7 inch NO MENC L ATU R E. 2.5 inch. 2.5 inch. 2.5 inch

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1 7 inch.5 inch N MENC L ATU R E.5 inch.5 inch

2 I N D E X Topic Page No. RGANIC EMISTRY NMENCLATURE 1. Common Name 01. Derived System 14. Nomenclature of Saturated unbranched hydrocarbon 17 4 Nomenclature of Saturated branched hydrocarbon Nomenclature of Unsaturated unbranched hydrocarbon 6. Nomenclature of Unsaturated branched hydrocarbon 7. Nomenclature of Functional group compounds 6 8. Nomenclature of Polyfunctional group compounds 9. Nomenclature ofalicyclic/cyclic compounds Nomenclature of Bicyclo compounds Nomenclature of Spiro compounds 4 1. Exercise Exercise - 5 Exercise - 58 Exercise Answer Key Hints/Solution 64 NMENCLATURE

3 ACC- -NMENCLATURE 1 NMENCLATURE F RGANIC CMPUNDS Mainly three systems are adopted for naming an organic compound : (i) (ii) (iii) Common Names or Trivial System Derived System IUPAC system or Geneva System CMMN R TRIVIAL SYSTEM n the basis of Source Property Discovery Structure (i) n the basis of source from which they were obtained. S.No. rganic Trivial Name Source Compound 1. H Wood spirit or Methyl btained by destructive distillation spirit of wood.. NH CNH Urea btained from urine. 4 Marsh gas (fire damp) It was produced in marsh places. 4. CH Vinegar btained from Acetum - i.e. Vinegar 5. CH xalic acid btained from oxalis plant. CH 6. HCH Formic acid btained from formicus [Red ant] 7. CH Lactic acid btained from lactous (milk) H 8. CH Malic acid btain from Apple (H)CH 9 CH Butyric acid btained from butter. 10. ( ) 4 CH Caproic acid btained from goats. 11. C H 5 H Grain alcohol btained from barley.

4 ACC- -NMENCLATURE (ii) n the basis of property 1. Glucose - Sweet in test. Glycol - Sweet poisnous. Glycerol - Sweet (Glycus - Sweet) (iii) n the basis of discovery 1. RMgx (Grigard Reagent). R Zn (Frankland reagent) (iv) n the basis of structure S.No. No. of Carbon atom Word Root (i) 1C Meth (ii) C Eth (iii) C Prop (iv) 4C But (v) 5C Pent (vi) 6C Hex (vii) 7C Hept (viii) 8C ct (ix) 9C Non (x) 10C Dec Common Names for Hydrocarbon Derivatives S.No. Compound Name 1. R X Alkyl halide. R H Alkyl alcohol. R SH Alkyl thio alcohol 4. R NH Alkyl amine 5. R R Dialkyl ether 6. Dialkyl ketone 7. R NH R Dialkyl amine 8. Trialkyl amine 9. R R Alkyl alkyl ether 10. Alkyl alkyl ketone 11. R NH R Alkyl alkyl amine 1. Alkyl alkyl alkyl amine R is termed as alkyl - -)

5 ACC- -NMENCLATURE GRUPS Atom or a group of atoms which possess any free valency are called as Groups. If their are two structure of same molecular formula then some prefix (n, iso, neo) are used two differentiate them. Normal group : (a) It is represented by n. (b) Groups having no branch (Straight chain). (c) Free bond will come either on Ist carbon atom or on last carbon atom. n butyl n propyl Iso group : When one methyl group is attached to the second last carbon of the straight carbon chain is named as iso group. e.g. Exception : HC C H C H Isopropyl Isobutyl Isopentyl C C H C (i) Iso octyl (ii) Iso heptyl Neo group : (a) When two methyl groups on second last carbon of a straight carbon chain is attached to other four carbon atom group is named as neo group. (b) It is represented by following structure - (c) NTE : C C C C C for eg. C C C C C Neo pentyl There should be one 4 carbon and atleast three methyl group on 4 carbon. Amyl group : (ptically Active) = If all valency are attached to different atoms. H C Active amyl Secondary amyl Active secondary amyl Active iso secondary amyl

