Iit Chemistry

IIT CHEMISTRY

IUPAC NOMENCLATURE

Physical & Inorganic Organic Chemistry NV Sir VKP Sir B.Tech. IIT Delhi M.Sc. IT-BHU

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A-475 Indra vihar, kota Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) NUCLEON IIT-JEE CLASSES FOR IIT-JEE IUPAC NOMENCLATURE

Contents

Topic Page No.

Theory 01 - 04

Exercise - 1 05 - 23

Exercise - 2 24 - 35

Exercise - 3 35 - 36

Answer Key 37 - 42

Name : ______Contact No. ______

A - 475 Indra Vihar , Kota IUPAC NOMENCLATURE

KEY CONCEPTS

Classification of organic compounds

IUPAC Nomenclature : Groups : Atom or a group of atoms which possess any 'charge' on it or any 'free valency' are called as Groups. Alkyl group : When a hydrogen is removed from saturated hydrocarbon then alkyl group is formed. It is

represented by R & its general formula is CnH2n + 1. A bond is vacant on alkyl group on which any functional group may come.  CH4 H CH3 – Methyl

 CH3 – CH3 H CH3 – CH2 – Ethyl

(a) C3H7 has following two isomers

(i) Normal propyl CH3–CH2–CH2–

(ii) Isopropyl (1-methyl ethyl) CH 3–CH–

CH3

(b) C4H9 has following four structures :

(i) n-butyl H3C–CH2–CH2–CH2–

(ii) Iso butyl (2-methyl propyl) CH 3–CH–CH2–

CH3

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 1 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU (iii) Secondary butyl (1-methyl propyl) CH 3–CH2–CH–

CH3

(iv) Tertiary butyl (1,1-dimethyl ethyl) CH3–C–

CH3

Alkenyl group :

CH2 = CH – Ethenyl

CH2 = CH – CH2 – Propenyal

CH3 – CH = CH – Propenyl(1-propenyl)

CH 3–C=CH2 Isopropenyl (1-methyl-1-ethenyl) C

Alkynyl group : CH  C– Ethynyl

Retained Name : Normal group :

(a) It is represented by 'n'.

(b) Straight chain of carbon atom is known as normal group.

n-butyl C–C–C–C–

n-propyl C–C–C–

Iso group :

It is represented by following structure C–C– C Neo group : (a) When two methyl group are attached to second last carbon atom group is named as neo group. (b) It is represented by following structure -

For eg. Neo pentyl

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 2 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU ALLOTMENT OF IUPAC NOMENCLATURE Table : The Word Root of Unbranched Alkanes

Number of Name Carbon Atoms 1 Methane 2 Ethane 3 Propane 4 Butane 5 Pentane

6 Hexane 7 Heptane 8 Octane 9 Nonane 10 Decane

11 Undecane 12 Dodecane 13 Tridecane 14 Tetradecane 15 Pentadecane

16 Hexadecane 17 Heptadecane 18 Octadecane 19 Nonadecane

20 Eicosane 21 Heneicosane 22 Docosane 23 Tricosane 30 Triacontane

31 Hentriacontane 40 Tetracontane 50 Pentacontane 60 Hexacontane 70 Heptacontane

80 Octacontane 90 Nonacontane 100 Centane or Hectane

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 3 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU Rules for Naming the compound having poly functional groups : - If any organic compound possess more than one functional group, then functional group of highest priority is taken in longest chain along with maximum number of substituents. The priority order of the final groups is as under

Table : Functional Groups in decreasing order of seniority

Class Name Suffix Prefix + ammonio – – ammonium (R4N ) 1. Cations ------+ phosphonio – – phosphonium (R4P ) + sulphonio – – sulphonium (R3S )

2. R – COOH Alkanoic Acid – oic Acid (carboxylic acid) Carboxy

3. – sulphonic Acid sulpho R – SO3H Alkane sulphonic Acid

4. R – C – O – C – R Alkanoic Anhydride – anhydride ------|| || O O

5. R – COOR Alkyl Alkanoate – alkanoate (carboxylate) Alkoxy carbonyl

6. R – C – X – oyl halide (carbonyl halide) || Alkanoyl halide halo carbonyl O

7. R – C – NH 2 – amide (carboxamide) || Alkanamide Carbamoyl O – nitrile (carbonitrile) cyano 8. R – C  N Alkanenitrile

9. R – C – H Alkanal – al (carbaldehyde) formyl || O

10. R – C – R Alkanone – one Oxo / Keto || O

11. Alkanol R – OH – ol hydroxy

12. R – SH Alkanethiol – thiol mercapto

Alkanamine – amine amino 13. R – NH2

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 4 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU PART - I : SUBJECTIVE QUESTIONS

Section (A) : Fundamental of Organic Chemistry

A-1. Write the number of  and  bonds in the following molecules.

CH3

(a) (b) OH (c) NCH– 3

A-2. What is the nature of marked carbon atom in the following compounds.

(a) (b) (c)

A-3. Find the number of 1°, 2° & 3° hydrogen atoms in the following compounds

(a) (b) CH3–CH2–CH3 (c) CH3–CH2–CH2–CH3

A-4. Draw formulae for the first four members of each homologous series begining with the following.

(a) H–COOH (b) H–CH=CH2 (c)

A-5. Find the hybridization state of each carbon atoms in following compound.

CH2 = C = CH – CH2 – C  C – CH2 – NH2

A-6. Calculate the molecular weight of the lowest hydrocarbon which contains sp & sp2 hybridised carbon atoms only.

A-7 Write the total number of bonds in the following compounds.

(a) (b) (c)

Section (B) : Classification and General Rules of IUPAC Nomenclature

B-1. Classify the following compounds as homocyclic, heterocyclic, alicyclic, aromatic, saturated and unsaturated.

(a) (b) (c) (d)

B-2. Indicate the following as 1°, 2° and 3° amines.

CH3 NH N (a) (b) (c) (d) NCH– 3

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 5 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU B-3. Indicate the following as 1°, 2° and 3° alcohol.

(a) (b) (c)

B-4. Write the common name of the following alkyl groups.

(a) (b) (c)

(d) –CH2–CH3 (e) CH3–CH2–CH2– B-5. Write the priority order of given functional groups.

–COOH, –CN, –CHO, –OH, –COCH3, –NH2 Section (C) : IUPAC-Nomenclature of Alkane C-1. Write IUPAC name of the following compounds :

(a) (b) (c) (d)

C-2. Write IUPAC name of the following Me Me (i) Me (ii) Me

(iii) (iv)

C-3. Write the IUPAC name of following compounds

(i)

(ii)

C-4. Write IUPAC name of the following compounds:- (a)

(b)

(c)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 6 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU C-5. Write the correct IUPAC name of the following compounds.

CH3 | (i) (ii) CH3 — CH2 — CH2 — CH2 — CH2 — CH — C — CH2CH3 | | CH3 CH2 — CH2 — CH3

(iii)

Section (D) : IUPAC-Nomenclature of Alkene & Alkyne D-1. Write the general formula of alkenes. Give common and IUPAC names of first three members. D-2. Write the general formula of alkynes. Give common and IUPAC names of first three members. D-3. Write IUPAC name of the following :-

(i) (CH3)3 C – CH = CH2 (ii) CH2 = CH – CH = CH2

CH3 CH3 CH –CH –CH –C–CH –C=CH (iii) 3 2 2 2 2 (iv)

CH3

D-4. Write the IUPAC name of the following compounds:-

CH3 CH2 – CH 3 CH3 – – CH – CH – CH– – CH – CH – CH = C – CH (a) CH3 – CH2 – – CH = CH – CH2 – CH3 (b) 3 2 3 –

CH2 –

CH – CH3 –

CH3

D-5. Draw the bond line structures of the following compounds. (a) 2-Methylhept-3-ene (b) 2,6-Dimethylhepta-1, 5-diene D-6. Write IUPAC name of the following

(i) (ii) (iii)

D-7. Write the IUPAC name of the following compounds:-

(a) CH3 – – C  C – CH3 (b) (c)

D-8. Write IUPAC name of the following

(i) (ii) CH3–CH=CH–C  CH

(iii) CH  C–CH2–CH = CH2 (iv) CH2=CH–CC–CH3

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 7 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU Section (E) : IUPAC-Nomenclature of Cyclic Compounds

E-1. Write correct IUPAC name of the following

(i) (ii) (iii) (iv)

E-2. Write the correct IUPAC name of the following compounds.

