Chapter

ORGANIC CHEM.- BASICS

I UPAC NAMI NG
COMPOUNDSCONTAI NI NG SI NGLE BONDS

1)

2)

3)

4)

5) 6)

7) 8)

9) 10)

11)

12)

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13) 14)

15) 16)

17)

18)

19)

20)

21)
COMPOUNDSCONTAI NI NG MULTI PLE BONDS

1)

2)

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3)

4) 5)

6) 7)

8) 9)

10)

COMPOUNDSWI TH FUNCTIONAL GPS.

1) 2)

3 4)

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5) 6)

7) 8)

9) 10)

11)

12)

13)

14)

15) 16)

17)

18)

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19) 20)

21)

22)

23) 24)

25) 26)

27) 28)

29)

30)

31)

32) 33)

34)

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35)

36)

37)

38)

40)
39)

41) 42)

43) 44) 45)

46)
DRAW STRUCTURES& BOND LI NE FORMULA
(1) 1, 1-Dibromo-3-ethyl- 4-flourohexane
(2) 5-Bromomethyl-6-methylhept-3-ene
(3) 2-Methylpentane-2,4-diol
(4) 4-Methylhexan-2-ol
(5) 3-Ethynylhexa-1,4-diene
(6) 2-Cyano-3-oxopentanedioic acid

(7) 3-Methyl-2-methylenebut-3-enoic acid

8) 3-Methoxycarbonylpropanoic acid
9) 3-Bromocyclohexane-1-sulphonic acid
10) 3-Cyano-3-ethoxy-4-nitropentanoyl bromide
(11) 5-Oxocyclohex-2-ene-1-carbonitrile
(12) 4-Formyl-2-oxocyclohexane-1-carboxylic acid.
(13) 3-Methoxy-5, 5-dimethylcyclohex-2-en-1-ol

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(14) 5–Methyl-2-(methylethyl) cyclohexan-1-amine
(15) 2–Chloro–3–methylcyclohex–3–ene–1–thiol

(16) 3 –Bromo– 4–methyl cyclopentan-1-one

(17) 2-Methylhept-3-ene
(18) 2,6-Dimethylhepta-1, 5-diene

I UPAC NAMI NG OF CYCLIC COMPOUNDS

1) 2) 3)

4) 5) 6)

7) 8)

9)

10)

11)

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12)

13) 14)

15) 16)

17) 18)

19) 20)

21)

22) 23) 24)

25)

26)

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27) 28)

29)
DRAW STRUCTURES& BOND LI NE FORMULA
(1) 1-Cyclobutylprop-1-ene
(2) 2-Methoxybutan-1-ol
(3) 3-Methylcyclohexene

(4) 1, 3-Dicyclopentyl propane

(5) 1-Methyl-4-propylcyclohexane
(6) 2-Ethyl-1,1-dimethylcyclopentane
7)5-sec-butyl, 4-isopropyldecane

8) 4-tert-butyl, 4-ethyl-2, 2, 5, 5-tetra methyl

hexane

I UPAC NAMI NG OF FUNCTIONAL GPS.&CYCLIC

1)

2)

3)

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4)

5)
I UPAC NAMI NG OFAROMATIC

1 2)

3) 4)

5) 6)

7) 8)

(9) (10)

(11) (12)

(13)

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 (14)

(15)

(16)

(17)

(18)

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 I somerism
Whentwo or more compoundshave same molecular formula but they differ intheir physical propertiesor chemical
propertiesor boththenthey are called isomers& the phenomena iscalled isomerism.
Classificationof isomerism

Structural isomerism:
Whentwo or more organic compoundshave same molecular formula but different structural formula

ChainI somerismor nuclear isomerismor skeletal isomerism

Chainisomershave the same molecular formula but differ inthe order inwhichcarbonatomsare bonded to eachother.
EG. Molecular formula isC5H12

CH3 – CH2 – CH2 – CH2 – CH3

Positionisomerism:
Whentwo or more organic compoundshave same molecular formula but they differ inthe positionof the functional group
or the substituent,
thenthey are called positionisomers& the phenomena iscalled positionisomerism.