6 4 ACC- -NMENCLATURE Secondary group : (a) The carbon having free valency attached to two carbon is called secondary carbon. (b) It is represented by following structure. C CC C eg. (i) (ii) (secondary butyl) (secondary pentyl) Tertiary group : (a) The carbon having free valency attached to three other carbon. (b) It is represented by following structure - C C C C e.g. (i) C Alkyl group : (Tertiary butyl) C (Tertiary pentyl) When a hydrogen is removed from Alkane (saturated hydrocarbon) then alkyl group is formed. A bond is vacant on alkyl group on which any functional group may come. e.g. (i) 4 H Methane Methyl alkane (ii) H Ethane ethyl H Alkyl - (C n H n+ ) (C n H n+1 ) (iii) Propane H n-propyl iso-propyl (iv) H n-butane n-butyl Sec. Butyl (v) iso-butane H iso-butyl C tertiary-butyl

7 ACC- -NMENCLATURE 5 n-pentyl (vi) n-pentane H active secondary amyl CH 5 CH5 secondary amyl iso-pentyl C (vii) H tertiary-pentyl iso-pentane CH 5 active amyl Active isosecondary amyl (viii) H neo-pentane neo-pentyl Alkenyl group : alkene H Alkenyl - (C n H n ) (C n H n 1 ) = = = Vinyl Allyl Propenyl(1-propenyl) C Isopropenyl (1-methyl-1-ethenyl)

8 6 ACC- -NMENCLATURE Alkynyl group alkyne H Alkynyl - (C n H n ) (C n H n ) C C C C Ethynyl Propargyl (-propynyl) Propynyl (1-propynyl) Alkylidene group Alkylene group alkane alkane H Alkylidene - from same carbon H Alkylene - from different carbon Position of double bond : In an unsaturated hydrocarbon if the position of double bond is on I st or last carbon then it s prefix will be (alpha) if it is on nd carbon it is termed as (Beta) & the (gamma) & (delta) and so on. eg. H C = - butylene H C = - butylene H C = - butylene H C = or H C = (Both are same positions, propylene) HC C Isobutylene = - hexylene = - octylene CMMN NAMING F DIHALIDES (a) (b) When two same halogen atoms are attached to the same carbon such compounds are called Gemdihalides. Common names of such compounds are alkylidene halides eg. : Cl Cl Ethylidene chloride H Isobutylidene Iodide I I Exception : Methylidene halide (wrong) Methylene halide (right) X X

9 ACC- -NMENCLATURE 7 (c) When two same halogen atoms are attached to adjacent carbon, these are called as vicinal dihalides. Common names of such compounds are alkylene halide. eg Propylene Iodide Cl HC C Cl Isobutylene chloride (d) When two same halogen atoms are attached at the two ends of a carbon chain its common naming will be polymethylene halide. poly word indicates the number of groups Poly di tri tetra penta Hexa eg. Trimethylene Iodide Br Br Pentamethylene Bromide Exception : X dimethylene halide (wrong) X ethylene halide (right) CMMN - NAMING F DI-HYDRXY CMPUNDS (a) When two H groups are attached to adjacent carbon atoms they are termed as alkylene glycol. H H H C H Butylene glycol Active amylene glycol (b) When two H group are attached at the two ends of a carbon chain, these compounds are named as polymethylene glycol. Poly Number of groups. eg. : H H Tetra methylene glycol Exception : H Dimethylene glycol (wrong) H Ethylene glycol (right) H H Hexamethylene glycol