(a) (b)

E-3. Write the correct IUPAC name of the following compounds.

CH3 CH (a) 3 (b) (c)

E-4. Write structures of the following IUPAC name. (i) 3-Methylcyclohexene (ii) 1, 3-Dicyclopentyl propane (iii) 1-Methyl-4-propylcyclohexane (iv) 2-Ethyl-1,1-dimethylcyclopentane E-5. Write the IUPAC name of the following

(i) (ii) (iii) (iv)

E-6. Write IUPAC names of the following hydrocarbon (use common naming for hydrocarbon groups.)

(a) (b) (c) (d)

E-7. Identify the parent chain in the following compounds as ring or side chain.

(a) (b) (c)

(d) (e) (f)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 8 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU Section (F) : IUPAC of Functional groups

F-1. Write the correct IUPAC name of the following compounds. CH = CH – COCH 3 OH OH

(a) (b) CH2 – CH – CH 2 – CH 3

F-2. Write the correct IUPAC name of the following compounds.

Cl CH3 F | | | (a) (b) CH3  CH  CH2  CH  CH  CH2  CH3 | Br

F-3. Write IUPAC names of following ethers :

(a) (b) (c) (d)

Section (G) : IUPAC of Functional groups ( )

G-1. Write the correct IUPAC name of the following compounds.

(a) (b) CH3  CH2  CH CH  CH  CH2  CHO | CH3

G-2. Write the structure of the following molecules : (a) 4-Formyl-2-oxocyclohexane-1-carboxylic acid. (b) 2-Cyano-3-oxopentanedioic acid (c) 3-Methyl-2-methylenebut-3-enoic acid (d) 5-Oxocyclohex-2-ene-1-carbonitrile

Section (H) : IUPAC of Functional groups ( )

H-1. Write IUPAC Name

(a) CH3 CH 2 – CH – C – OCH 3 (b) (c) –

CH2 –

CH3

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 9 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU H-2. Write IUPAC names of following compounds.

(a) (b)

Section (I) : IUPAC-Nomenclature of Aromatic compounds

I-1. Write IUPAC name of the following

(a) (b)

I-2. Write the correct IUPAC name of the following :

(a) (b)

Section (J) : Structural Isomerism J-1. Identify the relationship between the given compounds.

(a) and

(b) and

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 10 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU J-2. Identify the relationship among the following :

(a)

(b)

(c)

(d)

J-3. Identify the relationship between the given compounds.

(a) & (b) &

Section (K) : Number of Structural Isomers K-1. Write the total sum of degree of unsaturation (D.U.) of following compound.

K-2. How many number of all structurally isomeric dienes with molecular formula C5H8 are possible ?

K-3. How many esters are possible of formula C4H8O2? What is relation between them? PART - II : OBJECTIVE QUESTIONS * Marked Questions may have more than one correct option. Section (A) : Fundamental of Organic Chemistry A-1. Number of bonds in given compound is :

CH2=C=CH-CCH (A) 10 (B) 12 (C) 14 (D) 16

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 11 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU A-2. Number of 3º and 2º carbon atoms in the following compound are.

(A) 5, 6 (B) 5, 7 (C) 4, 6 (D) 6, 6

A-3. Molecular formula of naphthaquinone is

(A) C12H8O2 (B) C11H6O2 (C) C10H6O2 (D) C10H8O2

A-4.

In above compound total number of 2º hydrogen atoms are : (A) 3 (B) 18 (C) 6 (D) 9

A-5. An organic compound has molecular formula C9H18. It is a saturated hydrocarbon and its all hydrogen atoms are identical. Its structural formula can be :

(A) (B)

A-6.

Incorrect statement for the above structure :

(A) I, II & III have CnH2n-2 general formula (B) I , II & III have same empirical formula (C) I , II are identical and homologue of compound III. (D) I, II & III have same molecular formula Section (B) : Classification and General Rules of IUPAC Nomenclature

B-1. compound is :

(A) Alicyclic heterocyclic (B) Aromatic heterocyclic (C) Saturated heterocyclic (D) Unsaturated homocyclic

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 12 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU B-2. Which of the following is not an alicyclic compound ?

(A) (B) (C) (D) N | H

B-3. The saturated heterocyclic compound is :

(A) (B) (C) N (D) N.. | H

B-4. Which of the following has not bridgehead carbon :

(A) (B) (C) (D)

B-5. Which of the following compound is unsaturated hydrocarbon.

(A) (B) CH3–C  N (C) (D)

B-6. Which of the following is a correct priority order of functional groups?

(A)

(B)

(C)

(D)

Section (C) : IUPAC-Nomenclature of Alkane

C-1. The correct IUPAC name of the alkane is :

(A) 2-Ethyl-4-methylhexane (B) 5-Ethyl-3-methylhexane (C) 3,5-Dimethylheptane (D) 3,5-Dimethylhexane

C-2. The correct structure of 6-Ethyl-2,3,5-trimethylnonane is :

(A) (B)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 13 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU C-3. The correct IUPAC name of the following compound is :

(A) 1-Bromo-1-ethyl-2-fluoro-2-iodo-1-nitroethane. (B) 3-Bromo-4-fluoro-4-iodo-3-nitrobutane. (C) 2-Bromo-1-fluoro-1-iodo-2-nitrobutane. (D) 1-Fluoro-1-iodo-2-bromo-2-ethyl-2-nitroethane. C-4. A student named a certain compound as 2, 3-diethylbutane. its correct IUPAC names is (A) 2, 3-Dimethylhexane (B) 3, 4-Dimethylhexane (C) 2-Ethyl-3-methylpentane (D) 2-Ethylbutane

C-5. Which alkane would have only the primary and tertiary carbon ? (A) Pentane (B) 2-Methylbutane (C) 2, 2-Dimethylpropane (D) 2, 3-Dimethylbutane

C-6. The common and IUPAC names for the group, (CH3)2CHCH2–respectively are (A) Isobutyl, 2-methylpropyl (B) Isobutyl, 1-methylpropyl (C) tert-Butyl, 1, 1-dimethylethyl (D) sec-Butyl, 2-methylpropyl Section (D) : IUPAC-Nomenclature of Alkene & Alkyne D-1. Select the structure with correct numbering in the chain :

(A) (B)

D-2. The correct IUPAC name of the compound (A) 4-Ethylpent-1-ene (B) 2-Ethylpent-4-ene (C) 4-Methylhex-1-ene (D) 3-Methylhex-1-ene

D-3. The correct structure of 2-Ethyl-3-methylhexa-1,4-diene.

