Contents · Contents Syllabus IUPAC Nomenclature & ... Rules for Naming the compound having poly functional groups : - If any organic compound possess more than one functional

Topic Page No.

Theory 01 - 07

Exercise - 1 08 - 23




Answer Key 32 - 33

Contents

Syllabus

IUPAC Nomenclature&

Structural Isomerism

Hybridisation of carbon; Sigma and pi-bonds; Shapes of simple organic molecules

& structural isomerism, IUPAC nomenclature of simple organic compounds (only

hydrocarbons, mono-functional and bi-functional compounds);

Name : ____________________________ Contact No. __________________

IUPAC NOMENCLATURE ANDSTRUCTURAL ISOMERISM # 1

A-479 Indra vihar, kotaPh. - 9982433693 (NV Sir) 9462729791(VKP Sir)

Physical & Inorganic By

NV SirB.Tech. IIT Delhi

Organic Chemistry By

VKP SirM.Sc. IT-BHU

IUPAC NOMENCLATURE & STRUCTURAL ISOMERISM

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 isrepresented by R & its general formula is CnH2n + 1. A bond is vacant on alkyl group on which any functionalgroup 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) CH3–CH–

CH3

(b) C4H9 has following four structures :

(i) n-butyl H3C–CH2–CH2–CH2–

(ii) Iso butyl (2-methyl propyl) CH3–CH–CH2–

CH3






VKP SirM.Sc. IT-BHU

(iii) Secondary butyl (1-methyl propyl) CH3–CH2–CH–

CH3

(iv) Tertiary butyl (1,1-dimethyl ethyl)

CH3

CH3–C–

CH3 Alkenyl group :

CH2 = CH – Ethenyl

CH2 = CH – CH2 – Propenyal

CH3 – CH = CH – Propenyl(1-propenyl)

CH3–C=CH2

C Isopropenyl (1-methyl-1-ethenyl)

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.

(c) Free bond will come either on 1st carbon atom or on last carbon atom.

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






VKP SirM.Sc. IT-BHU

ALLOTMENT OF IUPAC NOMENCLATURETable : The Word Root of Unbranched Alkanes

Number of Carbon Atoms Name

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






VKP SirM.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 priorityis taken in longest chain along with maximum number of substituents. The priority order of the final groupsis as under

Table : Functional Groups in decreasing order of seniority

IsomerismOrganic compounds having same molecular formula but differing from each other at least in some physical orchemical properties or both are known as isomers (Berzelius) and the phenomenon is known as isomerism.The difference in properties of isomers is due to the difference in the relative arrangements of various atomsor groups present in their molecules. Isomerism can be classified as follows:

Class

Cations

R – COOH

R – SO3H

R – C – O – C – R || || O O

R – COOR

R – C – X || O

R – C – NH2 || O

R – C N

R – C – H || O

R – C – R || O

R – OH

R – SH

R – NH2

Name

-------------------

Alkanoic Acid

Alkane sulphonic Acid

Alkanoic Anhydride

Alkyl Alkanoate

Alkanoyl halide

Alkanamide

Alkanenitrile

Alkanal

Alkanone

Alkanol

Alkanethiol

Alkanamine

Suffix

– ammonium (R4N+)

– phosphonium (R4P+)

– sulphonium (R3S+)

– oic Acid (carboxylic acid)

– sulphonic Acid

– anhydride

– alkanoate (carboxylate)

– oyl halide (carbonyl halide)

– amide (carboxamide)

– nitrile (carbonitrile)

– al (carbaldehyde)

– one

– ol

– thiol

– amine

Prefix

ammonio –phosphonio –sulphonio –

Carboxy

sulpho

------------

Alkoxy carbonyl

halo carbonyl

Carbamoyl

cyano

formyl

Oxo / Keto

hydroxy

mercapto

amino

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.






VKP SirM.Sc. IT-BHU

Constitutional or structural isomerism

(1) Chain, nuclear or skeleton isomerism : This type of isomerism arises due to the difference in the nature of the carbon chain ( i.e., straight or branched) which forms the nucleus of the molecule.

Examples :

(i) C4H10 : 3 2 2 3n Butane

CH CH CH CH

, 3 3|

Isobutane3

CH CH CHCH

(ii) C5H12 : (Three) 3 2 2 2 3n Pentane

CH CH CH CH CH

, 3 2 3|

Isopentane3

CH CH CH CHCH

, 3

|

3 3|

3Neopentane

CH

CH C CH

CH

Except alkynes chain isomerism is observed when the number of carbon atoms is four or more than four. Chain isomers differ in the nature of carbon chain, i.e., in the length of carbon chain. The isomers showing chain isomerism belong to the same homologous series, i .e., functional group,

c lass of the compound (Cyclic or open) remains unchanged. Chain and position isomerism cannot be possible together between two isomeric compounds. If two

compounds are chain isomers then these two wil l not be positional isomers.

(2) Position isomerism : It is due to the difference in the position of the substituent atom or group or an unsaturated linkage in the same carbon chain.

C3 H6 Cl2 : 3 2 32,2 Dichloro propane,(gemdihalide)

CH CCl CH , 3 2 2

1,1 Dichloro propane(gemdiha lide)

CH CH CHCl , 3 2| |

1,2 Dichloro propane(Vicdihalide)

CH CH CH

Cl Cl

, 2 2 2| |

1,3 Dichloro propane( , -dihali de)

CH CH CHCl Cl

Aldehydes, carboxylic acids (and their derivatives) and cyanides do not show position isomerism. Monosubsti tuted al icylic compounds and aromatic compounds do not show position isomerism. Structural isomers which differ in the position of the functional group are called regiomers.

For example, (i) 3 2 2CH CH CH OH (ii) 3 3CH CH CH|

OH






VKP SirM.Sc. IT-BHU

(3) Functional isomerism : This type of isomerism is due to difference in the nature of functional group present in the isomers. The following pairs of compounds always form functional isomers with each other.

Examples :

(i) Alcohols and ethers (Cn H2n+2O)

C2H6O : 3 2Ethyl alcoho l

CH CH OH ; 3 3Dimethyl ether

H C O CH

C3H8O : 3 2 2n propyl alcohol

CH CH CH OH

; 2 5 3Ethyl methyl ether

C H O CH

C4H10O : 3 2 2 2n Butyl alcohol

CH CH CH CH OH

; 2 5 2 5Diethyl ether

C H O C H

(ii) Aldehydes, ketones and unsaturated alcohols …etc. (Cn H2nO)

C3H6O : 3 2Propionaldehyde

CH CH CHO ; ||

3 3Acetone

O

CH C CH ; 2 3

1,2 Epoxy propane

CH CH CH

O

; 2 2Allyl alcohol

CH CH CH OH

(iii) Acids, esters and hydroxy carbonyl compounds …etc. (Cn H2nO2)

