONAL GROUP 1 Alcohols –OH 2 Aldehydes –CHO 3 Ketones >C=O 4 Carboxylic acids –COOH 5 Acid amides –CONH2 6 Acid chlorides –COX 7 Esters –COOR 8 Nitriles –CN 9 Thioalcohols –SH 10 Amines –NH2 Nomenclature Note : y We will discuss secondary suffix in `detail after mono functional group naming. 22.  Nomenclature of Alkane Steps in IUPAC Naming (A) Selection of parent chain (B) Numbering at parent chain Rule-1 : y Select the longest carbon chain containing maximum number of carbon and this longest carbon chain is also called parent carbon chain (PCC). y Longest carbon chain not always straight. Eg. : Rule-2 : y If two or more carbon chain contains same number of carbon then PCC is considered which has more number of substituents. Eg. : Rule-3 : y Numbering of parent carbon chain is done by lowest locant rule. Lowest Locant Rule : y According to this rule numbering is done in such a way so that substituent will get lowest number. Nomenclature Eg. : 23.  Note : y In IUPAC naming numbers of substituent will be separated by (,) comma and number & alphabet is separated by (‘–’) hyphen. y Rule-4 : y If two or more different substituents are present at parent carbon chain then numbering is done according to lowest locant rule while writing IUPAC name follow alphabetical order. Eg. : Rule-5 : If two or more similar substituents are present on parent carbon chain then use di, tri, tetra etc. before 2° prefix while writing IUPAC name but di, tri, tetra, etc. are not considered alphabetically. Eg. : (1) (2) (3) Rule-6 : y If two or more substituents are present on parent carbon chain and they get same number from either side during numbering then numbering is done by alphabetical order. Nomenclature Eg. : 24. Q 1. 2. 3. 4. 5. 6. 7. 8. Sol 1. 2. 2,2-dimethylpropane 3,3-diethylpentane 3. 4. 2,2,4-trimethylhexane 4-ethyl-3,3-dimethylhexane 5. 6. 5-bromo-2,3-dichlorohexane 3-chloro-4-ethylhexane 7. 8. Nomenclature 3,4-dimethylhexane 3-bromo-1-chloro-2-iodopentane 25.  Nomenclature of cyclic alkane Rule : y The cyclic structure or ring is considered as P.C.C. till the number of carbon in the ring is same or greater than number of carbon in chain. y Rest all rules are similar as nomenclature of alkane. Examples : 1. → 1-methylcyclohexane 2.  → 1-ethylcyclopropane ‘or’ ethylcyclopropane 3. → Propylcyclopropane 4. → 1-cyclopropylbutane 5. → 1-ethyl-1,2-dimethylhexane Nomenclature 26.  Nomenclature of Alkene & Alkyne Rule-1 : Parent carbon chain selection : y Select the longest carbon chain containing maximum number of multiple bonds. y If two chains having same number of multiple bonds then check maximum number of carbons to select parent carbon chain. y If multiple bonds & carbon both are same then see maximum number of substituent to select parent carbon chain. y Number of multiple bond > Number of carbon > Number of substituent (priority order) EXAMPLE-1 : EXAMPLE-2 : EXAMPLE-3 : Rule-2 : Numbering of parent carbon chain : Nomenclature of Alkene & Alkyne y While doing numbering in alkene and alkyne minimum number should be given to multiple bond. y If multiple bond getting same number from either side then give minimum number to substituent. y For numbering multiple bond priority is high compare to substituent 27.  