(A) (B) (C) (D)

D-4. The correct IUPAC name of the compound is – F I C

Cl C CH2

CH2 CH2 Br (A) 4-Bromo-1-chloro-2-fluoroiodomethylbutene (B) 4-Bromo-2-chloromethyl-1-fluoro-1-iodobut-1-ene (C) 2-(2-Bromoethyl)-3-chloro-1-fluoro-1-iodoprop-1-ene (D) 1-Bromo-3-chloromethyl-4-fluoro-4-iodobut-1-ene

D-5. Ethoxyethene is written as follows, H2C = CH – O – CH2 – CH3. The structure of 2-Chloro-1-ethoxyethene (incorrect name) with correct numbering will be

1 2 1 2 (A) H2C  CH –O– CH2 – CH2 Cl– (B) CH2  CH –O– CH – CH3 | Cl

2 1 1 2 (C) H2C  –O–C CH2 – CH2 Cl– (D) –Cl CH  CH –O– CH2 – CH3 | Cl

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 14 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU D-6. The correct IUPAC name of the given compound is

(A) 3–Chloro–1–fluoro–1–iodo–4–methoxybut–1–en–3–yne (B) 4–Methoxy–2–chloro–1–fluoro–1–iodobutenyne (C) 3–Chloro–4–fluoro–4–iodo–1–methoxybutenyne (D) 2–Chloro–1–fluoro–1–iodo–4–methoxybutenyne Section (E) : IUPAC-Nomenclature of Cyclic Compounds

E-1. In which of the following side chain (acyclic chain) is the main chain.

(A) (B)

E-2. In which of the following compound IUPAC numbering is correct :

(A) (B)

E-3. IUPAC name for is

(A) (1-Methylpropyl)cyclobutane (B) 2-(n-butyl)cyclobutane (C) 2-Cyclobutylbutane (D) 1-Cyclobutylbutane

E-4. The correct IUPAC name of is :

(A) 1-Cyclopentyl-1, 1-dimethylbutane (B) 2-Cyclopentyl-2-methylpentane (C) 2-Methyl-2-cyclopropylpentane (D) 1, 1-Dimethyl-1-cyclopentylbutane

E-5. In which of the following cyclic chain is the main chain ?

(A) (B) (C) (D)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 15 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU E-6. IUPAC name of the compound is

(A) 1-Cyclohexyl-3-methylpent-1-ene (B) 3-Methyl-5-cyclohexylpent-1-ene (C) 1-Cyclohexyl-3-ethylbut-1-ene (D) 1-Cyclohexyl-3,4-dimethylbut-1-ene

E-7. The correct IUPAC name of the compound

(A) 1-Ethenylcyclohexa-2, 4-diene (B) 5-Ethenylcyclohexa-1, 3-diene (C) 6-Ethenylcyclohexa-1, 3-diene (D) Cyclohexa-2, 4-dienylethene

Section (F) : IUPAC-Nomenclature of Functional groups

F-1. The IUPAC name of

Br | CH3  CH  CH2  CH2  CH2  C  CH3 is | | OH Br

(A) 6, 6-Dibromoheptan-2-ol (B) 2, 2-Dibromoheptan-6-ol (C) 6, 6-Dibromoheptan-2-al (D) None of these

F-2. The correct IUPAC name of the compound is :

(A) 6-Ethyl-1-methyl-4-oxohept-6-ene-1-sulphonic acid (B) 7-Ethyl-5-oxooct-7-ene-2-sulphonic acid (C) 2-Ethyl-7-sulphooct-1-ene-4-one (D) 7-Methylene-5-oxononane-2-sulphonic acid

F-3. The correct IUPAC name of the compound is :

(A) 4-Ethyl-3-methylnonane-2, 8- diol (B) 6-Ethyl-7-methylnonane-2, 8-diol (C) 5-Ethyl-1, 6, 7-trimethylheptane-1, 7-diol (D) 4-Ethyl-2-methylnonane-2, 7-diol

F-4. The correct structure of 6-Amino-4-hydroxycylohex-2-ene-1-sulphonic acid.

(A) (B)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 16 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU F-5. The correct IUPAC name of the compound is :

(A) 3-(1-Methylethenyl)-4-hydroxypentan-2-one (B) 3-(1-Hydroxyethyl)-4-methylpent-4-en-2-one (C) 3-(1-Hydroxymethyl)-4-methylenepentan-2-one (D) 3-(1-Oxoethyl)-4-methylpent-4-en-2-ol.

F-6. IUPAC name of the compound CH3  NH  CH  CH2  CH  CH3 is | | CH3 CH3 (A) 2-(N-methylamino)-4-methylpentane (B) N-Methyl-4-methylpentan-2-amine (C) 2-(N-methylamino)-3-isopropylpropane (D) 2-(N-methylamino)-1, 4, 4-trimethylbutane

Section (G) : IUPAC-Nomenclature of Functional groups ( )

G-1. The IUPAC name of the following compound is :

(A) 3-Methylbut-2-enoic acid (B) 3-Methylbut-3-enoic acid (C) 2-Methylbut-1-en-4-oic acid (D) 3-Methylenebutanoic acid

G-2. The IUPAC name of the following is :

CH3CH  CH  CH2  CH  CH2COOH | NH2 (A) 3-Aminohept-5-enoic acid (B) 5-Aminohex-2-enecarboxylic acid (C) 3-Aminohept-4-enoic acid (D) 5-Aminohept-2-enoic acid

G-3. is named as :

(A) 2, 3-Dimethylenebutanal (B) 3-Methyl-2-methylenebut-3-enone (C) 3-Methyl-2-methylenebut-3-enal (D) 2, 3-Dimethylenebutanone

G-4. The correct IUPAC name of compound is :

(A) 1-Chloropentane-1, 4-dione (B) 4-Chlorocarbonylbutan-2-one (C) 4-Oxopentanoyl chloride (D) 3-Oxobutanecarbonyl chloride

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 17 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU CH2  CHO | G-5. IUPAC name of the compound OHC  CH2  CH2  CH  CH2  CHO is (A) 4, 4-Di(formylmethyl) butanal (B) 2-(formylmethyl) butane-1, 4-dicarbaldehyde (C) Hexane-3-acetaldial (D) 3-(2-oxoethyl) hexanedial

G-6. The correct IUPAC name of following compound is

COOH

CH2 NH 2 (A) 4-Aminomethyl-3-hydroxycyclohex-5-ene-1-carboxylic acid (B) 2-Aminomethyl-5-carboxycyclohex-3-en-1-ol (C) 4-Aminomethyl-5-hydroxycyclohex-2-ene-1-carboxylic acid (D) 3-Hydroxy-4-aminomethylcyclohex-5-en-1-oic acid

Section (H) : IUPAC-Nomenclature of Functional groups ( )

H-1.

The IUPAC name of the compound is : (A) Propanoic anhydride (B) Dipropanoic anhydride (C) Ethoxy propanoic acid (D) 1-Oxopropyl propanoate H-2. The IUPAC name of the compound is :

(A) Cyclobutanedioic anhydride (B) Butanedicarboxylic anhydride (C) Cyclobutanedicarboxylic anhydride (D) Butanedioic anhydride H-3. The correct IUPAC name of following compound is

(A) Methyl -2-ethylpropanoate (B) Methyl butane-2-carboxylate (C) Methyl- 2-methylbutanoate (D) Methoxypentanone

H-4. The IUPAC name of is

(A) Ethoxymethanone (B) Ethyl 2-methylpropanoate (C) Ethoxypropanone (D) 2-Methylethoxypropanone

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 18 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU H-5. Ethyl ethanoyloxyethanoate is :

(A) CH2 (B) CH2 (C) CH2 (D) CH2

H-6. The IUPAC name of the compound is :

(A) N-Ethyl-2-ethylpropanamide (B) N-Ethyl-2-methylbutanamide (C) N-Ethyl-2-methylpropanecarboxamide (D) N-Ethyl-2-ethylethanecarboxamide

H-7. IUPAC name of the compound BrCH2  CH  CO  CH2  CH2CH3 is | CONH2 (A) 2-Bromomethyl-3-oxohexanamide (B) 1-Bromo-2-amido-3-oxohexane (C) 1-Bromo-2-amido-n-propylketone (D) 3-Bromo-2-proponyl-propanamide Section (I) : IUPAC-Nomenclature of Aromatic compounds I-1. The IUPAC name of the following compound is :

(A) 5-Bromo-3-hydroxybenzenecarbaldehyde (B) 3-Bromo-5-formylphenol (C) 3-Bromo-5-hydroxybenzenecarbaldehyde (D) 1-Bromo-3-formyl-5-hydroxybenzene I-2. The IUPAC name of the compound is :

(A) 2-Cyano-1-formylbenzene-4-carboxylic acid (B) 3-Cyano-4-formylbenzene-1-carboxylic acid (C) 4-Carboxy-2-cyanobenzene-1-carbaldehyde (D) 2-Formyl-5-carboxybenzene-1-carbonitrile

I-3. IUPAC name of

(A) 4-Chlorophenyl benzoate. (B) Phenyl-4-chlorobenzenecarboxylate. (C) Benzyl-4-chlorobenzenecarboxylate. (D) 4-Chloro diphenylcarboxylate. I-4. The correct IUPAC name of the compound.