C2H4O2 : 3Acetic acid

CH COOH ; 3Methyl formate

HCOOCH

C3H6O2 : 3 2Prop ionic acid

CH CH COOH ; 3 3Methyl acetate

CH COOCH ; CH3 CH CHO

OH2-Hydroxypropanal

; ||

3 21 Hydroxy propan-2-one

O

CH C CH OH

(iv) Alkynes and alkadienes (Cn H2n-2) C4H6 : 3 2

1 ButyneCH CH C CH

; 2 2

1,3 ButadieneH C CH CH CH

; 3 3

2 ButyneCH C C CH

; 2 3

1,2 ButadieneH C C CH CH

(v) Nitro alkanes and alkyl nitrites ( 2NO and O N O )

C2H5NO2 : 2 5

Nitro ethane

OC H N

O ; 2 5

Ethyl ni triteC H O N O

(vi) Amines (Primary, secondary and tertiary)

C3H9N : 3 2 2 2Propan -1- amine

CH CH CH NH ; 3 2

3N Methyl ethanamine

HCH CH N

CH

;

3 3|

2Propan -2 - amine

CH CH CHNH

; 3

3 2

3N,N Dimethyl methanamine

CHCH CH N

CH

(vi i) Alcohols and phenols

C7H8O :

CH2OH

Benzyl alcohol

OH

CH3

o-Cresol

(vi ii) Oximes and amides

C2H5NO : 3Acetaldoxime

CH CH NOH ; ||

3 2Acetamide

OCH C NH






VKP SirM.Sc. IT-BHU

(4) Ring-chain isomerism : This type of isomerism is due to different modes of linking of carbon atoms, i.e.,the isomers possess either open chain or closed chain sturctures.

C6H12 :

CH2

CH2CH2

CH2CH2

CH2

Cyclohexane

; CH2

CH2 CH2

CH2CHCH3

Methylcyclopentane

; 3 2 2 2 21 Hexene

CH CH CH CH CH CH

Ring – chain isomers are always functional isomers.

(5) Metamerism : This type of isomerism is due to the difference in the nature of alkyl groups attached to the polyvalent atoms or functional group. Metamers always belong to the same homologous series. Compounds like ethers, thio-ethers ketones, secondary amines, etc. show metamerism.

(i) C5H13N : 33 7

3Dimethyl propyl amine

CHC H N

CH ; 2 5

2 53

Diethyl methyl amine

C HC H N

CH

(ii) C6H15N : 3 7 3 7Dipropyl amine

C H NH C H ; 2 5 4 9Butyl ethyl amine

C H NH C H

If same polyvalent functional group is there in two or more organic compounds, then chain or position isomerism is not possible, there will be metamerism e.g.,

(a) 3 2 2 3| |

(Pentan 2 one)

CH C CH CH CHO

; 3 2 2 3| |

(Pentan 3 one)

CH CH C CH CHO

are metamers and not position isomers.

(b) 3 2 2 3

(Pentan 2 one)

CH C CH CH CH| |O

; 3 3

3(3-Methylbutan-2-one)

CH C CH CH| | |

CHO

are metamers and not chain isomers.

Note : Alkenes donot show metamerism.






VKP SirM.Sc. IT-BHU

PART - I : OBJECTIVE QUESTIONS

* Marked Questions are having more than one correct option.

Section (A) : Fundamental of Organic Chemistry

A-1. In homologous series :(A) Molecular formula is same (B) Structural formula is same(C) Physical properties are same (D) General formula is same

A-2. How many secondary carbon atoms does methyl cyclopropane have?(A) None (B) One (C) Two (D) Three

A-3. Which of the following is the first member of ester homologous series ?(A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D)Ethyl methanoate

A-4. How many carbons are in simplest alkyne having two side chains ?(A) 5 (B) 6 (C) 7 (D) 8

A-5. How many 1º carbon atom will be present in a simplest hydrocarbon having two 3º & one 2º carbon atom?(A) 3 (B) 4 (C) 5 (D) 6

A-6.* The pair of compounds having the same general formula :

(A) and (B) and

(C) and (D) and H–CC–CC–H

A-7. (a) and (b)

True statement for the above compounds is:(A) (A) is phenol while (B) is alcohol (B) Both (A) and (B) are primary alcohol(C) (A) is primary and (B) is secondary alcohol (D) (A) is secondary and (B) is primary alcohol

A-8. The total number of secondary H-atoms in the structure given below are :(CH3)2CHCH2C2H5(A) 1 (B) 4 (C) 3 (D) 2

A-9. Which of the following is the triad of a homologous series -(A) CH3NH2, (CH3)2NH, (CH3)3 N (B) C2H5OH, (CH3)2CHOH, (CH3)3COH(C) Both the above (D) CH2 = CH2, CH3 – CH = CH2, C2H5 – CH = CH2

A-10. The homologue of phenol is -

(A)

CH OH2

(B)

OHCH3

(C)

OHOH

(D)

OH






VKP SirM.Sc. IT-BHU

A-11. What is not true about homologous series ?(A) All the members have similar chemical properties(B) They have identical physical properties(C) They can be represented by a general formula(D) Adjacent members differ in molecular mass by 14

A-12. An organic compound has molecular formula C9H18. It is a saturated hydrocarbon and its all hydrogenatoms are identical. Its structural formula can be :

(A) (B)

(C) (D)

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

B-1. C4H6O2 does not represent:(A) A diketone (B) A compound with two aldehyde(C) An alkenoic acid (D) An alkanoic acid

B-2. As per IUPAC rules, which one of the following groups, will be regarded as the principal functional group?

(A) –CC– (B) –OH (C)

O||

C (D)

O||

HC

B-3. The group of hetrocylic compounds is:(A) Phenol, Furane (B) Furane, Thiophene (C) Thiophene, Phenol (D) Furane, Aniline

B-4. Which of the following is a heterocyclic compound

(A) CHHC

|CHHC

(B)

COOHHC|

COOHHC

(C)

CHHC|

CHHC

(D)

CHHC|

CHHC

B-5. The number of sigma and pi-bonds in 1-butene 3-yne are:(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi (C) 8 sigma and 2 pi (D) 6 sigma and 4 pi

B-6. Which is an acyclic compound :(A) Methane (B) Benzene (C) Pyrrole (D) Cyclobutane

B-7. Which of the following is not an alicyclic compound ?

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






VKP SirM.Sc. IT-BHU

B-8. Which of the following has not bridgehead carbon :

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

B-9. Which of the following compounds is unsaturated hydrocarbon.