Functional isomerism
Compound having same molecular formula but different functional groupsintheir moleculesshow functional isomerismand
are called functional isomers.

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Ring chainisomers:
Whentwo or more organic compoundshave same molecular formula but they differ intheir structuresdue to one being a
cyclic compound & the other one anopenchaincompound, thenthey are called ring chainisomers
EX. all isomersof C4H8

Metamerism
Thistype of isomerismisdue to the difference inthe nature of alkyl groupsattached to the polyvalent atomor functional
group.
Ex. C2H5 – O – C2H5C3H7 – O – CH3
Diethyl etherMethyl propyl ether
Tautomerism
Tautomerismisthe phenomenon inwhichtwo structural isomersdiffer inthe relative positionsof their atomsand are
spontaneously interconvertable and canexist indynamic equilibrium.
Two compoundshave different functional groupsdue to shiffting of H-atom.

e.g.

ClassificationofStereoisomers:

Configurational I somers
(I ) These isomersdiffer inthe configuration(The spatial arrangement of atomsthat characterisesa particular
stereoisomer iscalled itsconfiguration).
Geometrical isomerism:
I somerswhichpossessthe same molecular and structural formula but differ inthe arrangement of atomsor groupsin

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space due to restricted rotationare knownasgeometrical isomersand the phenomenonisknownasgeometrical
isomerism.
Conditionsof geometrical isomerism:
(I ) Geometrical isomerismarisesdue to the presence of a double bond or a ring structure.
Due to the rigidity of double bond or the ring structure the moleculesexist intwo or more orientations.

(I I ) Different groupsshould be attached at eachdoubly bonded atom.

, ,

Configurational nomenclature ingeometrical isomerism:

Config Criteria Remarks
If the two similar groupsare
cis/ Similarity of onsame side of restricted
trans groups bond the configurationiscis
otherwise trans.
If the two senior groupsare
onsame side of restricted
Seniority of bond the configurationisZ
E/Z groups (Z=zusammen=together)
otherwise E (E =entgegen=
opposite).

For deciding the seniority of groupsfollowing rulesare applied :

Rule I : The group withthe first atomhaving higher atomic number issenior.
Rule I I : The higher massisotope issenior.
Rule I I I : If the first atomof group isidentical thensecond atomisobserved for seniority.
Rule I V: Groupscontaining double or triple bondsare assigned seniority

Physical Propertiesof Geometrical I somers:

Conformational I somerism

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Different arrangementsof atomsthat canbe converted into one another by rotationabout single bondsare called
conformations.

Projections:

To write newmanprojectionformula. The front carbonand itsother bondsare represented as and those of the back

carbonas
Dihedral angle : The angle betweenC – X and C – Y inX – C – C – Y whenit isvisualised along C – C bond.

Staggered, eclipsed and skewconformations:

(I ) The staggered conformationof a molecule isthat conformationwhere the dihedral angle betweenthe bondsat each
atomof carbon-carbonbond is60°, 180°,300°.
(I I ) I ntheneclipsed conformationthe atomsbonded to carbonsat eachend of carbon-carbonbond are directly
opposite to one another. The dihedral angle betweenthemis0°, 120°, 240°.

(I I I ) Skew conformation: All conformationsother thanstaggered or eclipsed are skew conformations.

Torsional strain: Any pair of tetrahedral carbonsattached to eachother tend to have their bondsstaggered for minimum
repulsionbetweentheir bonds. Any deviationfromthe staggered conformationare accompanied by torsional strain.
Conformational analysisof ethane :
The potential energy of ethane molecule isat a minimumfor the staggered conformation, increase withrotationand
reachesa maximumat the eclipsed conformation. Most ethane moleculesnaturally exist inthe most stable staggered
conformation.There are only three energy minima, that isethane hasonly three conformers.