10 8 ACC- -NMENCLATURE PRBLEMS Make the structure of following organic compounds - 1. Isopropylidene Bromide. Active amylene Iodide. Isobutylene glycol 4. Isobutylene 5. Trimethylene glycol ANSWERS 1. C Br. Br C. H C H 4. HC C 5. H H CMMN-NAMING F THE FUNCTINAL GRUP HAVING CARBN (Common naming for Hydrocarbon derivatives) S.No. Functional group Suffix (i) (ii) C H -ic Acid -ic anhydride (iii) C R -ate (iv) (v) C NH C X -amide -yl halide (vi) C H -aldehyde (vii) C N -o-nitrile (viii) N C -o-isonitrile Prefix : 1 Carbon Form- Carbon Acet- Normal Carbon Propion- 4 Carbon Butyr Iso - 5 Carbon Valer C + (=) double bond = Acryl - 4 C + double bond = Croton-

11 ACC- -NMENCLATURE 9 eg. H C H C H Formaldehyde Acetic Acid C Cl Propionyl chloride C H Acetaldehyde C NH Isobutyramide NMENCLATURE F ESTER C R The group which is attached to the oxygen is written as alkyl & the remaining structure is named on the basis of Functional Group suffix. eg. (i) H C (ii) C H (iii) C H Methyl formate Methyl formate Acetic acid (iv) C (v) C (vi) C Methyl acetate Ethyl acetate Ethyl propionate (vii) C (viii) C Ethyl acrylate Methyl crotonate NMENCLATURE F ANHYDRIDE Rule : Add the total number of carbon atoms & divide it by, the substract will give you the number of C - atom. Now name it according to suffix use for anhydride. Total = Substract = Number of C atom 4 = Acetic anhydride 6 = Propionic anhydride

12 1 0 ACC- -NMENCLATURE If R R, You need not to find out substract. eg. Acetic propionic anhydride (right) Propionic Acetic anhydride (wrong) Divide it in two parts as above & name it by suffixing ic anhydride (alphabatically) eg. Butyric propionic anhydride Isobutyric Secondary valeric anhydride Acrylic anhydride SLVED EXAMPLE Q.1 Which of the following is not a neo structure: (A) C (B) C C C (C) (D) C C Ans. Sol. C A carbon must be attached with four carbons. Q. Acryl aldehyde is - (A) A saturated aldehyde (C) A polymer Ans. D Sol. = unsaturated aldehyde. (B) An alkene (D) An unsaturated aldehyde Q. The common name of the compound C (A) Divinyl ketone (B) Diallyl ketone (C) Both A and B (D) None Ans. A Sol. = is called as vinyl group. is -

13 ACC- -NMENCLATURE 1 1 Q.4 Common name of = CN is : (a) acrylonitrile (b) vinyl cyanide (c) allyl cyanide (d) allyl nitrile (A) a, b and d (B) a, and b (C) only b (D) a, b and c Ans. B Q.5 The number of possible alkyl groups of iso octane are - (A) 1 (B) (C) 5 (D) 6 Ans. B Sol. C C H = Q.6 Write the common names of the following compounds 1. CN.. F 4. Cl 5. H 6. C NH 7. = SH 8. NH 9. H 10. C SH 11. C NH 1. C Br ANSWERS 1. Ethyl cyanide. Isobutyl Iodide. Active amyl fluoride 4. Iso pentyl chloride 5. Active amyl alcohol 6. Tertiary hexyl amine 7. Vinyl thio alcohol 8. Active secondary amyl amine 9. Secondary amyl alcohol. 10. Neopentyl thio alcohol 11.Isopropenyl amine 1. Propargyl Bromide

14 1 ACC- -NMENCLATURE MCQ Q.1 Which of the following are secondary radicals : (a) C H CH5 (b) C (c) = (d) ( ) (A) a, b, c, (B) a, d, c (C) b, c, d (D) a, b, d Q. Common name of the structure H H (A) Ethylene Glycol (B) Ethene dialcohol (C) Glycerol (D) Ethylene alcohol Q. Common name of the compound C NH is - (A) Acetamide (B) Propionamide (C) Butyramide (D) Acetic amide Q.4 The structure of butenyl radical is : (A) C H CH5 (B) = (C) C (D) C Q.5 Which one is structure of Maleic acid (A) (C) H C C H H C C H H CH H CH Q.6 Common name of the structure (B) H CH CH H C C H (D) H C C H C is : (A) vinyl acetate (B) acryle acetate (C) methyl acrylate (D) Vinyl ethanoate Q.7 Which is the structural formula of isoprene (A) (C) C (B) C Cl C (D) =