(A) (B) CH3–CN (C) (D)

Section (C) : IUPAC-Nomenclature of Alkane

C-1. The compound which has one isopropyl group is:(A) 2,2,3,3-tetramethyl pentane (B) 2,2-dimethyl pentane(C) 2,2,3-trimethyl pentane (D) 2-methyl pentane

C-2. The IUPAC name of the compound Br(Cl) IC. CF3 is:(A) 2-bromo-2-chloro-2-iodo1,1,1-trifluoroethane(B) 1,1,1-trifluoro-2-bromo-2-chloro-2-iodo ethane(C) 2-bromo-2-chloro-1,1,1-trifluoro-2-iodo ethane(D) 1-bromo-1-chloro-1-iodo-2,2,2-trifloro ethane

C-3. The IUPAC name of the following structure is [CH3CH(CH3)]2 C(CH2CH3)C(CH3) C(CH2CH3)2(A) 3,5-diethyl-4,6-dimethyl-5-[1-methylethyl]-3-heptene(B) 3,5-diethyl-5-isopropyl-4,6-dimethyl-2-heptene(C) 3,5-diethyl-5-propyl-4,6-dimethyl-3-heptene(D) None of these

C-4. The IUPAC name of this compound is :

(A) 2-fluoro-4-chloro-2,4-diethyl pentane

(B) 3-fluoro-5-chloro-3-methyl-5-ethyl hexane 3232

323

CHCH CHCH | |

CHCCHCCH| | Cl F

(C) 3-chloro-5-fluoro-3,5-dimethyl heptane

(D) 3,5-dimethyl-5-fluoro-3-chloro heptane

C-5. The IUPAC name of is -

(A) 2-bromo-4-isopropylpentane (B) 2, 3-dimethyl-5-bromohexane(C) 2-bromo-4, 5-dimethylhexane (D) 5-bromo-2, 3-dimethylhexane

C-6. Give the IUPAC name of

3

3

322223

33

3

CH|

CHCH|

CHCHCHCHCHCHCHCH|

CHCCH|CH

(A) 4-isopropyl-5-ter. butyl octane (B) 4-ter. butyl-5-isopropyl octane(C) 2-methyl-3-propyl-4-ter. butyl heptane (D) 2, 2-dimethyl-3-propyl-4-isopropyl heptane

C-7. Which alkane would have only the primary and tertiary carbon ?(A) Pentane (B) 2-Methylbutane(C) 2, 2-Dimethylpropane (D) 2, 3-Dimethylbutane

C-8. In the structure of 4-Isopropyl-2, 4, 5-trimethylheptane, number of 1°, 2° & 3° H's are respectively :(A) 18, 5, 4 (B) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4






VKP SirM.Sc. IT-BHU

Section (D) : IUPAC-Nomenclature of Alkene & Alkyne

D-1. The IUPAC name of the compound having the formula is:

3

23

3

CH|

CHCHCCH|CH

(A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene(C) 3,3-dimethyl-1-butene (D) 2,2-dimethyl-3-butene

D-2. The IUPAC name of the compound CH2=CH–CH(CH3)2 is:

(A) 1,1-dimethyl-2-propene (B) 3-methyl-1-butene

(C) 2-vinyl propane (D) None of the above

D-3. The correct IUPAC name of the compound :

(A) 5-ethyl-3, 6-dimethyl non-3-ene (B) 5-ethyl-4, 7-dimethyl non-3-ene(C) 4-methyl-5, 7-diethyl oct-2-ene (D) 2,4-ethyl-5-methyl oct-2-ene

D-4. The correct IUPAC name of :

3 3

2 5 2 5

CH – C C – CH| |C H C H

(A) 1, 2-diethyl butane (B) 2-ethyl 3-methylpentane(C) 3, 4-dimethyl-3-hexene (D) none is correct

D-5. The IUPAC name of the compound CH3CH = CHCH=CHCCCH3 is:(A) 4,6-octadiene-2-yne (B) 2,4-octadiene-6-yne(C) 2-octyn-4,6-diene (D) 6-octyn-2,4-diene

D-6. The correct IUPAC name of 2-ethyl-3-pentyne is:(A) 3-methyl hexyne-4 (B) 4-ethyl pentyne-2 (C) 4-methyl hexyne-2 (D) None of these

D-7. The molecular formula of the first member of the family of alkenynes and its name is given by the set(A) C3H2, alkene (B) C5H6, 1-penten-3-yne(C) C6H8, 1-hexen-5-yne (D) C4H4, butenyne

D-8. The IUPAC name of is -

(A) 2-ethyl-3-methyl-1-penten-4-yne (B) 2-ethyl-3-methyl-4-pentyn-1-ene(C) 4-ethyl-3-methyl-1-pentyn-4-ene (D) 4-ethyl-3-ethyl-4-penten-1-yne

D-9. The IUPAC name of

CH CH

HC C C C C CH CH

3

2 3

|| is :

(A) 5-ethyl- 5-heptene-1, 3- diyne (B) 3-ethyl- 2-heptene-4, 6- diyne(C) 5-ethenyl-1, 3- heptatriyne (D) 3-ethenyl-4, 6-heptatriyne






VKP SirM.Sc. IT-BHU

D-10.

The IUPAC name of the above structure is :(A) 2, 4, 5 - Triethyl-3-nonene (B) 5, 6 - Diethyl -3- methyl -4-decene(C) 2, 4, 5 - Triethyl -3- octene (D) 3 - Heptyl - 5- methyl-3- heptene

D-11. IUPAC name of the compound is :

(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

Section (E) : IUPAC-Nomenclature of Cyclic Compounds

E-1. The IUPAC name of the compound is -

(A) 1-chloro-2-bromocylohexane (B) 1, 2-bromochlorocyclohexane(C) 4-bromo-3-chlorocyclohexane (D) 1-bromo-2-chlorocyclohexane

E-2. The IUPAC name of the given compound

is -

(A) Octylcyclopentane (B) 3-cyclopentyloctane(C) cyclopentaneoctane (D) 6-cyclopentyloctane

E-3. The IUPAC name of

3

32

CH|

CHCHCHCHCH is:

(A) 1-cyclohexyl-3-methyl-1-pentene (B) 3-methyl-5-cyclohexyl-pent-ene(C) 1-cyclohexyl-3-ethyl-but-1-ene (D) 1-cyclohexyl-3,4-dimethyl-but-1-ene

E-4. The correct IUPAC name for the compound

C2H5 CH3

is -

(A) 6-Ethyl-1-methylcyclohex-1-ene (B) 3-Ethyl-2-methylcyclohex-1-ene(C) 1-Ethyl-2-methylcyclohex-2-ene (D) 2-Ethyl-1-methylcyclohex-1-ene

E-5. The name of the compound is -

(A) bicyclo [2.2.1] octane (B) bicyclo [1.1.1] octane(C) 1, 4-bismethylenecyclohexane (D) bicyclo [2.2.2] octane






VKP SirM.Sc. IT-BHU

E-6. Which of the following structures represents bicyclo [3.2.0] heptane -

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

E-7. The IUPAC name of compound is -

(A) Bicyclo [2.2.1] hept-2-ene (B) Bicyclo [2.2.1] hept-5-ene(C) Bicyclo [2.1.2] hept-2-ene (D) Bicyclo [1.2.2] hept-2-ene

E-8. The IUPAC name of compound is -

(A) Spiro [5.3] nonane (B) Spiro [3.5] nonane (C) Spiro [5.4] nonane (D) Spiro [4.5] nonane

E-9. The IUPAC name of is -

(A) 3-cyclopropyl-3-ethyl-2-propene (B) 1-cyclopropyl-1-ethylpropene(C) 3-cyclopropyl-2-pentene (D) (1-ethyl-1-propenyl) cyclopropane