Examples : 1. 2. 1-bromoprop-1-ene 3. 3-bromoprop-1-ene 4. 1-bromo-3-chloroprop-1-ene 5. 3-bromo-1-chloroprop-1-ene 6. 1-bromobut-2-ene Rule–3 : If two or more similar multiple bonds are present on PCC then use di, tri, tetra etc. before 1° suffix and before this di, tri, tetra etc. ‘a’ should be written. Examples : Nomenclature of Alkene & Alkyne 2 4 6 1. 1 Hepta-1,3-diene 3 5 7 1 2 3 4 5 2. CH2 = CH – CH2 – CH = CH2 Penta-1,4-diene Rule–4 : If in parent carbon chain alkene and alkyne both are present and they are getting same number from either side i.e. in between alkene and alkyne) then numbering is done from alkene side because alphabetically ene > yne. 28. Examples : 1 2 3 4 5 1. CH2 = CH – CH2 – C ≡ CH Pent-1-en-4-yne 1 2 3 4 5 6 7 2. CH3 – CH = CH – CH2 – C ≡ C – CH3 Hept-2-en-5-yne Q 1. 2. 3. 4. Cl CH2 5. 6. Br – C ≡ C – CH2 – CH3 7. CH3 – C ≡ C – CH2 – CH = CH2 Sol 1. 3-ethylhex-1-ene 2. 4-ethylhept-1-ene 3. 4-chlorobut-1-yne 4. Buta-1,3-diyne 5. 1-cyclopropyleth-1-ene 6. 1-bromobut-1-yne 7. Hex-1-en-4yne Nomenclature of cyclic alkene Nomenclature of Alkene & Alkyne Rule : All rules are similar to alkene & alkyne but during numbering 1 number is always given to alkene.     3-methylcyclohex-1-ene 29.  Br Q 1. 2 3. 4. Br Cl Cl Br 5. 6. Sol 1. 3,4-dimethylcyclobut-1-ene 2. 1,4-dimethylcyclobut-1-ene 3. 1-bromo-2-chlorocyclobut-1-ene 4. 3-bromo-6-chlorocyclohex-1-ene 5. 1-bromo-4-chlorocyclopenta-1,3-diene 6. 6-bromo-3-ethyl-3-methylcyclohex-1-ene Nomenclature of Alkene & Alkyne 30.  Nomenclature of Complex Locant Definition Complex locant is defined as which consist of substituent in substituent. S.NO. COMPLEX LOCANT COMMON NAME IUPAC NAME 1 Iso propyl 1-methyl ethyl 2 Sec-butyl 1-methyl propyl 3 Iso-butyl 2-methyl propyl 4 Iso-pentyl 3-methyl butyl Nomenclature of Complex Locant 5 Tert-butyl 1,1-dimethyl ethyl 6 Neo pentyl 2,2-dimethyl propyl 31.  NOTE : y Complex locant are written in square brackets [ ] y In complex locant di, tri, tetra etc. should be considered in alphabetical order. iso, neo, sec. are also considered in alphabetic order. y IUPAC name will be preferred over common name. y If two similar complex locant are present then use bis, tris, tetrakis etc. [di = bis, tri = tris, tetra = tetrakis] Examples : 5-[1,1-dimethylethyl]undecane 4,5-bis [1,1-dimethylethyl]nonane Q 1. 2. 3. 4. 5. 6. Nomenclature of Complex Locant 7. 8. 9. 10. 11. 12. 13. 14. 32.  Sol1. 5-[1-methylpropyl]nonane 2. 3,4-diethyl-2-methylhexane 3. 3-ethyl-2,2 dimethylhexane 4. 1-[1,1-dimethylethyl]cyclohexane 5. 1-[1-methylethyl]cyclohexane 6. 