15 ACC- -NMENCLATURE 1 Q.8 The number of gem dihalides possible with the molecular formula C H 4 X and C H 6 X is given by the set : (A) 1, (B), 1 (C), (D) 1, 1 Q.9 Common name of the compound C 6 H 5 (A) Anisole (B) Benzaldehyde (C) Salicylaldehyde (D) None of these ANSWERS Q.1(D) Q.(A) Q.(B) Q.4(B) Q.5(D) Q.6(A) Q.7(B) Q.8(A) Q.9(B) PRBLEMS Q.1 Write down the structures of the following - 1. Di allyl amine. Tri methyl amine. Di isobutyl ether 4. Di isopentyl ketone 5. Di Active amyl amine 6. Di normal propyl ether 7. Tri neopentyl amine Q. Write down the common names of the following : 1. C N C. C Cl. C NH Ans.(1) 1. = NH =. N.HC HC 5. NH 4.HC C C N C C Ans. () 1. Tertiary valero-isonitrile. Isobutyryl chloride. Secondary Valer amide

16 4 6 ACC- -NMENCLATURE EXERCISE-1 (Exercise for JEE Mains) [SINGLE CRRECT ICE TYPE] Q.1 The hybrid state of C-atoms which are attached to a single bond with each other in the following structure are : = C (A) sp, sp (B) sp, sp (C) sp, sp (D) sp, sp Q. In the compound HCC =, the C C bond is the type of : (A) sp sp (B) sp sp (C) sp sp (D) sp sp Q. The number of acetynilic bonds in the structure are : C C C N [ ] [ ] (A) (B) (C) 1 (D) 4 [ ] Q.4 Which of the following is the first member of ester homologous series? (A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D) Ethyl methanoate [ ] Q.5 Which of the following compound s prefix iso is not correct (A) Iso pentane (B) Iso Hexane (C) Iso butane (D) Iso octane [ ] Q.6 The group of heterocylic compounds is: (A) Phenol, Furane (B) Furane, Thiophene (C) Thiophene, Phenol (D) Furane,Aniline [ ] Q.7 The compound which has one isopropyl group is : (A),,,-tetramethyl pentane (B),-dimethyl pentane (C),,-trimethyl pentane (D) -methyl pentane [ ] Q.8 Asubstance containing an equal number of primary, secondary and tertiary carbon atoms is: (A) Mesityl xide (B) Mesitylene (C) Maleic acid (D) Malonic acid [ ] Q.9 How many secondary carbon atoms does methyl cyclopropane have? (A) Nine (B) ne (C) Two (D) Three [ ] Q.10 ( ) C = has the IUPAC name : (A), Dimethyl 1 butene (B), Dimethyl 1 butene (C), Dimethyl butene (D) 1, Dimethyl 1 propene [ ] Q.11 IUPAC name of = C is : (A) 1, 4 Hexenyne (B) 1 Hexen 5 yne (C) 1 Hexyne 5 ene (D) 1, 5 Hexyene [ ]