E-10. The IUPAC name of is -

(A) 3-cyclobutylcyclopropane (B) 1-cyclopropyl-3-methylcyclobutane(C) 1, 3-cyclopropylmethylcyclobutane (D) 2-methylbicyclo [4.3.0] heptane

E-11. IUPAC name for is :

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

E-12. 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






VKP SirM.Sc. IT-BHU

E-13. The correct IUPAC name of the compound

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

Section (F) : IUPAC-Nomenclature of Functional I groups

F-1. The IUPAC name of the compound

OHOHOH|||CHCHCH 22 is:

(A) 1,2,3-tri hydroxy propane (B) 3-hydroxy pentane-1,5-diol(C) 1,2,3-hydroxy propane (D) Propane-1,2,3-triol

F-2. The IUPAC name of the compound is

3

23

CH|

NHCHCHCH|Ph

(A) 1-amino-1-phenyl-2-methyl propane (B) 2-methyl-1-phenyl propane-1-amine(C) 2-methyl-1-amino-1-phenyl propane (D) 1-isopropyl-1-phenyl methyl amine

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

(A) 1,1-dimethyl-3-hydroxy cyclohexane (B) 3,3-dimethyl-1-hydroxy cyclohexane(C) 3,3-dimethyl-1-cyclohexanol (D) 1,1-dimethyl-3-cyclohexanol

F-4. The IUPAC name of acetyl acetone is:(A) 2,5-Pentane dione (B) 2,4-Pentane dione (C) 2,4-Hexane dione (D) 2,4-butane dione

F-5. IUPAC name of is:

(A) 5-methyl hexanol (B) 2-methyl hexanol(C) 2-methyl hex-3-enol (D) 4-methyl pent-2-en-1-ol

F-6. The IUPAC name of

3

3223

CH|

CHCHNCHCH is:

(A) N-methyl-N-ethylethylamine (B) diethyl methylamine(C) N-ethyl-N-methyl ethanamine (D) methyl diethylamine

F-7. The IUPAC name of the compound:

(A) Propylene Oxide (B) 1,2-Oxo propane(C) 1,2-Epoxy propane (D) 1,2-Propoxide






VKP SirM.Sc. IT-BHU

F-8. The IUPAC name of is

(A) 3-Methyl cyclobut-1-en-2-ol (B) 4-Methyl cyclobut-2-en-1-ol(C) 4-Methyl cyclobut-1-en-3-ol (D) 2-Methyl cyclobut-3-en-1-ol

F-9. Ethyl methyl vinyl amine has the structure -

(A) CH CH N CH CH CH

CH

3 2 2 2

3

|

(B) CH CH N CH CH

CH

3 2 2

3

|

(C) CH CH N CH CH

CH

2 2

3

|

(D) CH N CH CH

CH

3 2

3

|

F-10. The IUPAC name of is -

(A) 4-oxopentan-2-ol (B) 4-hydroxypentan-2-one(C) pentane-4-ol-2-one (D) pentane-2-one-4-ol

F-11. All the following IUPAC names are correct except:(A) 1-chloro-1-ethoxy propane (B) 1-amino-1-ethoxypropane(C) 1-ethoxy-2-propanol (D) 1-ethoxy-1-propanamine

F-12. The IUPAC name of is -

(A) bicyclo [3.2.0] hexan-2-ol (B) spiro [3.2] hexan-1-ol(C) spiro [3.2] hexan-4-ol (D) spiro [2.3] hexan-4-ol

F-13. The IUPAC name of camphor is -

(A) 6-oxo-1,2,2- trimethyl bicyclo [2,2,1] heptane (B) 1,7,7-trimethyl bicyclo [2,2,1] heptan-2-one(C) 1,5,5-trimethyl bicyclo [2,1,1] hexan-2-one (D) 1,7,7-trimethyl bicyclo [2,1,2] heptan-2-one

Section (G) : IUPAC-Nomenclature of Functional groups

G-1. The correct IUPAC name of compound :

CNO|||

CHOCHCCHCH 23

(A) 2-cyano-3-oxopentanal (B) 2-formyl-3-oxopentanenitrile(C) 2-cyano-1,3-pentanedione (D) 1,3-dioxo-2-cyanopentane






VKP SirM.Sc. IT-BHU

G-2. The IUPAC name of compound

CHOCH||

CHCHCHCHCCH|||

CHO

3

33

3

is:

(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal(C) 2-Isopropyl-3-methyl-4-oxo pentanal (D) None of the above


ClNH||

HC—CCCH||CHOCHO

2

3

3

is:

(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid (B) 3-amino-4-chloro-2-methyl-2-pentenoic acid(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid (D) All of the above

G-4. The IUPAC name of the structure is:

COOHHOOC||

CHOCHCHNH2

(A) 3-amino-2-formyl butane-1, 4-dioic acid (B) 3-amino-2, 3-dicarboxy propanal(C) 2-amino-3-formyl butane-1, 4-dioic acid (D) 1-amino-2-formyl succinic acid

G-5. Which of the following compound is wrongly named?(A)

Cl|

CHCOOHCHCHCH 223 ; 2-Chloro pentanoic acid

(B)

3

3

CH|

CCHCOOHCCH ; 2-Methyl hex-3-enoic acid

(C) CH3CH2CH=CHCOCH3 ; Hex-3-en-2-one

(D)

3

223

CH|

CHOCHCHCHCH ; 4-Methyl pentanal

G-6. The IUPAC name of (C2H5)2

Cl|

COOH.CHNCH2 is:

(A) 2-chloro-4-N-ethylpentanoic acid (B) 2-chloro-3-(N,N-diethyl amino)-propanoic acid(C) 2-chloro-2-oxo diethylamine (D) 2-chloro-2-carboxy-N-ethyl ethane

G-7. The correct IUPAC name of

2

23

CH||

COOHCCHCH is:

(A) 2-methyl butanoic acid (B) 2-ethylprop-2-enoic acid(C) 2-carboxybut-1-ene (D) None of the above






VKP SirM.Sc. IT-BHU

G-8. IUPAC name will be

CNCNCN|||CHCHCH 22

(A) 1,2,3-Tricyano propane (B) Propane trinitrile-1,2,3(C) 1,2,3-cyano propane (D) Propane-1,2,3-tricarbonitrile


(A) 1,2,3-tricarboxy-2-propanol (B) 2-hydroxy propane-1,2,3 tricarboxylic acid(C) 3-hydroxy-3-Carboxy-1,5-pentane dioic acid (D) None

G-10. Which of the following is crotonic acid:(A) CH2= CH–COOH (B) C6H5–CH=CH–COOH

(C) CH3–CH=CH–COOH (D)

COOHCH||

COOHCH

G-11. The IUPAC name of

CH CHO

OHC CH CH CH CH CHO

2

2 2 2

|

is :