1-ethylcyclohexane 7. 1-ethyl-1-methylcyclohexane 8. 1-ethyl-3-methylcyclohexane 9. 1-[1-methylpropyl]cyclohexane 10. 1-[1-methylcyclopropyl]cyclohexane 11. 1-cyclopropyl-3[1-methylethyl]cyclohexane 12. 3-methyl-5-[1-methylethyl]-4-propyl-octane 13. 2,2,3-trimethyl-6[1-methylethyl]nonane 14. 2,2,3,7,8,8-hexamethylnonane Substitutent Consist of Multiple Bond 1. If substituent having double bond : 2° prefix / secondary prefix alkenyl Examples : (i) ethenyl (ii) – CH = CH – CH3 prop-1-enyl (iii) – CH2 – CH = CH2 prop-2-enyl (iv) cycloprop-2-enyl (v) cyclobut-1-enyl (vi) 4-ethenylhepta-1,6-diene 2. If substituent having triple bond : 2° prefix alkynyl Nomenclature of Complex Locant Examples : (i) – C CH ethynyl (ii) –C C – CH3 prop-1-ynyl (iii) –CH2 – C CH prop-2-ynyl (iv) 4-ethynylhepta-1,6-diene 3. If substituent attached to parent carbon chain by multiple bond : 2° prefix ⇒ alkylidene 33.  Examples : (i) = CH2 Methylene or methylidene only for this (ii) = CH–CH3 Ethylidene (iii) = CH–CH2–CH3 Propylidene (iv) Cyclopropylidene (v) Cyclobutylidene Example : 4-methylenehepta-1,6-diene ‘or’ 4-methylidenehepta-1,6-diene Note : 1. CH2=CH2   vinyl CH2 = CH – (vinylic carbon) 2. CH3–CH=CH2 allyl CH2=CH–CH2– (allylic carbon) 3. Example : Nomenclature of Complex Locant 4. Example : Q C3H6Br2, How many gem dibromide are possible and how many vicinal dibromide are possible ? H3C—CH—CH2 — — Sol Br Br  Geminal    Geminal   Vicinal 34. Nomenclature of Epoxy    2° prefix - epoxy Q 1. 2. 3. 4. 5. Sol 1. 1, 2-epoxyethane 2. 1, 2-epoxypropane 3. 2,3-epoxybutane 4. 2,4-epoxypentane 5. (2,3), (4,5)-diepoxyhexane Nomenclature of Complex Locant 35.  IUPAC Naming of Functional Groups IUPAC Naming of Functional Groups 1. Carboxilic Acid 2. Sulphonic Acid 3. Acid Anhydride 4. Ester 1. Nomenclature of Carboxylic Acid 2° suffix oic acid Q 1. H C OH 2. H3C C OH 3. O O COOH O OH 4. C H 5. 6. Cl3C C OH O O O H2C C OH 7. 1 Sol 1. H – C – OH Methanoic acid O IUPAC Naming of Functional Groups 2 1 2. CH3 – C – OH Ethanoic acid O 3. 2-methylbut-2-en-oic acid 4. 3[cycloprop-2-enyl]butanoic acid 36.  5. Penta-2,4-dienoic acid 2 1 6. CCl3 – C – OH 2,2,2-trichloroethanoic acid O 7. 2-[cyclohexa-1,3 dienyl]ethanoic acid Nomenclature of Dicarboxylic Acid General molecular formula : NÞ0 1 2 3 4 5 6 O M S G A P S Oxalic Malonic Succinic Glutaric Adipic Pimelic Suberic IUPAC Naming of Functional Groups acid acid acid acid acid acid acid Q 1. +2 & & 2+ 2. +2 & &+ &+ & 2+ 2 2 2 2 3. +2 & &+ &+ &+ & 2+ 2 2 4. +2 & &+ &+ &+ &+ &+ & 2+ 2 2 5. +2 & &+ &+ &+ &+ &+ & 2+ 2 2 37.  2 Sol 1 3 4 1. 2. HO – C – CH2 –CH 2 – C – OH O O Common name : Oxalic acid Common name : Succinic acid IUPAC name : Ethane-1,2-dioic acid IUPAC name : Butane-1,4-dioicacid 1 2 3 4 5 3. HO – C – CH2 –CH2 – CH2 – C – OH O O Common name : Glutaric acid IUPAC name : Pentane-1,5-dioic acid 1 2 3 4 5 6 7 4. HO – C – CH2 –CH2 – CH2 – CH2 – CH2 – C – OH O O Common name : Pimelic acid IUPAC name : Hetpane-1,7-dioic acid 1 2 3 4 5 6 7 8 5. HO – C – CH2 –CH2 – CH2– CH2 – CH2 – CH2 – C – OH O O Common name : Suberic acid IUPAC name : Octane-1,8-dioic acid 2. Nomenclature of Sulphonic Acid 2° suffix Sulphonic acid Q 1. 