17 ACC- -NMENCLATURE 5 EXERCISE- (Exercise for JEE Advanced) [REASNING TYPE] (A) (B) (C) (D) These questions consists of two statements each, printed as Statement-Iand Statement-II. While answering these Questions you are required to choose any one of the following four responses. If both Statement-I & Statement-II are True & the Statement-II is a correct explanation of the Statement- I. If both Statement-I & Statement-II are True but Statement-II is not a correct explanation of the Statement-I. If Statement-I is True but the Statement-II is False. If Statement-I is False but the Statement-II is True. Q.1 Statement-I : Pentane and -methyl pentane are homolo-gues. Statement-II : Pentane is a straight-chain alkane, while -methyl pentane is a branched-chain alkane. [00116] Q. Statement-I : All the C atom o but--ene lie in one plane. Statement-II : Double-bond C atoms are sp -hybridised. [ ] Q. Statement-I : The IUPAC name of citric acid is -hydroxy-propane-1,, -tricarboxylic acid. HC CH CH H Citric acid Statement-II : When an unbranched C atom is directly linked to more than two like-functional groups, then it is named as a derivative of the parent alkane which does not include the C atoms of the functional groups. [001175] Q.4 Statement-I : Rochelle s salt is used as complexing agent in Tollens reagent. Statement-II : Sodium potassium salt of tartaric acid is known as Rochelle s salt. The IUPAC name of Rochelle s salt NaC H CK is sodium potassium -, -dihydroxy butane-1, 4-dioate. H [ ] Q.5 Statement-I : The IUPAC name of isoprene is -methyl buta-1, -diene. Statement-II : Isoprene unit is a monomer of natural rubber. [001187] [MULTIPLE CRRECT ICE TYPE] Q.6 Which of the following statements is/are wrong? (A) C n H n is the general formula of alkanes (B) In homologous series, all members have the same physical properties (C) IUPAC means International Union of Physics and Chemistry (D) Butane contains two 1º C atoms and ºC atom [001185]

18 5 8 ACC- -NMENCLATURE EXERCISE- (Miscellaneous Exercise) Q.1 [ ] Q. [001188] Q. [00115] Q.4 [ ] Q.5 [001165] Q.6 N H [ ] Q.7 H [001177] Q.8 [ ] Q.9 [001189] Q.10 [001154]

19 ACC- -NMENCLATURE 6 1 EXERCISE-4 SECTIN-A (IIT JEE Previous Year's Questions) Q.1 The IUPAC name of the compound having the formula is: HC C (A),,-trimethyl-1-propene (B) 1,1,1-trimethyl--propene (C),-dimethyl-1-butene (D),-dimethyl--butene [JEE 1984] [ ] Q. Write the IUPAC name of = CH [JEE 1986] [ ] Q. The IUPAC name of the compound = ( ) is: (A) 1,1-dimethyl--propene (B) -methyl-1-butene (C) -vinyl propane (D) None of the above [JEE 1987] [ ] Q.4 The number of sigma and pi-bonds in 1-butene -yne are: [JEE 1989] (A) 5 sigma and 5 pi (B) 7 sigma and pi (C) 8 sigma and pi (D) 6 sigma and 4 pi [ ] Q.5 Write I.U.P.A.C name of following: (a) Me = methyl group [JEE 1990] (b) HC N C H 5 [JEE 1991] [001100] Q.6 Write IUPAC name of succinic acid. [JEE 1994] [ ] Q.7 The IUPAC name of C 6 H 5 CCl is (A) Benzoyl chloride (B) Benzene chloro ketone (C) Benzene carbonyl chloride (D) Chloro phenyl ketone [JEE 006] [001100]

20 6 ACC- -NMENCLATURE Q.8 The IUPAC name of the following compound is [JEE 009] CN Br H (A) 4-Bromo--cyanophenol (C) -Cyano-4-hydroxybromobenzene (B) -Bromo-5-hydroxybenzonitrile (D) 6-Bromo--hydroxybenzonitrile [ ] Q.9 The correct structure of ethylenediaminetetraacetic acid (EDTA) is [IIT-JEE 010] HC (A) HC HC (B) HC N = N N N CH CH CH CH (C) HC N N HC CH CH CH (D) HC H N N H CH HC [ ] SECTIN-B (AIEEE Previous Year's Questions) Q.10 The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system of nomenclature is [AIEEE 008] (A) S H, CH, CNH, (B), CH, S H, CNH (C) CNH,, S H, CH (D) CH, S H, CNH, [ ]