(A) 4, 4-di(formylmethyl) butanal (B) 2-(formylmethyl) butane-1, 4-dicarbaldehyde(C) hexane-3-acetal-1, 6-dial (D) 3-(formylmethyl) hexane-1, 6-dial

G-12. is named as :

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

Section (H) : IUPAC-Nomenclature of Functional groups

H-1. The IUPAC name of

2

3222

CONH|

CHCHCHCOCHBrCH is:

(A) 2-bromomethyl-3-oxo hexanamide (B) 1-bromo-2-amino-3-oxo hexane(C) 1-bromo-2-amino-n-propyl ketone (D) 3-bromo-2-propyl propanamide

H-2. One among the following is the correct IUPAC name of the compound

CHONCHCH|

H

23 (A) N-Formyl aminoethane (B) N-Ethyl formyl amine(C) N-Ethyl methanamide (D) Ethylamino methanal






VKP SirM.Sc. IT-BHU

H-3. The IUPAC name of compound

OHCH|

COOCHCHCOOCH

2

33

(A) methyl 2-hydroxymethylpropandioate (B) Methyl methyl-2-hydroxypropandioate(C) dimethyl-2-hydroxy methyl propandioate (D) 2-hydroxy methyl-dimethyl propandioate

H-4. The IUPAC name of is:

(A) 2-chlorocarbonyl ethylbenzoate (B) 2-carboxyethyl benzoyl chloride(C) ethyl 2-(chlorocarbonyl) benzoate (D) ethyl 1-(chlorocarbonyl) benzoate

H-5. Structural formula of isopropyl methanoate is:

(A)

3

33

CHO|||

CHCHOCCH (B)

(C)

3

223

CHO|||CHCHOCCH (D)

3

3

CHO|||

CHCHOCH

H-6. The IUPAC name of

OO||||

OHCCHOCCH 2 is:

(A) 1-acetoxy acetic acid (B) 2-acetoxy ethanoic acid(C) 2-ethanoyl oxyacetic acid (D) 2-ethanoyloxyethanoic acid

H-7. The correct systematic name of the above compound is:

O||

COOHCHCOCH 23

(A) 2-acetoxy ethanoic acid (B) 2-methoxy carbonyl ethanoic acid(C) 3-methoxy formyl ethanoic acid (D) 2-methoxy formyl acetic acid

H-8. The IUPAC name of the compound is :(A) Propanoic anhydride (B) Dipropanoic anhydride(C) Ethoxy propanoic acid (D) 1-Oxopropyl propanoate

H-9. The IUPAC name of the compound is :

(A) Cyclobutanedioic anhydride (B) Butanedicarboxylic anhydride

(C) Cyclobutanedicarboxylic anhydride (D) Butanedioic anhydride

H-10. Ethyl ethanoyloxyethanoate is :

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






VKP SirM.Sc. IT-BHU

H-11. 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

Section (I) : IUPAC-Nomenclature of Aromatic Compounds

I-1. The IUPAC name of is:

(A) 2-methoxy-4-nitro benzaldehyde (B) 4-nitro anisaldehyde(C) 3-methoxy-4-formyl nitro benzene (D) 2-formyl-4-nitro anisole

I-2. The IUPAC name of

56

3256

HC|

CClCHCHHC is ;

(A) 1,1,1-trichloro-3,3-diphenyl propane (B) 1,1-diphenyl-3,3,3-trichloro propane(C) both (A) and (B) (D) none of these

I-3. The IUPAC name of is -

(A) 1-amino-2-carboxybenzene (B) 2-amino-1-carboxybenzene(C) 1-amino-2-benzenecaroxylic acid (D) 2-aminobenzenecarboxylic acid

I-4. IUPAC name of

(A) 4-Chlorophenyl benzoate (B) Phenyl 4-chlorobenzenecarboxylate(C) Benzyl 4-chlorobenzenecarboxylate (D) 4-Chloro diphenylcarboxylate

I-5. 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

Section (J) : Structural Isomerism

J-1. Esters are fiunctional isomers of:(A) Hydroxy aldehyde (B) Ketone (C) Diketone (D) Diols

J-2. Which of the following is the first member of ester homologous series?(A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D) Ethyl methanoate






VKP SirM.Sc. IT-BHU

J-3. & are called as –

(A) Position isomers (B) Chain isomers(C) Function isomers (D) Ring chain isomers

J-4. Possible number of dichlorobenzene isomers is –(A) 1 (B) 2 (C) 3 (D) 4

J-5. Functional isomer of CH3COOCH3 is –(A) CH3CH2COOH (B) HOCH2—CH2CHO (C) Both of the above (D) None of the above

J-6. Propene and cyclopropane are –(A) Chain isomers (B) Position isomers (C) Geometrical isomers (D) None of the above

J-7. Metamerism is shown by -(A) Diethyl ether and n-propyl methyl ether (B) Ethyl alcohol and diethyl ether(C) Acetone and propionaldehyde (D) Propionic acid and acetic acid

J-8. Which of the following pairs of compounds are not metamers ?(A) CH3OCH2CH2CH3 and CH3CH2OCH2CH3(B) CH3CH2OCH2CH3 and CH3OCH(CH3)2(C) CH3NHCH2CH2CH3 and CH3CH2NHCH2CH3(D) CH3NHCH2CH2CH3 and CH3NHCH(CH3)2

J-9. Which compound is not the isomer of 3-Ethyl-2-methylpentane ?

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

J-10. What is the correct relationship between the following compounds ?

(A) Chain isomers (B) Position isomers (C) Functional isomers (D) Identical

J-11. Which one of the compound is not isomer of others ?

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

J-12. 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-13. Molecular formula C4H10O represent :(A) Two primary alcohol (B) One secondary alcohol(C) One tertiary alcohol (D) All of these

J-14. Aldehydes show with each other :(A) Chain isomers (B) Position isomers(C) Functional isomers (D) Both (A) and (B)






VKP SirM.Sc. IT-BHU

J-15. Which of the following is not an isomer of 1-butyne ?(A) but-2-yne (B) buta-1, 3-diene (C) but-2-ene (D) methyl cyclopropene

J-16.

COOH

& OCOH

functional isomer

EtOMe

& Me

OEt

metamers

CH – CH – OH2 2

&

CH – O – CH2 3

metamers

Me – N – Me

&

CH – NH – CH2 3

Functional isomers

(A) TFTF (B) FTTF (C) TTFT (D) TFFT

J-17. Which of the following is not the correct relationship

Me

OHMeMe

IO – Me

MeMe

II III

Me

OHIV

Me

O–Me

(A) II & IV are metamer (B) I & II are functional isomer(C) I & III are chain isomer (D) I and IV are positional isomer

J-18. Which of the following is not an isomer of compound CH3 – CH2CHO ?