2. 3. IUPAC Naming of Functional Groups 4. 5. Sol 1. Propane-1-sulphonic acid 2. Butane-2-sulphonic acid 3. 3-bromobutane-2-sulphonic acid 38.  4. But-3-ene-1-sulphonic acid 5. Pent-1-en-4-yne-3-sulphonic acid 3. Nomenclature of Anhydride 2° suffix oic anhydride Examples : 1. 2. IUPAC Naming of Functional Groups Q 1. 2. +& & 2 & &+ &+ 2 2 O O O 3. 4. O O O O Br Cl O 5. O 39.  Sol 1. Methanoicanhydride 2. Ethanoicpropanoicanhydride 3. 2-methylpropanoic-prop-2-enoic anhydride 4. 2-bromoethanoic-2-chloroethanoic anhydride O 1 5. O Cyclohexane-1,2-dicarboxylic anhydride 2 O 4. Nomenclature of Ester 2° suffix oate IUPAC Naming of Functional Groups Q 1. 2. 3. 4. 5. 6. 7. 40.  Sol 1. Ethylpropanoate 2. Ethyl-2-bromopropanoate 3. Methylmethanoate 4. [1-chloroethenyl]-2-bromobutanoate 5. Cyclopropylpentanoate 6. Pent-3-enylethanoate IUPAC Naming of Functional Groups 7. 2-bromo-1-methyleth-1-eyl-2- chlorobutanoate  Priority List of Functional Group S.NO. FUNCTIONAL GROUP 2° PREFIX 2° SUFFIX 1 – COOH carboxylic acid oic acid 2 – SO3H sulpho sulphonic acid 41.  3 – oic anhydride Alkanoyl oxy or 4 oate alkoxy carbonyl 5 halo formyl oylhalide 6 carbamoyl amide 7 –C N cyano nitrile 8 isocyano isonitrile 9 –CHO 3 or 4 al 10 keto/oxo one IUPAC Naming of Functional Groups 11 –OH hydroxy ol sulphonyl/ 12 –SH thiol mercapto 13 –NH2 amino amine 14 epoxy – 42.  IUPAC Naming of Functional Groups Nomenclatue of Acid Halide Let’s understand 2° suffix : oyl halide 1. Acid Halide 2. Amide 3. Cyanide 4. Aldehyde 5. Ketone Q 1. 2. 3. 4. 5. 6. 7. 8. 1 Sol 1. H – C – Cl Methanoylchloride O 2. Ethanoylchloride 3. Prop-2-en-1-oylchloride 2 1 Cl 4. 3 Prop-2-yn-1-oylchloride IUPAC Naming of Functional Groups O 4 2 3 1 Cl 5. 5 Penta-2,4-dien-1-oylchloride O 6. 2-methylpropan-1-oylchloride 7. 2,2-dimethylpropan-1-oylchloride 43.  8. 3-cyclopropylpentan-1-oylchloride Nomenclatue of Amide 2° su x : amide Q 1. 2. 3. 4. 5. Sol 1. 2-bromo-N,N-dimethylpropanamide 2. Ethanamide IUPAC Naming of Functional Groups 3. N-ethylethanamide 4. N, 2-dibromopropanamide 5. N-bromo-N-chloropropanamide Nomenclature of Cyanide (R–CN) 2° su x nitrile 44.  Q 1. CH3 – C ≡ N 2. 3. 4. 5. CH2=CH–CN 6. 7. Sol 1. CH3 – C ≡ N Ethanenitrile 4 2 1 1 2. 5 3 Pentanenitrile 3. 2-ethylhexanenitrile 4.  2-ethylbut-3-ene-1-nitrile 5. Pent-4-en-2-yne-1-nitrile 6. 3-cyclopropylpentanenitrile IUPAC Naming of Functional Groups 7. 3-bromo-2-[1-chloroethenyl]-but-3-enenitrile Nomenclature of Aldehyde 2° suffix al 45.  H Q 1. CH3 – C – H 2. 3. O O 4. 5. 6. O CH2 C H 7. 8. 9. Sol 1. Ethanal 2. Methanal 3. Prop-2-en-1-al 4. But-2-en-1-al IUPAC Naming of Functional Groups 5. 