(A) N–Formyl-4-chlorobenzenamine (B) N–Formyl-4-chloroaniline (C) N–(4-chlorophenyl)methanamide (D) N–(Parachlorophenyl)–N–formylaniline

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 19 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU I-5. IUPAC name of the compound is

(A) 2-Chlorocarbonyl ethylbenzenecarboxylate (B) 2-Carboxyethylbenzoyl chloride (C) Ethyl 2-(chlorocarbonyl)benzenecarboxylate (D) Ethyl 1-(chlorocarbonyl)benzenecarboxylate I-6. The correct IUPAC name of the compound

(A) 2-Phenoxycarbonylbenzenecarboxylic acid (B) Phenyl-2-carboxybenzenecarboxylate (C) 2-Benzoyloxybenzenecarboxylic acid (D) 2-Benzyloxycarbonylbenzenecarboxylic acid Section (J) : Structural Isomerism J-1. Isomers have essentially identical. (A) Structural formula (B) Chemical properties (C) Molecular formula (D) Physical properties J-2. Compound with same molecular formula but different structural formula are called. (A) Isomers (B) Isotopes (C) Isobars (D) Isoelectric J-3. Which compound is not the isomer of 3-Ethyl-2-methylpentane ? (A) (B)

J-4. What is the correct relationship between the following compounds ? , CH3  CH2  CH  CH2  CH3 CH3  CH2  CH2  CH2  CH2 | | CH3 CH3 (A) Chain isomers (B) Position isomers (C) Functional isomers (D) Identical

J-5. What is the relation between 3-Ethylpentane and 3-Methylhexane ? (A) Chain isomers (B) Position isomers (C) Functional isomers (D) Relation

CH CH CHO J-6. CH3 – CH2 – NH – CHO ; 3   | NH2 I II Which type of isomerism is observed between I and II. (A) Chain isomers (B) Position isomers (C) Functional isomers (D) Metamers J-7. Which of the following is a pair of metamers ?

(A) (B)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 20 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU J-8. The correct relationship among the following pairs of given compounds is

(I, II) (II, III) (A) Functional Isomers Metamers (B) Metamers Functional isomers (C) Metamers Metamers (D) Functional Isomers Functional isomers

J-9. Which of the given set of molecules have similar molecular formula : (A) Nonane,2-methylheptane (B) 3-Isopropylcyclopent-1-ene, 3-methylhexane (C) 3-Methylcyclopent-1-ene,penta-1,3-diene (D) Ethylcyclohexane, oct-2-ene J-10. Which amongs the following are not correctly matched.

(A) & CH2=CH–CH=C=CH–CH=CH2 are ring chain isomers.

(B) & are positional isomers.

(D) & are functional group isomers.

J-11. Molecular formula C4H10O represent (A) Two primary alcohol (B) One secondary alcohol (C) One tertiary alcohol (D) All of these Section (K) : Number of Structural Isomers

K-1. Degree of unsaturation in is

(A) 3 (B) 2 (C) 4 (D) 6. K-2. How many positional isomers are possible for dimethylcyclohexane. (A) 3 (B) 4 (C) 5 (D) 6

K-3. How many aromatic isomers are possible for trichlorobenzene (C6H3Cl3) ? (A) 2 (B) 3 (C) 4 (D) 5

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 21 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU K-4. The number of ether isomers represented by formula C4H10O is (only structural) (A) 4 (B) 3 (C) 2 (D) 1

K-5. Total number of 2° amine isomers of C4H11N would be (only structural) (A) 4 (B) 3 (C) 5 (D) 2

K-6. Find the number of total structurally isomeric 3° amides with molecular formula C5H11NO. (A) 4 (B) 3 (C) 2 (D) 5

K-7. How many structural isomers of all the tertiary alcohols with molecular formula C6H14O. (A) 2 (B) 3 (C) 4 (D) 5

K-8. The number of structural isomers for C5H10 is : (A) 8 (B) 6 (C) 9 (D) 10

PART - III : ASSERTION / REASONING

Each question has 5 choices (A), (B), (C), (D) and (E) out of which ONLY ONE is correct. (A) STATEMENT-1 is true, STATEMENT-2 is true and STATEMENT-2 is correct explanation for STATEMENT-1. (B) STATEMENT-1 is true, STATEMENT-2 is true and STATEMENT-2 is not correct explanation for STATEMENT-1. (C) STATEMENT-1 is true, STATEMENT-2 is false. (D) STATEMENT-1 is false, STATEMENT-2 is true. (E) Both STATEMENTS are false.

1. Statement-1 : The locant (2, 6, 7) is preferred over the locant (3, 4, 8). Statement-2 : The first term, i.e. 2 in the first set is lower than the first term, i.e. 3 in the second set.

 2. Statement-1 : The IUPAC name of CH3 CH = C H–C CH is pent-2-en-4-yne and not pent-3-en-1-yne Statement-2 : While deciding the locants for double bond and triple bonds, lowest locant rule for multiple bonds is followed.

CH3 3. Statement-1 : The correct IUPAC name for the compound, CH is (1-methylethyl) cyclopentane. CH3 Statement-2 : It is named as a derivative of cyclopentane because the number of carbon atoms in the ring is more than in the side chain.

H 4. Statement-1 : is called cyclohexane nitrile. CN Statement-2 : It contains six carbon atoms in the ring and –CN as the functional group.

5. Statement-1 : The IUPAC name for the compound C2 H 5 –C–CH 2 OH is 2-ethyl prop-2-en-1-ol

CH2

Statement-2 : Ethyl (C2H5–) rather than methylene (=CH2) is considered as the substituent group because 'e' of ethyl comes first in alphabetical order than 'm' of methylene.

6. Statement-1 : The IUPAC name of citric acid is 2-hydroxy propane 1,2,3,- tricarboxylic acid COOH

HOOC COOH OH Statement-2 : When an unbranched carbon chain is directly linked to more than two like functional groups, then it is named as derivative of parent alkane which does not include the C-atoms of the functional groups.

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 22 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 7. Statement-1 : The IUPAC name for the compound, OHC–CH2–CH2–COOH is butane -3-formyl-1-oic acid Statement-2 : COOH is considered as substituent group while CHO is considered as the principal functional group.

8. Statement-1 : The IUPAC name for the compound C6H5 COOCH2CH2COOH is 3-benzoyloxypropanoic acid.

Statement-2 : C6H5CH2O is called benzoyloxy group

9. Statement-1 : Pentane and 2-methyl pentane are homologues Statement-2 : Pentane is straight chain alkane, while 2-methyl pentane is a branched chain alkane.

10. Statement-1 : Butane and 2-methyl butane are chain isomers Statement-2 : Butane is a straight chain alkane while 2-methyl butane is a branched chain alkane.

11. Statement-1 : Neopentane is chain isomer of n-pentane.

Statement-2 : Molecular formula of neopentane and n-pentane is C5H12.