(A) (B) (C) (D) CH2=CH–CH2–OH

Section (K) : Number of Structural Isomers

K-1. How many positional isoemrs are possible for dimethylcyclohexane :(A) 3 (B) 4 (C) 5 (D) 6

K-2. How many positional isoemrs are possible for 3-ethylpentane (including it self)(A) 1 (B) 2 (C) 3 (D) 4

K-3. The total number of unsaturated cyclic structure possible for a compound with the molecular formula C4H6is:(A) 3 (B) 4 (C) 5 (D) 6

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






VKP SirM.Sc. IT-BHU

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

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

K-7. The number of primary, secondary and tertiary amines possible with the molecular formula C3H9Nrespectively:(A) 1, 2, 2 (B) 1, 2, 1 (C) 2, 1, 1 (D) 3, 0, 1

PART - II : MISCELLANEOUS QUESTIONS

Comprehensions Type :Comprehension

The international group IUPAC has developed a detailed. system of nomenclature that we call the IUPAC

rule. Which are accepted throughout the world as the standard method for naming organic compounds. In

this system Alkyl groups are named by replacing the ‘-ane’ suffix of alkane name with ‘-yl’ like methyl ethyl

etc. complex alkyl groups are named. by a systematic method using the longest alkyl chain as the base

alkyl group. The base alkyl group is numbered beginning with the carbon atom bonded to the main chain.

The substitutes on the base alkyl group are listed with appropriate number and parentheses are used to

set off the name of the complex alkyl group.

1. Give the IUPAC name of following alkyl group

CH3 CH CH CH2

CH3

CH3

(A) (Di-isohexyl) (B) (2,3-dimethyl butyl) (C) (2,2-dimethyl butyl) (D) (2,-methyl-3-ethylbutyl)

2. Choose the correct IUPAC name of following alkyl group CH2 CH CH2

OH CH3

(A) (2-methyl-3-Propanoyl) (B) (3-hydroxy-2-methyl propyl)(C) (2-methyl-3-hydroxy propyl) (D) (1-hydroxy-2-methyl propyl

3. The structure of (2,2-dimethyl-3-ethylpentyl) group is -

(A)

CH3 C CH CH2 CH2

CH3

CH3

C2H5

(B)

CH3 CH C CH2 CH2

CH3

CH3

C2H5

(C)

CH3 CH2 CH C CH2

CH3

CH3

C2H5

(D) None of these

4. (2-propenyl) group is -

(A) CH2=CH–CH2– (B) CH3–CH=CH–

(C) Both (A) and (B) (D) None of these






VKP SirM.Sc. IT-BHU

Assertion / Reasoning TypeDIRECTIONS :

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; Statement-2 is a correct explanation for Statement-1.

(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.

(C) Statement-1 is True, Statement-2 is False.

(D) Statement-1 is False, Statement-2 is True.

(E) Statement-1 and Statement-2 both are False.

5. Statement-1 : H

CN is called cyclohexanenitrile.

Statement-2 : : It contains six carbon atoms in the ring and CN as the functional group.

6. Statement-1 : The locant (2,8,7) is preferred over the locant (3,4,9).

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.

7. Statement-1 : The IUPAC name of CH3CH=CH–CCH is pent-3-en-1-yne and not pent-2-en-4-yne.

Statement-2 : While deciding the locants for double bond and triple bonds. lowest locant rule for multiple

bonds is followed.

8. Statement-1 : The IUPAC name for the compound C2H5 C CH2OH

CH2

is -

2-ethylprop-2-en-1-ol.

Statement-2 : Ethyl (C2H5) rather than methylene (=CH2) is considered as the substituent group because

‘e’ of ethyl comes first in alphabetically order than ‘m’ of methylene.

9. Statement-1 : The IUPAC name for

O is 7-oxabicyclo [4. 1. 0] heptane.

Statement-2 : The prefix oxo is used for the C=O group.






VKP SirM.Sc. IT-BHU

PART - I : MIXED OBJECTIVE


1. The IUPAC name of

BrOH||

CHCCHCHCHCHCH|Br

32223 is

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

2. IUPAC name of 4-Isopropyl m-xylene is :(A) 1-Isopropyl 2, 4-dimethyl benzene (B) 4-Isopropyl-m-xylene(C) 1-Isopropyl-3, 5-dimethyl benzene (D) 4-Isopropyl-3, 5-dimethyl benzene

3. The structure of 2-(3-oxobutyl)cyclohexanone is :

(A) (B)

(C) (D)

4. The compounds with molecular formula C100H202 can show(A) Metamerism (B) Position and chain isomerism(C) Functional isomerism (D) Ring-chain isomerism

5. How many primary amines are possible for the formula C8H11N (only Aromatic structural isomers)(A) 4 (B) 6 (C) 7 (D) 14

6. The total number of aromatic isomeric ethers of molecular formula C8H10O is(A) Six (B) Seven (C) Four (D) Five

7. How many structural isomers could be obtained from molecular formula C2FCl BrI(A) Four (B) Five (C) Six (D) Three

8. Which type of isomerism is observed between I and II.

and

(A) Functional isomerism (B) Metamerism(C) Optical isomerism (D) Geometrical isomerism

9. Which of the following compound does not have molecular formula C6H6(A) Hexa-1, 3-dien-5-yne(B) 3-(2-cyclopropenyl)cycloprop-1-ene(or Bicyclopropenyl)(C) Cyclohexa-1, 3-diene-5-yne(D) Cyclohexa-1, 3, 5-triene






VKP SirM.Sc. IT-BHU

10. IUPAC name of is

(A) 3, 5-Dimethylcyclohex-1-ene (B) 4, 6-Dimethylcyclohex-1-ene(C) 1, 5-Dimethylcyclohex-2-ene (D) none of these

11. Which of the following are isomers

(A) I, II only (B) III, IV only (C) I, II, III (D) All

12. Total number of structurally different dichloropropanes is(A) 2 (B) 3 (C) 4 (D) 5

13.* Consider the following structures :

I

Cl–CH–CH–CH–CH 2223 CH – C – CH3 3

CH3

ClII

Cl

III

– CH – Cl2

IV

(A) I & II are chain isomers (B) I & III are functional isomers(C) II & IV are functional isomers (D) III & IV are chain isomers

PART - II : SUBJECTIVE QUESTIONS

Allot the IUPAC name to the following compounds :

1. 2. 3.

4. 5. 6.

7. 8. CH2=CH–

Br|C=CH–CH=CH2 9. 33

22

CHCCCCCH||||CHCH

10. 11. 12. CH2 = CH – CH2 – N C






VKP SirM.Sc. IT-BHU

13. 14. 15.

16. CH3OCH2OCH2CH2OCH3 17. 18. CH3 – CH2 – O – C(CH3)3

19. 20. 21.

H|

CHNCHCHOCH 3223

22.

23. Identify the molecular weight of the compound ‘X’ containing carbon and hydrogen atoms only with 3 and2 bonds in one molecule.