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Stability order : Staggered >Ecilpsed

D.PLEVEL -1
1) The I UPAC name of CH3C CCH(CH3)2 is–
(A) 4-methylpent -2- yne
(B) 4,4 -dimethylpent -2- yne
(C) methyl isopropyl acetylene (D) 2-methylpent - 4 – yne

2) I UPAC name of is

(A) 2-Cyano-3-methylhexane
(B) 2,4, 4-trimethylpentanenitrile

(C) 2,2-Dimethyl-4-cyanopentane (D) 2-Cyano-3-methylhexane

3) The I UPAC name of is

(A) 1,1-dimethyl-1, 3-butanediol
(B) 4-methyl-2,4-pentanediol
(C) 2-methyl-2,4-pentanediol
(D) 1,3,3-trimethyl-1,3-propanediol

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4)

5)

6) 8)

9) 10)

11)

12)

13)

14)

15) 16)

17)

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18) HC C CH=CH CH2 C CH

19)
Draw the structuresof the following compounds
20) 2, 3 - Dimethyl-6- (2-methyl ethyl) decane
21) 5 – (1, 1-Dimethyl ethyl) – 6– ethyl–2– methyloctane
22) 1, 3 – Dichloro 2, 2–bis(2–chloroethyl) propane
23) 3 – isopropyl – 2, 4, 4 – trimethyl pentane
24) 3, 3, 6 – Trimethyl – 1, 4 – heptadiene

D.PLEVEL -2

1)The I UPAC name for

is

(A) 1,1-dimethyl-1, 3-butanediol (B) 4-methylpentane-2,4-diol

(C) 2-methyl-2,4-pentanediol (D) 1,3,3-trimethylpropane-1,3-diol
2) The I UPAC name of CH3COCH(CH3)2 is
(A) isopropylmethyl ketone
(B) 2-methyl-3-butanone
(C) 4-methylisopropyl ketone (D) 3-methyl-2-butanone

3) 4)

5)

6)

7)

8)

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9)
Draw the structuresof the following compounds
10) N – Ethyl – N – methylpropan– 2 – amine
11) 2 – methoxy – 2 – methylpropane

D.PLEVEL -3
1.Write the I UPAC namesof the following compounds:

(i)HOH2C –CH=CH– CH2OH(ii)

(iii) (iv)CH3COCOOH

(v) (vi)

(vii) (viii)

(ix) (x)

(xii) (xiii) [(CH3)2CH]3COH

(xiv)(CH3)3COH(xv)

(xvi)CH3CH2CH(CHO)CH2COOH(xvii)

2.Write correct I UPAC namesof the following polyfunctional compounds:

(i) CH2 =CH–CH2Cl(ii) CH3CHCHCH2OH

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(iii) (iv)

(v) (vi)

(vii) (viii)

(ix) (x) CH3CH2CHCH2CN

3.Write I UPAC namesof the following compounds:

(i) CH3OCH2CH2CH2OC2H5(ii)

(iii) (iv) HC=C–CH=CH–CH3

(v)

D.PLEVEL -4

1.(i)

(ii)

(iii)

(iv)

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(v)

(vi) (vii)

(viii)

(ix)
(x)

(xi)

(xii)
(xiii)
(xiv)
2.Give I UPAC name of the following compounds

(i)

(ii)

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(iii)

(iv)

(v)

(vi)
(vii)

(viii)

(ix)

(x)

D.P.SLEVEL -5

1) The correct name for the compound

(A) 2-bromo-5-hydroxyhexan-1-al
(B) 1-bromohydroxypentan-4-al
(C) 2-hydroxy-5-bromohexan-6-al (D) none of the above

2)

3)

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4)

5)
6)

7)

8) 9)

10)

11)

12)

13)

14)

15)

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16)
Draw the structuresof the following compounds
17) N, N – dimethyl ethanamide
18) 2-Butyl-4-chloro-5-methyl-2, 4-hexadienoylchloride
19) 3-Formyl pentanoic acid

D.P.SLEVEL-6

1) 2)

3) 4)

5) 6)

7) 8) 9)

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10) 11)

12)

13)

14)

15)

16)

17)

18)

19) 2 – (1– Cyclobutenyl) – 1– hexene

20) 1, 3 – Cyclohexadiene
21) 3 – Bromo – 2 – methyl cyclopent – 1– ene
22) 1, 1-dimethyl -2- isopropenyl cyclopentane

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