12. Statement-1 : Alkanes containing more than three carbon atoms exhibit chain isomerism Statement-2 : All the C-atoms in alkanes are sp2–hybridized

2 13. Statement-1 : All the carbon atoms in CH2=C=CH2 are sp hybridised. Statement-2 : All the C atoms have 3 sigma and 1  bond in the above compound.

14. Statement-1 : All the carbon atoms of but-2-ene lie in one plane. Statement-2 : Double bond carbon atoms are sp2-hybridized.

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 23 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU PART - I : SUBJECTIVE QUESTIONS

1. Find the number of 1º, 2º & 3º hydrogen atoms in the following compounds :

(a) (b) (c) (d)

2. Identify the following as bicyclo (bridgehead), spiro or isolated compounds.

(a) (b) (c) (d)

3. Identify the degree of functional groups in the given compound :

(a) (b)

4. There are two acyclic hydrocarbon with molecular formula C4H4. Draw them. 5. Write the common name of the following compounds :

6. Write the correct IUPAC name of the following hydrocarbon (alkyl) groups.

(a) (b) (c) (d)

7. Write IUPAC name of the following compounds.

Cl I CH2  CH2  Cl | | | (a) (b) CH  CH  CH  CH  CH Br  CH2  CH2  CH  CH  CH3 3 2 3 | CH3

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 24 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 8. Write IUPAC name of the following compounds.

(a) (b) (c) (d)

9. Write the IUPAC name of the following hydrocarbon groups.

CH3 | (a) –CH=CH (b) –CCH (c) (d) –CH –CH=CH 2 — C  CH2 2 2

10. Write the IUPAC name of the following hydrocarbon groups.

CH3 (a) =CH–CH3 (b) | (c) –CH2–CCH (d) –CH=CH–CCH  C  CH3

11. Write the structure of following IUPAC name : (a) 6-Chloro-4-ethyl-5-methylhept-5-en-1-yne (b) 3, 7-Dimethylocta-1, 3, 6-triene. (c) 2, 3, 3-Trimethylhepta-1,5-diene (d) 4, 8-Dimethylnona-3, 7-diene-1, 5-diyne 12. Write IUPAC names of following compounds.

(a) (b) (c) (d)

13. Write IUPAC names of the following.

(a) (b) (c) (d)

14 . Write structure of the given molecules (a) 1-Cyclobutylprop-1-ene (b) 3-Bromo-6-ethylcyclohexa-1, 4-diene (c) 3, 5-Dimethylcyclohex-1-ene (d) 2-Cyclobutyl-4-ethylhex-1-ene 15. Write the correct IUPAC name of the followings :

(a) (CH3)2 CHCH = CHCH2OH (b)

16. Write structure of the given molecules-7 (a) 3-Methoxy-5, 5-dimethylcyclohex-2-en-1-ol (b) 5–Methyl-2-(methylethyl) cyclohexan-1-amine (c) 2–Chloro–3–methylcyclohex–3–ene–1–thiol (d) 3 –Bromo– 4–methyl cyclopentan-1-one 17. Write correct IUPAC name of the following compounds

(a) (b)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 25 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 18. Write the correct IUPAC name of the following :

(a) (b)

OCH3 O | || (c) (d) CH3  CH2  CH  CH2  C  Cl

19. Write structure of the given molecules : (a) 4-Sulphopentanoic acid (b) 2-Amino-3-hydroxypropanoic acid (c) 3-Ethyl - 7 - methylocta - 2, 6 - dienal (d) 2, 2–Dimethyl– 4–oxopentanenitrile 20. Write IUPAC names of following compounds

(a) (b)

21. Write IUPAC names of following compounds.

(a) (b)

22. Write the correct IUPAC name of the following :

(a) (b) (c) (d)

23. Write structure of the given molecules : (a) 2, 4, 6-Trimethylbenzenecarbonyl chloride (b) 3-Mercaptobenzaldehyde (c) 3-Sulphobenzenecarboxylic acid (d) 4-Methylbenzenesulphonic acid

24. Identify the relationship between compound I, II and III.

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 26 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 25. Identify the relationship between the given compounds.

(a) and (b) and

26. What is the degree of unsaturation in a compound with molecular formula C9H6N4?

27. What is the number of all aldehydes (structurally isomeric) with molecular formula C5H10O ?

PART - II : OBJECTIVE QUESTIONS Single choice type

1. Which of the following is homologue of CH3 NH CH2 CH2 CH3

(A) CH3CH2NHCH2CH3 (B) CH3CH2CH2NH2 (C) CH3 –CH–NH 2 (D) CH3CH2NH–CH3

CH3

2. Number of 10, 20, 30 and 40C present in compound (A) are respectively

(A) 7, 4, 5 and 1 (B) 7, 3, 4 and 1 (C) 7, 3, 5 and 1 (D) 7, 4, 4, 1 3. An example of an alicyclic compound is (A) Benzene (B) Hexane (C) Cyclohexane (D) Furan. 4. Which of the following is not a cyclic compound ? (A) Anthracene (B) Pyrrole (C) Isobutylene (D) Phenol

5. IUPAC name of the compound is

(A) 2, 2, 5-Trimethyl-4-(1-methylpropyl) nonane (B) 4, 8, 8-Trimethyl-6-(1-methylpropyl) nonane (C) 3, 6-Dimethyl-4-(1-methylene tertiary butyl) nonane (D) 6, 6-Dimethyl-2-propyl-4-(1-methylpropyl) heptane

6. IUPAC nomenclature of the given organic compound will be : (CH3)2C(CH2CH3)CH2CH(Cl)CH3 : (A) 5-Chloro 3, 3-dimethyl hexane (B) 4-Chloro-2-ethyl-2-methyl pentane (C) 2-Chloro-4-ethyl-4-methyl pentane (D) 2-Chloro-4, 4-dimethyl hexane

7. In the structure of 4-Isopropyl-2,4,5-trimethylheptane, number of 10, 20 & 30 H’s are respectively. (A) 18, 5, 4 (B) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4 8. What is the correct IUPAC name of the incorrect name Hepta-1,4-dien-6-yne : (A) Hepta-3,6-dien-1-yne (B) Hepta-3,4-dien-1-yne (C) Hepta-3,5-dien-1-yne (D) Hept-3-yne-1,4-diene

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 27 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 9. IUPAC name of the compound CH2  CH  CH  C  CH2 is | | CH2CH3 Cl (A) 3-Ethyl-4-chloropenta-1, 4-diene (B) 2-Chloro-3-ethylpenta-1, 4-diene (C) 4-Chloroethenylpent-1-ene (D) 3-Ethenyl-4-chloropent-4-ene

10. The correct IUPAC name of is :

(A) 1, 4-Diethyl-2-methyl-5-propylcyclohexane (B) 1, 4-Diethyl-5-methyl-2-propylcyclohexane (C) 2, 5-Diethyl-1-methyl-4-propylcyclohexane (D) 2, 5-Diethyl-4-methyl-1-propylcyclohexane

11. The correct IUPAC numbering in the compound is :

(A) (B) (C) (D)

12. The correct IUPAC name of the compound :

(A) 1-Ethylidenecyclohex-2-ene (B) 3-Ethylidenecyclohex-1-ene (C) 2-Ethylidenecyclohex-1-ene (D) 3-Ethenylcyclohex-1-ene

13. The correct IUPAC numbering in the compound is :

(A) (B)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 28 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU O || 14. IUPAC name of the following compound CH3 – CH –C– CH –O– CH2 – CH3 is : | | OCH3 CH3 (A) 2-Ethoxy-4-methoxypentan-2-one. (B) 2-Ethoxy-4-methoxypentan-3-one. (C) 2-Ethoxy-3-methoxypentan-3-one. (D) None of the above

15. The correct structure of 3-Formyl-5-oxocyclohex-3-enecarbonyl chloride is :

(A) (B)