24. Find the hybridization state of each carbon atoms in following compound.CH2 = C = CH – CH2 – C C – CH2 – NH2

25. Calculate the molecular weight of the lowest hydrocarbon which contains sp & sp2 hybridised carbon atomsonly.

26. Which isomerism is shown by and

27. The ring chain functional isomer of compound But-2-ene are.

PART - I : IIT-JEE PROBLEMS (PREVIOUS YEARS)


1. Write IUPAC name of the following : [JEE-2002]

2. Which of the following represents the given mode of hybridisation, sp2 – sp2 – sp – sp, from left to right?[JEE-2003]

(A) H2C = CH – C CH (B) CH C – C – C CH

(C) H2C = C = C = CH2 (D)






VKP SirM.Sc. IT-BHU

3. Write IUPAC name of the following : [JEE-2004]

4. IUPAC name of ClC||O

HC 56 [JEE-2006]

(A) Benzoylchloride (B) Benzenecarbonylchloride(C ) Chlorophenyl ketone (D) phenylchloroketone

5. The number of structural isomers for C6H14 is : [JEE-2007](A) 3 (B) 4 (C) 5 (D) 6

6. What is the IUPAC name of the following compound? [JEE-2008]

(A) 4-bromo-3-cyanopheol (B) 2-bromo-5-hydroxbenzonitrile(C) 2-cyano-4-hydroxybromobenzene (D) 6-bromo-3-hydroxybenzonitrile

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

PART - II : AIEEE PROBLEMS (PREVIOUS YEARS)

1. Of the following compounds which has a wrong IUPAC name - [AIEEE-2002]

CH3 – CH2 – CH2 –

O|| C – O – CH2 – CH3

ethyl butanoate CH3 –

3CH| CH –

O|| C –

3CH| CH – CH3

2,4 dimethyl -3- pentanone

H3C –

OH| CH – CH

| CH3

– CH3

2-methyl -3- butanolIV CH3 – CH2 – CH2 – CHO

butanal(1) (2) (3) (4) IV

2. The general formula CnH2nO2 could be for open chain : [AIEEE-2003](1) diketones (2) carboxylic acids (3) diols (4) dialdhydes.






VKP SirM.Sc. IT-BHU

3. The IUPAC name of CH3COCH(CH3)2 is – [AIEEE-2003](1) 4-methylisopropyl ketone (2) 3-methyl-2-butanone(3) Isopropylmethyl ketone (4) 2-methyl-3-butanone

4. The IUPAC name of the compound [AIEEE-2004]

is -

(1) 3,3 -dimethyl-1-hydroxy cyclohexane (2) 1, 1 – dimethyl–3– hydroxy cyclohexane(3) 3,3-dimethyl-1-cyclohexanol (4) 1,1 - dimethyl - 3- cyclohexanol

5. Write IUPAC name of the following : [AIEEE-2005]

6. The IUPAC name of the compound shown below is - [AIEEE 2006]

(1) 6-bromo-2-chlorocyclohexene (2) 3-bromo-1-chlorocyclohexene(3) 1-bromo-3-chlorocylohexene (4) 2-bromo-6-chlorocycohex-1-ene

7. The IUPAC name of [AIEEE 2007]

is –

(1) 1, 1-diethyl-2-dimethylpentane (2) 4, 4-dimethyl-5, 5-diethylpentane(3) 5, 5-diethyl-4, 4-dimethylpentane (4) 3-ethyl-4, 4 dimethylheptane

8. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC

system of nomenclature is [AIEEE 2008]

(1) –SO3H, –COOH, –CONH2, –CHO (2) –CHO, –COOH, –SO3H, –CONH2

(3) –CONH2, –CHO, –SO3H, –COOH (4) –COOH, –SO3H, –CONH2, –CHO

9. The IUPAC name of the following compound is : [AIEEE-2009, 3/160]

(1) 4-Bromo-3-cyanophenol (2) 2-Bromo-5-hydroxybenzonitrile(3) 2-Cyano-4-hydroxybromobenzene (4) 6-Bromo-3-hydroxybenzonitrile

10. The IUPAC name of neopentane is : [AIEEE-2009](1) 2, 2-dimethylpropane (2) 2-methylpropane(3) 2, 2-dimethylbutane (4) 2-methylbutane






VKP SirM.Sc. IT-BHU

NCERT QUESTIONS

1. Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary,secondary , tertiary), vinyl or aryl halides :

(i) (CH3)2CHCH(Cl)CH3 (ii) CH3CH2CH(CH3)CH(C2H5)Cl

(iii) CH3CH2C(CH3)2CH2I (iv) (CH3)3CCH2CH(Br)C6H5

(v) CH3CH(CH3)CH(Br)CH3 (vi) CH3C(C2H5)2CH2Br

(vii) CH3C(Cl)(C2H5)CH2CH3 (viii) CH3CH=C(Cl)CH2CH(CH3)2

(ix) CH3CH=CHC(Br)(CH3)2 (x) p-CIC6H4CH2CH(CH3)2

(xi) m-CICH2C6H4CH2C(CH3)3 (xii) O-BR-C6H4CH(CH3)CH2CH3

2. Give the IUPAC names of the following compounds :(i) CH3CH(Cl)CH(Br)CH3 (ii) CHF2CBrClF

(iii) ClCH2C CCH2Br (iv) (CCl3)3CCl

(v) CH3C(p-ClC6H4)2CH(Br)CH3 (vi) (CH3)3CCH=ClC6H4I-p

3. Write IUPAC names of the following compounds :

(i) (ii) (iii)

(iv) (v) (vi)

(vii) (viii) (ix)

(x) C6H5–O–C2C2H5 (xi) C6H5–O–C7H15(n–) (xii)






VKP SirM.Sc. IT-BHU

4. Write structures of the compounds whose IUPAC names are as follows :(i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol(iii) 3, 5-Dimethylhexane-1, 3, 5-triol (iv) 2, 3-Diethylphenol(v) 1-Ethoxypropane (vi) 2-Ethoxy-3-methylpentane(vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol(ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol.

5. Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names.

6. Name of the following compounds according to IUPAC system of nomenclature :(i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl(iii) CH3CH=CHCHO (iv) CH3COCH2COCH3

(v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p

7. Draw the structures of the following compounds :(i) 3-Methylbutanal (ii) p-Nitropropiophenone(iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-ene-2-one(v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid(vii) p, p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid

8. Write the IUPAC names of the following ketones and aldehydes. Wherever possible, give also commonnames:(i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2(CH3)CHO(iii) CH3(CH2)5CHO (iv) Ph–CH=CH–CHO

(v) (vi) PhCOPh

9. Write IUPAC names of the following compounds and classify them into primary, secondary and tertiaryamines.(i) (CH3)2CHNH2 (ii) CH3(CH2)2NH2 (iii) CH3NHCH(CH3)2

(iv) (CH3)3CNH2 (v) C6H5NHCH3 (vi) (CH3CH2)2NCH3

(vii) m-BrC6H4NH2

10. Write structures of different chain isomers of alkanes corresponding to the molecular formula C6H14. Alsowrite their IUPAC names.