21 ACC- -NMENCLATURE 6 EXERCISE-1 Q.1 (A) Q. (C) Q. (C) Q.4 (C) Q.5 (D) Q.6 (B) Q.7 (D) Q.8 (B) Q.9 (C) Q.10 (A) Q.11 (B) Q.1 (D) Q.1 (A) Q.14 (B) Q.15 (A) Q.16 (B) Q.17 (B) Q.18 (D) Q.19 (C) Q.0 (B) Q.1 (D) Q. (C) Q. (C) Q.4 (B) Q.5 (B) Q.6 (B) Q.7 (D) Q.8 (A) Q.9 (B) Q.0 (D) Q.1 (C) Q. (C) Q. (C) Q.4 (A) Q.5 (D) Q.6 (D) Q.7 (C) Q.8 (B) Q.9 (D) Q.40 (B) Q.41 (B) Q.4 (C) Q.4 (C) Q.44 (B) Q.45 (D) Q.46 (A) Q.47 (B) Q.48 (A) Q.49 (D) Q.50 (B) EXERCISE- Q.1 (B) Q. (A) Q. (A) Q.4 (B) Q.5 (B) Q.6 (A), (B), (C) Q.7 (A), (B), (C) Q.8 (A), (B), (C) Q.9 (C), (D) Q.10 (A), (B), (C), (D) Q.11 (A), (B), (C), (D) Q.1 (A), (B), (C), (D) Q.1 (A), (B), (D) Q.14 (A), (B), (C), (D) Q.15 (A), (B), (C), (D) Q.16 [(A) Q; (B) R; (C) S; (D) P] Q.17 [(A) R; (B) P; (C) S; (D) Q] Q.18 [(A) R, Q; (B) P; (C) S ] Q.19 [(A) Q, R; (B) R, S; (C) P ] Q.0 [(A) R; (B) S; (C) P; (D) Q; (E) U; (F) T] EXERCISE-4 SECTIN-A Q.1 (C) Q. (B) Q.4 (B) Q.7 (C) Q.8 (B) Q.9 (C) SECTIN-B Q.10 (D)

22 6 4 ACC- -NMENCLATURE EXERCISE-1 Q.1 H H H C = C sp sp C C H sp sp Q. HC C = Q. H C C C C = C N Acetynilic group Q.4 H C Q.5 C Not Iso group Iso Q.6 Furan S Thiophene Q.7 Q.9 º º IS group 1º º º C Q.8 º 1º 1º º º º º º 1º Q.10 H C C = 4 1 1º Carbon º Carbon º Carbon,-dimethyl-1-butene Q.11 HC = C Hexene-5-yne Q.1 HC = = C methyl--pentene Q.1 Compound having hetero -atom (as, N, S etc) in cycle are known as heterocyclic compound. Substituent (methyl) Substituent (ethyl) Substituent ( methyl) Substituent (ethyl) Q.15 HC C C = C Substituent (1-methylethyl), 5-diethyl-4,5-dimethyl -5-[1-methyl ethyl] hept--ene

23 ACC- -NMENCLATURE 6 5 Q.17 H C N = Ethyl Methyl Vinyl Q.18 H C = C Pent--ene-1-yne Q.19 HC C C C , 4-dimethylpent-1-yne 1 Q.1 H C H H H º 1º sp sp sp Q. HC C N * Q.5 º º º º º (Toluene) 1º C 1 º C 5 º C 1º NH Functional group Q.6 H C 1 1-Ethoxy-1-propanamine ( ) not 1-Amino-1-Ethyoxypropane ( ) Q.7 C Ethyl-4, 5-dimethyldecane Br H C Q.8 C H Br 6 Br Br Terminal gem dibromide C Br Non-terminalgem dibromide

24 7 inch.5 inch.5 inch.5 inch