2-ethylpent-1-al 6. 4-[cyclolprop-2-enyl]pentan-1-al 7. Pent-4-en-1-al 46.  O CH2 C H 8. 2 1  2-cyclopentylethan-1-al 9. Propan-1,3-dial Nomenclature of Ketone 2° suffix one Q 1. 2. 3. 4. 5. 6. 7. 8. Sol 1. Propan-2-one 2. Butan-2-one IUPAC Naming of Functional Groups 3. But-3-en-2-one 4. Pent-3-en-2-one 5.  2-bromo-4-chloropentan-3-one 6.  Cyclopenta-2,4-dien-1-one 47.  7. Butane-2,3-dione 8. Hept-3-en-2,6-dione  IUPAC Naming of Polyfunctional Groups Subjective Problems Q1 Write down the correct IUPAC name of given compound : Sol 3-carbamoyl-4-fluoro-2-methyl-5- nitrohex-5-enoylchloride  Q2 Write down the correct IUPAC name of given compound : C N IUPAC Naming of Functional Groups C N 6' 1 1' C N Sol 5' 1-[4’-isocyanocyclohexene]methanenitrile 2' C N 4'  3' 48. Q3 Write down the correct IUPAC name of given compound : Sol 5-bromo-3-methoxy-2-methylhepta-3,5-dienamide  Q4 Write down the correct IUPAC name of given compound : Sol 3’-carbamoyl-2-cyclobutenyl-4’- isocyanocyclohexanoylchloride IUPAC Naming of Functional Groups  Q5 Write down the correct IUPAC name of given compound : Sol 2-[2’-isocyanoethenyl]pent-2-en-4-ynenitrile  49.  Q6 Write down the correct IUPAC name of given compound : Sol 2-[2’-bromo-1’-cyano-3’-fluorocycloprop-2-enyl] ethanamide  IUPAC Naming of Functional Groups 50.  IUPAC Naming of Alcohol and Amine Nomenclatue of Alcohol (R–OH) Let’s understand Secondary suffix – ‘ol’ Rule-1 : IUPAC Naming of Select longest carbon chain containing 1. Alcohol 1. Functional group 2. Amine 2. Multiple bond 3. Locant / substituent Priority : (i) > (ii) > (iii) Rule-2 : While numbering, functional group is given more preference over multiple bonds. Priority : Functional group>Multiple bond > Substituents Q 1. OH 2. OH 3. 2+ 4. 5. 6. %U 7. 8. 9. IUPAC Naming of Alcohol and Amine 10. 11. 2+ Sol 1. 4-methylpentan-1-ol 2. 4-methylpentan-2-ol 3. Prop-2-ene-1-ol 51.  4. 3,3-dimethylbutan-1-ol 5. 5-bromocyclohex-2-en-1-ol 6. Ethan-1,2-diol 7. 4,4-dimethylpent-2-en-1-ol  8. But-2-en-2-ol 9. 4-cyclopropylpentan-2-ol IUPAC Naming of Alcohol and Amine 10. 4-bromopentan-2-ol 11. Cyclohexa-2,5-dien-1-ol 52. Nomenclature of Amine [R – NH2] 2° suffix amine Q 1. CH3 – NH2 2. 3. CH3 – NH – CH2 – CH3 4. 5. 6. 7. 8. 9. 10. Sol 1. CH3 –NH2 Methanamine 3 1 2 4 2. Butan-2-amine NH2 3. N-methylethanamine 4. N-ethyl-N-methylpropan-1-amine IUPAC Naming of Alcohol and Amine 5. But-3-en-2-amine 1 2 6. NH–CH 2 –CH3 N-ethylbutan-2-amine 3 4 7. N-ethyl-2-methylpropan-2-amine 53.  8. N-ethyl-N-methylbutan-2-amine 9. 2-methylpropan-2-amine 2 10. 1 NH2 Prop-2-en-1-amine 3 Q 1. 2. 2 3. 4. +2 5. 6. 7. 8. 9. 10. IUPAC Naming of Alcohol and Amine Sol 1. 3-chloro-5-cyano-4-oxoheptanoicacid 2. 2-hydroxypropanoicacid 3. Ethyl-3-oxobutanoate 54. 4. 5-hydroxycyclohex-2-en-1-one 5. 6-amino-5-carbamoylheptane-2-sulphonic acid 6. 4-methoxycarbonylbut-2-en-1-oic acid 7. 4-ethanoyloxybutanoic acid 8. 