11. Write IUPAC names of the following compounds :(i) (CH3)3CCH2C(CH3)3 (ii) (CH3)2C(C2H5)2 (iii) tetra – tert – butylmethane






VKP SirM.Sc. IT-BHU


(i) (ii)

(iii) CH2=C(CH2CH2CH3)2 (iv)

13. Write structures and IUPAC names of different structural isomers of alkenes corresponding to C5H10.

14. Draw cis and trans isomers of the following compounds. Also write their IUPAC names :(i) CHCl=CHCl (ii) C2H5CCH3=CCH3C2H5

15. Write structures of different isomers corresponding to the 5th member of alkyne series. Also write IUPACnames of all the isomers. What type of isomerism is exhibited by different pairs of isomers ?


(a) CH3CH=C(CH3)2 (b) CH2=CH–C C–CH3 (c)

(d) (e) (f)

(g)

17. For the following compounds, write structural formulas and IUPAC names for all possible isomers havingthe number of double or triple bond as indicated :(a) C4H8 (one double bond) (b) C5H8 (one triple bond)






VKP SirM.Sc. IT-BHU

EXERCISE # 1PART # I

A-1. (D) A-2. (C) A-3. (C) A-4. (B) A-5. (B) A-6.* (ABD) A-7. (D)

A-8. (B) A-9. (D) A-10. (B) A-11. (B) A-12. (B) B-1. (D) B-2. (D)

B-3. (B) B-4. (A) B-5. (B) B-6. (A) B-7. (D) B-8. (D) B-9. (D)

C-1. (D) C-2. (C) C-3. (A) C-4. (C) C-5. (B) C-6. (B) C-7. (D)

C-8. (B) D-1. (C) D-2. (B) D-3. (A) D-4. (C) D-5. (B) D-6. (C)

D-7. (D) D-8. (A) D-9. (A) D-10. (A) D-11. (B) E-1. (D) E-2. (B)

E-3. (A) E-4. (A) E-5. (D) E-6. (C) E-7. (A) E-8. (B) E-9. (C)

E-10. (B) E-11. (A) E-12. (A) E-13. (B) F-1. (D) F-2. (B) F-3. (C)

F-4. (B) F-5. (D) F-6. (C) F-7. (C) F-8. (B) F-9. (B) F-10. (B)

F-11. (B) F-12. (D) F-13. (B) G-1. (B) G-2. (C) G-3. (B) G-4. (C)

G-5. (B) G-6. (B) G-7. (B) G-8. (D) G-9. (B) G-10. (C) G-11. (D)

G-12. (C) H-1. (A) H-2. (C) H-3. (A) H-4. (C) H-5. (D) H-6. (D)

H-7. (B) H-8. (A) H-9. (D) H-10. (D) H-11. (B) I-1. (A) I-2. (A)

I-3. (D) I-4. (B) I-5. (C) J-1. (A) J-2. (C) J-3. (A) J-4. (C)

J-5. (C) J-6. (D) J-7. (A) J-8. (D) J-9. (B) J-10. (A) J-11. (D)

J-12. (D) J-13. (D) J-14. (A) J-15. (C) J-16. (C) J-17. (D) J-18. (A)

K-1. (B) K-2. (A) K-3. (B) K-4. (B) K-5. (B) K-6. (D) K-7. (C)

PART # II

1. (B) 2. (B) 3. (C) 4. (A) 5. (D) 6. (A) 7. (A)

8. (C) 9. (B)


1. (A) 2. (A) 3. (B) 4. (B) 5. (D) 6. (D) 7. (D)

8. (B) 9. (C) 10. (A) 11. (C) 12. (C) 13.* (AD)

PART # II

1. 3-(1-Chloroethyl)-4-methyl-4-phenylpentan-2-one 2. 2-Cyclopropyl-4-ethylhex-1-ene3. 6-isopropylcyclodec-1-yne 4. 1-Chloro-2, 3-epoxypropane5. 3-Mercaptobenzoic acid 6. N, N-Diethyl cyclohexanecarboxamide7. 3–Cyclopropyl-3-methylbutanal 8. 3–Bromohexa–1, 3, 5–triene9. 2–Methyl–3–methylenehex–1–en–4–yne 10. 3–Methoxy–5, 5–dimethylcyclohex–2–en–1–ol11. 2–Bromo–1–chloro–3–iodocyclohexane 12. Carbylamineprop-2-ene13. 1, 1, 1–Trichloro-2, 2-bis(4–chlorophenyl)ethane 14. 1–(3–bromophenyl)–6–phenylhexa–1,3,5–triyne15. 3–Methyl–2–(3–oxobutyl)cyclohexan-1-one 16. 2, 4, 7-Trioxaoctane17. 1, 3, 5, 7-Tetraoxacyclooctane 18. 2-Ethoxy-2-methylpropane






VKP SirM.Sc. IT-BHU

19. N-Methylbenzamide 20. 3-Ethylphenyl ethanoate21. N-Methyl-2-methoxy-1-ethanamine 22. Pentano-5-lactone

23. H – C º C – H, Mol wt. = 26 24.

25. H2C = C = CH2 ;M.W. = 40. 26. Metamerism 27. ,


1. (4-Hydroxyphenyl) ethanal 2. (A) 3. 3-Aminobenzoic acid 4. (B)

5. (C) 6. (B) 7. 5

PART # II

1. (3) 2. (2) 3. (2) 4. (3) 5. 4-Methylbenzenesulphonic acid

6. (2) 7. (4) 8. (4) 9. (2) 10. (1)

EXERCISE # 4NCERT QUESTIONS

10. (i) CH3–CH2–CH2–CH2–CH2–CH3 n-Hexane (ii) CH3–

3

CH|CH

–CH2–CH2–CH3 2-Methylpentane

(iii) CH3–CH2–

3

CH|CH

–CH2–CH3 3-Methylpentane (iv) CH3–

3

CH|CH

–

3

CH|CH

–CH3 2, 3-Dimethylbutane

(v) CH3–

3

3

CH|C|CH

–CH2–CH3 2, 2-Dimethylbutane

11. (i) 2, 2, 4, 4-Tetramethylpentane (ii) 3, 3-Dimethylpentane (iii) 3, 3-Di-tert-butayl-2, 2, 4, 4-tetramethylpentane

12. (i) 2, 8-Dimethyl-3, 6-decadiene ; (ii) 1, 3, 5, 7 Octatetraene ;(iii) 2-n-Propylpent-1-ene ; (iv) 4-Ethyl-2, 6-dimethyl-dec-4-ene ;

13. (a) CH2=CH–CH2–CH2–CH3 Pent-1-ene (b) CH3–CH=CH–CH2–CH3 Pent-2-ene

(c) CH3–

3

C|CH

=CH–CH3 2-Methylbut-2-ene (d) CH3–

3

CH|CH

–CH=CH2 3-Methylbut-1-ene

(e) CH2=

3

C|CH

–CH2–CH3 2-Methylbut-1-ene

14. (i) (ii)

15. 5th member of alkyne has the molecular formula C6H10. The possible isomers are :

Documents

Contents · Contents Syllabus IUPAC Nomenclature & ... Rules for Naming the compound having poly functional groups : - If any organic compound possess more than one functional