16. The IUPAC name of the compound is :

(A) Cyclobutenedioic anhydride (B) Butenedicarboxylic anhydride (C) Cyclobutenedicarboxylic anhydride (D) Butenedioic anhydride 17. The correct IUPAC name of the compound is :

(A) 1, 2, 3-Triaminobutane-1, 3-dione (B) 2, 4-Diamino-3-oxobutanamide (C) 1, 3-Dioxobutane-1, 2, 4-triamine (D) 1, 3, 4-Triaminobutane-2, 4-dione 18. IUPAC name of the following molecule is

COOH

Br COOH (A) 2-Bromobenzene-1,4-dioic acid (B) 3-Bromobenzene-1,4-dicarboxylic acid (C) 2-Bromobenzene-1,4-dicarboxylic acid (D) 3-Bromobenzene-1,6-dicarboxylic acid

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 29 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 19. IUPAC name of the following compound COOH

HO NO2 (A) 2-Bromo-5-hydroxy-3-nitro benzoic acid (B) 6-Bromo-5-nitro-3-hydroxy benzoic acid (C) 3-Nitro-2-bromo-5-hydroxy benzoic acid (D) 2-bromo-3-Nitro-5-hydroxy benzoic acid

20. ,

Relation between above compounds is: (A) Position isomers (B) Chain isomers (C) Identical (D) Functional isomers

21. Which type of isomerism is observed between I and II ?

CH3 – CH2 –C– OCH3 , || O (I) (II)

(A) Functional isomerism (B) Metamerism (C) Position isomerism (D) Stereoisomerism 22. Which one of the compound is not isomer of others ?

(A) (B) (C) (D)

23. Which type of isomerism is observed between I and II ?

(A) Functional isomerism (B) Metamerism (C) Chain isomerism (D) Position isomerism 24. Ethyl 3–(propanoyloxy)cyclopentanecarboxylate & Diethyl cyclopentane–1,2–dicarboxylate are (A) Chain isomers (B) Positional isomers (C) Metamers (D) Functional isomers 25. How many positional isomers are possible for 3–ethylpentane (including itself) (A) 1 (B) 2 (C) 3 (D) 4

26. The total number of unsaturated cyclic structure possible for a compound with the molecular formula C4H6 is: (A) 3 (B) 4 (C) 5 (D) 6 More than one choice type 27. All the members of a homologus series have same (A) Functional group (B) Empirical formula (C) General formula (D) All of these

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 30 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 28. The pair of compounds having the same general formula.

(A) and (B) and

29. Which functional groups are not present in given compound :

(A) Amide (B) Alcohol (C) Amine (D) Aldehyde

30. The compound with only primary hydrogen atoms is/are (A) Hexamethylcyclopropane (B) Neohexane (C) Tetramethylbutane (D) Hexamethylbenzene

31. Correct IUPAC names as per rules are (A) 1,1,1-Trichloro-2,2-diphenylethane (B) 3-Cyclopentylbut-1-ene (C) Cyclopenta-2,4-diene (D) 1-Bromo-2,3-dichlorocyclopropane 32. In which of the given molecules cyclic part is/are parent chain :

(A) (B)

33. Which of the following is/ are incorrect IUPAC name : -

(A) 2-Methylbutan -3-one

(B) 3-Ethenylpent-1-en-4-yne

CH3 (C) 3-(2-Aminoethyl)-2-methylcyclohexan-1-ol

CH2 CH 2 NH 2

(D) 4-Methyl-3-oxopentan-2-ol

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 31 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 34. Which is/are the correct IUPAC name of the corresponding structures OH

CH3 (A) 3-(N-Ethylamino)-2-methylcyclohexan-1-ol

NHCH2 CH 3

(B) 3-Bromo-2–chlorobutanal

CN | (C) CH2  CH  CH2  CH3 Methyl-3-cyanopentanoate | COOCH3

(D) Cyclohexanal

35. Which of the following IUPAC name are correct.

(A) 2-Methylcyclopentanecarboxamide.

(B) Cyclohexanoyl chloride.

(D) Methyl 2-bromocyclohexanecarboxylate

36. Which of the following pairs of structures represent the constitutional isomers ?

(A) CH2=CHCH2CH3 and

(B) CH3OCH2CH3 and

(D) CH2ClCHClCH2CHO and CHCl2CH=CH–CH2–OH 37. Which of the following is the correct relationship ? NH 2 NHCH CH – CH – NH CH – NHC H CH 3 2 2 2 2 2 5 CH3 3

CH3 CH3 CH3 CH3 I II III IV (A) I & II are functional isomers. (B) II & IV are metamers. (C) I & IV are position isomers. (D) I & III are chain isomers.

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 32 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 38. Which relationship is/are correct ?

(A) & Identical

Br Br Br Br (B) H & H Position isomer H H

H CH3 O (C) & Functional isomer COOH H

CH3 OC2 H 5

(D) C = C & Metamers H H

PART - III : MATCH THE COLUMN

1. Match the following : Column I Column II

(A) and (p) Homologs

(B) and (q) Functional isomers.

(D) and (s) Have same general formula

(t) Have same empirical formula.

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 33 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 2. Column – I Column – II

(A) and (p) Isomers

(B) and (q) Positional Isomers

(D) and (s) Homologues

PART - IV : COMPREHENSION

Comprehension # 1 (Questions 1 to 3) A saturated hydrocarbon (P) has six membered ring. Three alkyl groups attached to the ring alternate to each other. (i) First group has only two carbon atoms. (ii) Second group has four carbon atoms and its all hydrogen atoms are chemically same. (iii) Third group has total five carbon atoms. Its main chain contains three carbon atoms with ethyl as a substituent. 1. How many 3° hydrogen atoms are present in the hydrocarbon (P) ? (A) 2 (B) 3 (C) 4 (D) 5 2. How many 2º carbon present in the compound (P). (A) 10 (B) 12 (C) 6 (D) 8 3. IUPAC name of hydrocarbon (P) is (A) 1–(1–Ethylpropyl)–3–ethyl–5–(1,1–dimethylethyl)cyclohexane (B) 1–Ethyl–3–(1–ethylpropyl)–5–(1,1–dimethylethyl)cyclohexane. (C) 1–(1,1–Dimethylethyl)–3–ethyl–5–(1–ethylpropyl)cyclohexane (D) 1–(1,1–Dimethylethyl)–3–ethyl–5–(2–ethylpropyl)cyclohexane Comprehension # 2 (Questions 4 to 6)

There are three isomeric compounds P, Q, R with molecular formula C4H6O3. Compound P is a saturated hydroxy carboxylic acid compound Q is a symmetrical anhydride while R is an aldehydic ester.

4. Which of the following is P ?

(A) (B) (C) (D)

5. Which of the following is the metamer of Q ?

(A) (B) (C) (D)

6. Which of the following is R ?

(A) (B) (C) (D)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 34 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU PART - I : IIT-JEE PROBLEMS (LAST 10 YEARS)

* Marked Questions are more than one correct options. 1. Write IUPAC name of the following [IIT-JEE 2002]

2. Write IUPAC name of the following [IIT-JEE 2004]

3. Write IUPAC name of the following [IIT-JEE 2005]

4_ The IUPAC name of C6H5COCI is : [IIT-JEE-2006] (A) Benzoyl chloride (B) Benzene chloro ketone (C) Benzene carbonyl chloride (D) Chloro phenyl ketone

5. The number of structural isomers for C6H14 is : [IIT- JEE 2007] (A) 3 (B) 4 (C) 5 (D) 6 6. The IUPAC name of the following compound is : [IIT-JEE-2009]

(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile (C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile

7. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is / are : [IIT-JEE 2010]

8. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [IIT-JEE 2012] (A) sp and sp3 (B) sp and sp2 (C) only sp3 (D) sp2 and sp3 9. The carboxyl functional group (– COOH) is present in : [IIT-JEE 2012] (A) picric acid (B) barbituric acid (C) ascorbic acid (D) aspirin

10.* The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are : [JEE -2014] (A) tert-butanol and 2-methylpropan-2-ol (B) tert-butanol and 1,2-dimethylethan-1-ol (C) n-butanol and butan-1-ol (D) isobutyl alcohol and 2-methylpropan-1-ol

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 35 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 11. The IUPAC names(s) of the following compound is(are) [JEE (Ad.) -2017_P1]

(A) 4-methyalchlorobenzene (B) 4-chlorotence (C) 1-chloro-4-methylbenzene (D) 1-methyl-4-chlorobenzene

PART - II : AIEEE PROBLEMS (LAST 10 YEARS)

* Marked Questions are more than one correct options. 1. Which of the following compounds has wrong IUPAC name: [AIEEE- 2002]

(A) CH3–CH2–CH2–COO–CH2CH3  Ethyl butanoate (B)  3-Methylbutanal

(D)  2-Methyl-3-pentanone

2. The general formula CnH2nO2 could be for open chain [AIEEE- 2003] (A) diketones (B) carboxylic acids (C) diols (D) dialdehydes.