4-ethanoyloxy-2-methylbutanoic acid 9. 3-chloroformyl-2-methyl-4- [N-methylamino]pentanoic acid IUPAC Naming of Alcohol and Amine  10. 2-cyanoethanoic acid  55.  Subjective Problems Q1 Write the IUPAC name of given compound : O Sol 2 4 1 3 3-amino-1-hydroxypent-3-en-2-one 5 OH NH2 Q2 IUPAC name of given compound is a-bromo-b-chlorocyclohex-p-en-1,4-dione 2 &O %U 2 Find a + b + p = O 1 Cl Sol 6 2 5-bromo-2-chlorocyclohex-2-en-1,4-dione 5 3 a = 5, b = 2, p = 2 Br 4 \a+b+p=5+2+2=9 O IUPAC Naming of Alcohol and Amine Q Write down the correct IUPAC name of following compounds : 2 %U (I) (II) (III) +2 Sol (I) 2-oxopropanal 56.  (II) 3-ethyl-4-[N-methylamino]pentane O 1 Br 6 (III) 2 2-bromo-5-hydroxycyclohexa-2,5-dien-1-one 5 3 HO 4 Q Identify the principle functional group according to IUPAC priority table for following given compound. (I) (II) (III) (IV) Sol (I) Aldehyde (II) Carboxylic acid IUPAC Naming of Alcohol and Amine (III) Ketone (IV) Alcohol 57.  Q Which of the following compounds have main functional group alcohol ? 2 (I) (II) (III) 2+ (IV) (V) Sol Priority: \ III, V have main functional group alcohol. IUPAC Naming of Alcohol and Amine 58.  Specific Rule and Aromatic Compound Naming Introduction Specific Rule of 1993 In an unbranched alkane 3 or more than 3 carbon containing functional group are attached then alkane is considered as parent carbon chain. Q 1. 2. 3. 4. 5. 3 2 1 Sol 1. CH2 — CH — CH2 propane-1,2,3-tricarboxylic acid Specific Rule and Aromatic Compound Naming COOH COOH COOH 3 2 1 2. H2C – HC – CH2 propane-1,2,3-tricarbonitrile CN CN CN 1 CHO 3. 2 CHO propane-1,2,3-tricarbaldehyde 3 CHO O 1 C – OEt 4. triethylpropane-1,2,3-tricarboxylate 2 C – OEt O 3 C – OEt O 59.  1 OH 5. 2 OH propane-1,2,3-triol 3 OH Special Note Point to remember 1. Aldehyde 1. Carbaldehyde If carbon containing terminal 2. Carboxylic acid 2. Carboxylic acid functional group is present on 3. Acid Chloride 3. Carbonylchloride cyclic ring then ring is considered 4. Amide 4. Carboxamide as parent carbon chain and 5. Cyanide 5. Carbonitrile carbo word is introduced for that 6. Ester 6. Carboxylate functional group. 2 2 2 & + & 2+ & &O Q 1. 2. 3. 2 2 & 1+ &1 & 2 &+ 4. 5. 6. Specific Rule and Aromatic Compound Naming 7. 2 Sol 1. & + cyclohexanecarbaldehyde 2 & 2+ 2. cyclohexanecarboxylic acid 2 & &O 3. cyclohexanecarbonylchloride 60.  2 & 1+ 4. cyclohexanecarboxamide &1 5. cyclohexanecarbonitrile 2 & 2 &+ 6. methylcyclohexanecarboxylate O 7. CH2 – C – H 2-cyclopentylethanal 2 1 NOMENCLATURE OF AROMATIC COMPOUND 1. Simple Naming Point to remember Specific Rule and Aromatic Compound Naming Rule-1 : If pure alkane directly attached with benzene then consider benzene as parent chain and write as benzene only. Ethylbenzene Rule-2 : Point to remember If attached group on benzene is not pure alkane then benzene will be considered as substituent and 2° prefix phenyl is used for it. 61.  Cl OH Q 1. 2. 3. Cl