3. The IUPAC name of the compound is [AIEEE- 2004] HO (A) 3, 3 - dimethyl - 1 - hydroxy cyclohexane (B) 1, 1 - dimethyl - 3 -hydroxy cyclohexane (C) 3, 3 - dimethyl - 1 - cyclohexanol (D) 1, 1 - dimethyl - 3 - cyclohexanol 4. The IUPAC name of the compound shown below is [AIEEE 2006] Cl |

Br (A) 2 - Bromo-6-chlorocyclohex-1-ene (B) 6-Bromo-2-chlorocyclohexene (C) 3-Bromo-1-chlorocyclohex-1-ene (D) 1-Bromo-3-chlorocyclohexene

5. The IUPAC name of is : [AIEEE-2007, 3/120]

(A) 5, 5-Diethyl -4, 4-dimethylpentane (B) 3-Ethyl-4,4-dimethylheptane (C) 1, 1-Diethyl-2, 2-dimethylpentane (D) 4, 4-Dimethyl-5, 5-diethylpentane 6. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system of nomenclature is [AIEEE-2008, 3/105]

(A) –SO3H, –COOH, –CONH2, –CHO (B) –CHO, –COOH, –SO3H, –CONH2

(C) –CONH2, –CHO, –SO3H, –COOH (D) –COOH, –SO3H, –CONH2, –CHO 7. The IUPAC name of neopentane is : [AIEEE-2009, 4/144] (A) 2, 2-dimethylpropane (B) 2-methylpropane (C) 2, 2-dimethylbutane (D) 2-methylbutane 8. Aspirin is known as : [AIEEE 2012] (A) Acetyl salicylic acid (B) Phenyl salicylate (C) Acetyl salicylate (D) Methyl salicylic acid

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 36 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU EXERCISE - 1 PART - I

A-1. (a) 19  bonds, 6 bonds (b) 22  bonds (c) 20  bonds A-2. (a) 3° carbon (b) 2° carbon (c) 4° carbon

A-3. (a) 1° H  9, 3° H  1 (b) 1°H  6, 2°H  2 (c) 1°H  6, 2°H  4

A-4. (a) H–COOH, CH3–COOH, CH3–CH2–COOH , CH3–CH2–CH2–COOH

(b) CH2=CH2, CH3–CH=CH2, CH3–CH2–CH=CH2, CH3–CH2–CH2–CH = CH2

A-5.

A-6. H2C = C = CH2 M.W. = 40. A-7 (a) 24 (b) 20 (c) 19 B-1. (a) Homocyclic, alicyclic, saturated (b) Homocyclic, aromatic, unsaturated (c) Heterocyclic, alicyclic, saturated (d) unsaturated. B-2. (a) 2° (b) 2° (c) 3° (d) 3° B-3. (a) 2° (b) 3° (c) 1° B-4. (a) isopropyl group (b) sec-butyl group (c) Tert-butyl group (d) Ethyl group (e) n-propyl group B-5. Seniority order of functional groups :

–COOH > –CN > –CHO > > –OH > –NH2 C-1. (a) 2-Methyl propane (b) 2, 2-Dimethyl propane (c) 2-Methyl butane (d) 2, 2-Dimethyl butane

C-2. (i) (ii)

(iii) (iv)

C-3. (i) 2,2,3-Trimethylpentane (ii) 5-(1,2-Dimethylpropyl)nonane

C-4. (a) 5-Ethyl-3-methyloctane (b) 4-Ethyl-2,2,6-trimethylheptane (c) 3-Methylhexane

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 37 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU C-5. (i) 4-Ethyl-3, 7-dimethylnonane (ii) 4-Ethyl-4,5-dimethyldecane (iii) 4-(1,1-Dimethylethyl)-5-(1-methylethyl) octane

D-1. General formula  CnH2n

H2C = CH2 Ethylene Ethene

CH3–CH=CH2 Propylene Propene

CH3–CH2–CH=CH2 -Butylene 1-Butene

D-2. General formula  CnH2n–2 (1) CH  CH Acetylene Ethyne

(2) CH3–CCH Methyl acetylene (Allylene) Propyne

(3) CH3–CC–CH3 Dimethyl acetylene (Crotonylene) But-2-yne

D-3. (i) (ii)

(iii) (iv)

D-4. (a) 5-Methylhept-3-ene (b) 5-Ethyl-2,6-dimethyl-4-(3-methylbutyl)oct-2-ene

D-5. (a) (b)

1 2 3 4 5 D-6. (i) (ii) (iii) CH3 –C C–CH–CH 3

CH3 4-Methylpent-2-yne D-7. (a) 4-Methylpent-2-yne (b) 4-Propylhept-2-yne (c) 3,4,4-Trimethylhex-1-yne

D-8. (i) (ii)

(iii) (iv)

E-1. (i) (ii)

(iii) (iv)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 38 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU E-2. (a) 1, 3, 5 Trihexylcyclohexane (b) Cyclohexylcyclohexane (c) 3 – Cyclopropylprop – 1 – ene (d) 1–(Hex–3–enyl)cyclohex–1–ene E-3. (a) 1,5-Dimethylcyclopent-1-ene (b) 1-Cyclohexyl-4-cyclopropylbutane (c) 1-(1,1-Dimethylethyl)-2-(1-methylethyl) cyclopentane

E-4. (i) (ii) (iii) (iv)

1 2 E-5. (i) (ii)

1-cyclobutylethene

(iii) (iv)

E-6. (a) s-Butylcyclohexane (b) t-Butylcyclohexane (c) Isopropylcyclohexane (d) Neopentylcyclopentane E-7. (a) ring (b) side chain (c) ring (d) ring (e) side chain (f) side chain F-1. (a) 4 – Cyclohexylbut – 3 – en– 2-one (b) 2 – (2 – hydroxybutyl) cyclohexan – 1 – ol (c) 2-Methylpropan-2-ol (d) 3-Chlorobutan-1-ol

F-2. (a) 1-Chloro-5-methylhexan-2-one (b) 2-Bromo-2-chloro-5-fluoro-4-methylheptane (c) 2-Methoxy-N-methylethan-1-amine (d) 3-Bromo-2-chloro-5-methyloctane F-3. (a) Methoxyethane (b) Ethoxyethane (c) Epoxyethane (d) 1-chloro-2, 3-epoxypropane G-1. (a) 3-Methylbutanoic acid (b) 5-Methylhept-3-en-1-al. (c) 4-Oxopentanoyl chloride (d) 4-(But-2-enyl)non-6-enoic acid

G-2. (a) (b)

H-1. (a) Methyl-2-ethylbutanoate (b) Ethyl-3-methylpent-4-en-1-oate (c) 3,3 Dimethyl –2 – (1–methylethyl)butanamide H-2. (a) Ethanoic 2-methylpropanoic anhydride (b) Benzenecarboxylic anhydride (c) Pent-2-enedioic anhydride (d) Cyclohexane-1, 2-dicarboxylic anhydride

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 39 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU I-1. (a) Methylbenzene (b) Isopropylbenzene (c) Diphenylmethane (d) 1-Chloro-1-phenylethane. I-2. (a) Cyclohexylbenzene (b) 4-Bromo-3, 6-diphenyloctane (c) 1, 2-Dichloro-4-ethyl-5-nitrobenzene (d) 4-Chloro-1-nitro-2-propylbenzene J-1. (a) Chain Isomers (b) Functional isomers (c) Homologs. J-2. (a) I, II & III are functional isomers (b) I, & II are position isomers, (I or II) & III are functional isomers. (c) I, II & III are functional isomers (d) I & II are chain isomers, I & III are chain isomers and II & III are position isomers J-3. (a) Chain Isomers (b) Functional isomers (c) Metamers. (d) Position isomers K-1. 9 K-2. 6 K-3. 4, Metamers PART - II A-1. (B) A-2. (A) A-3. (C) A-4. (C) A-5. (B) A-6. (C) B-1. (A) B-2. (D) B-3. (C) B-4. (D) B-5. (D) B-6. (B) C-1. (C) C-2. (A) C-3. (C) C-4. (B) C-5. (D) C-6. (A) D-1. (D) D-2. (C) D-3. (C) D-4. (B) D-5. (D) D-6. (D) E-1. (C) E-2. (C) E-3. (A) E-4. (B) E-5. (B) E-6. (A) E-7. (B) F-1. (A) F-2. (B) F-3. (A) F-4. (B) F-5. (B) F-6. (B) G-1. (B) G-2. (A) G-3. (C) G-4. (C) G-5. (D) G-6. (C) H-1. (A) H-2. (D) H-3. (C) H-4. (B) H-5. (D) H-6. (B) H-7. (A) I-1. (C) I-2. (B) I-3. (B) I-4. (C) I-5. (C) I-6. (A) J-1. (C) J-2. (A) J-3. (B) J-4. (A) J-5. (A) J-6. (C) J-7. (B) J-8. (C) J-9. (D) J-10. (B) J-11. (D) K-1. (C) K-2. (B) K-3. (B) K-4. (B) K-5. (B) K-6. (D) K-7. (B) K-8. (D)

PART - III

1. (A) 2. (D) 3. (A) 4. (D) 5. (C)

6. (A) 7. (E) 8. (C) 9. (B) 10. (D)

11. (B) 12. (C) 13. (E) 14. (A)

EXERCISE - 2 PART - I 1. (a) (1°, 2°, 3°) H atoms = (9, 4, 1) (b) (1°, 2°, 3°) H atoms = (3, 10, 1) (c) (1°, 2°, 3°) H atoms = (6, 16, 0) (d) (1°, 2°, 3°) H atoms = (0, 18, 4) 2. (a) Bicyclo bridgehead (b) Bicyclo bridgehead (c) Isolated (d) Spiro 3. (a) 2° (b) 1° (c) 2° (d) 1°

4. H2C = C = C = CH2 & HC  C – C = CH2 5. (a) Isobutane (b) Neopentane (c) Isopentane (d) Neohexane 6. (a) 1-methylethyl (b) 1-methylpropyl (c) 1, 2-dimethylpropyl (d) 2, 3-dimethylbutyl 7. (a) 1-Bromo-3-chloro-4-methylpentane (b) 1-Chloro-3-ethyl-4-iodopentane (c) 4-Bromo-3-chloro-6-nitrooctane (d) 2-Bromo-2-chloro-5-fluoro-4-methylheptane

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 40 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 8. (a) Pent-2-ene (b) But-1-yne (c) 3-Methylbut-1-ene (d) 4–Ethyl–2–methylhex-1-ene 9. (a) ethenyl (b) ethynyl (c) 1-methylethenyl (d) prop-2-enyl 10. (a) ethylidene (b) 1-methylethylidene (c) prop-2-ynyl (d) but-1-en-3-ynyl

11. (a) (b)

12. (a) 3-Ethyl-1, 1-dimethylcyclohexane (b) 1-Ethyl-3-methyl-5-propylcyclohexane (c) 2-Bromo-1-chloro-4-fluorocyclohexane (d) 4-Bromo-1-chloro-2-fluorocyclohexane 13. (a) cyclohexylethene (b) 1-Ethylcyclohex-1-ene (c) 1-Ethenylcyclohex-1-ene (d) 1-cyclohex-1-enylbuta-1,3-diene

14 . (a) (b) (c) (d)

15. (a) 4-Methylpent-2-en-1-ol (b) 4, 5–Dimethylhex–5–ene–2–thiol (c) N,N-Dimethylpropan-2-amine (d) 1-Chloro - 4 - methylpentan - 2 - one

16. (a) (b) (c) (d)

17. (a) 3-propylpent-4-en-2-one (b) 3-Ethenylpentane-2,4-dione 18. (a) Pent–2–enoic acid (b) 3-Bromo-2-methylbutanal (c) 2, 4-Dimethylhex-2-enenitrile (d) 3-Methoxypentanoyl chloride

19. (a) (b)

20. (a) Methyl methanoate (b) 2-Ethoxycarbonylethanoic acid (c) Phenyl benzenecarboxylate (d) 2-Ethanoyloxy benzenecarboxylic acid 21. (a) 2-Methylpropanamide (b) N-Methylpropanamide (c) N, N-Dimethyl-2-methylpropanamide (d) N-Phenylbenzenecarboxamide 22. (a) 5-Formyl-2-nitrobenzoic acid (b) 4-Ethoxycarbonylbenzoic acid (c) 4-Nitroaniline (d) 3-Methylphenol

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 41 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU 23. (a) (b) (c) (d)

24. 1 & 2 are Position, 1 & 3 are Position, 2 & 3 are Position 25. (a) Metamers (b) Functional isomers (c) Chain isomers (d) position Isomers 26. 9 27. 4

PART - II

1. (D) 2. (C) 3. (C) 4. (C) 5. (A)

6. (D) 7. (B) 8. (A) 9. (B) 10. (A) 11. (D) 12. (B) 13. (B) 14. (B) 15. (A)

16. (D) 17. (B) 18. (C) 19. (A) 20. (C) 21. (A) 22. (D) 23. (B) 24. (C) 25. (A)

26. (B) 27. (A,C) 28. (A,B,D) 29. (C,D) 30. (A,C,D)

31. (A,B,D) 32. (A,D) 33. (A,B,D) 34. (A,B,C) 35. (A,C,D) 36. (A,C,D) 37. (A,B,D) 38. (A,B,C,D)

PART - III 1. (A – p,s), (B – q,s,t), (C – r,s,t), (D – q,s,t) 2. (A – p), (B – p,q), (C – p,r), (D – s).

PART - IV 1. (C) 2. (C) 3. (C) 4. (D) 5. (B) 6. (B)

EXERCISE - 3

PART - I 1. (4-Hydroxyphenyl) ethanal 2. 3-Aminobenzoic acid 3. 4-Methylbenzenesulphonic acid

4_ (C) 5. (C) 6. (B) 7. 5 8. (B)

9. (D) 10.* (ACD) 11. (B,C) PART - II 1. (C) 2. (B) 3. (C) 4. (C) 5. (B) 6. (D) 7. (A) 8. (A)

Physical & Inorganic By Organic Chemistry By A-475 Indra vihar, kota NV Sir VKP Sir IUPAC NOMENCLATURE # 42 Ph. - 8209916365 (NV Sir) 9057586906(VKP Sir) B.Tech. IIT Delhi M.Sc. IT-BHU