1.

IUPAC Nomenclature
DPP-1 Alkane, Cycloalkane and Halogenated Alkanes-l
1.
5. (d)
) CH,CH-CH, (1)

Br
4-ethyl-2-methyl-1-propyl cyclohexane

(on)
()
Br

Wrongly
1.3.4
nurnbered
(vi)
1.2.5

that molecular formula of

(vii) 6. (c) Molar mass 100 indicates
() hydrocarbon is C,H,e A quaternary carbon is
a carbon which is
but no hydrogen atom
bonded to four other carbon atoms
Hence,
CHg
Br CH3
'CH CH, 5
(0)
2, 2-dimethyl pentane
C|
ring as wellasa four carbon chain
7. (c) Here, we have a four carbon
B
directly on the ring. However, there are more locants present on
is the parent and ring is locant.
Br -CH3 open chain than on ring, chain
(Xi (xi) CHa
CH3

2-cyclobutyl-2-methyl butane
(x)
shown as:
8. (d) The correct numbering is
2. 0 3-10do-2. 5-dimethyl hexane
9-trimethyl-5-propyl decane
() 2-chloro-5-fluoro-3,3,
(n) 3-bromo-1, 1-dimethyl cyclohexane
(v) 5,6-dibromo-2, 2-dimethyl heptane 1, 2-diethyl-1, 8-dimethyl-5-propyl
cyclooctane
(V) 6-ethyl-2, 5.6-trimethyl octane from
1, 2, 3, 4, 5, 6 is obtained starting
(v) 5-propyl nonane 9. (b) Same number series Hence, numbering is done giVing
any carbon of the ring. group in
(vi) 2, 5-dimethyl-3-propyl heptane which comes before methyl
(Vil) 4-(-1-bromoethy)-5-(1-chloroethyl) octane preference to the ethyl group
alphabetical order.
(0) 3-bromo-5-chloro-2,7-dimethyl-4-(3-methylbutyl) octane
CH3
carbons. CH,CHe CH,CH3
(C) The longest chain has seven
6.
CH,CH CH3
CH3
1,2,4-triethyl-3,5,6-trimethylcyclohexane
3-ethyl-2, 5-d1methyl heptane
C-2.
appears at starts from bridge-head
first alkyl locant
In the correctt numbering shown, numbering other 10. (b) In bicyclic
compunds, numbering
is started from
while it would appear at C-3 if carbon.
Terminals of the parent chain. irrespective of 8
alphabetical
order
Locants name are writtenin although the former
written before methyl position C-2
positions-ethyl is lower
ll | locant is at
locant is s at C-3 while first methyl in
alphabetica

are considered
Also, original name of locants
order not d of prefix di. 4
8-methyl bicyclo [3, 2, 1] octane
4. (b) smaller ring
cycle is completed via larger ring to
Numbering
bridging carbon.
8 ending at
3-6-diisopropyl-2,6-dimethyl nonane
247
TIONS
EXPLANA

WITH
ANSWERS
 are available for Cl and
.
11. (a) positions
16. (c) Five different
CI
(a) Here, cyclopentane is the parent chain and cyclobulane lo
locant over locant methl. had not the cyclobutyl ring been () CH,-CH,-CH-Br Gi) CHg-C-CH,
directly on methyl locant, it would have been numbered
separately as in case of (b), (c)and (d) B
B
CH¡
(b () CHgCH-CH,0
(i) CH, H-CH,-Br

1-cyclobutyl-1-methyl 1-melhyl cyclobutyl () Br-CH,-CH,CH,-CI

cyclopentane cyclopentane
formula C,Han hence it could be.
CHa 17. (b) It is based ongeneral
alkene or a cycloalkane.
Since, it has no double ebond,
(d)
cycloalkane. It has one CH, group as trmustbe
CH3
1-cyclobutyl-2 (0) and (9)CH-CH
methyl cyclopentane
between two
12. (a) Cyclopentyl ring with three locants in the parent 1, 2, 4 is the 18. (d) If only one carbon is common ring
correct number series. Number 4is equidistant from both 1and 2. comes in spirene family. corngoung
Numbers 1 and2 are assigned in alphabetical order. The name here has prefix spiro followed by number of caroors r
carbon)
13. (c) Here the lowest numbered series is 1,1, 2, 5. No special the two rings (excluding common
preference is given to halide locants. Locants are written in
alphabetical order.
Br

Numbering start from smaller ring. Hence, name iS spiro [3 4

Octane.
C
19. (c) Here, only two chloro can be present on parent cha.
CH, remaining two would became further of methyl branches
5-bromo-1,1-dichloro-2-methyl cyclohexane
CHzCI
14. (d) 2-ethyl butane is a wrong name according to IUPAC CI
Convention as it has a five carbon continuous chain as
CH,CI
1, 3-dichloro-2, 2-bis(chloromethy) propane

20. (c) Compound is a trichloro derivative of propane. The thrs

It is 3-methyi pentane rather than 2-ethyl butane. chlorine atoms can have the following different positions.
15. (d) Open chain and cyclic ring, both have three carbon atoms in C
continuous chain but the open chain (propy) has three locants () CH CH,-CCI (0) CI-CH,-CH-CH,-C
while the ring has only two locants.

(i) CH,H-H-CI (v) CI--CH,-CH,CH-CI

C

Only two locants Three locants

() CH-C-CH,CI
C

DPP-2 Alkane, Cycloalkane and Halogenated Alkanes- ||

1. (c) Central ring has maximum of three locants, hence it is the
2. (d) The largest chain with maximum number of locants becoieo
parent ring. The lowest number series is 1, 2 and 4 as
the parent chain.
C

Br

Parent ring
4-(4-bromocyclohexyl)-1-(3-chlorocyclohexyl)-2-flucrocyclohexane
There is locant in the side rings, hence secondary numbering of 3,4,4-triethy-2,2,5-trimethyl
side rings are also done. hexane

DPP - GENERAL ORGANIC

248 CHEMISTRY AND HYDROCARBONS
 formed via
option (b) parent chain is wrongly nunmbered The corect 10. (a) There is only one C C bond which can be
3. (b) In
numbering is hydrogenation as
B
H,
CI
3.3. 4, 4 tetrarnothyl hezane
3-bromo-1-chlorobutane No any other positions are available for double bond due to
quaternary carbon atorns at C-3 and C-4
A) Central ring is the parent nane and numbering starts from
where two cyclopropyl locants are present
carbon

smutaneously
11. (c) Parent chain has nine carbon atorns.
rMolar nmass 84 IS a multiple of 14 hence, X is based on general
rmula C.H,,with molar mass 14n. Here, n is 6 and Xis CeH2
As Xhas no double bond, it must be a cycloalkane Cycloalkanes
without methyl as locant are

Oyclohexane Ethyl cyclobutane Branching in branch

Branch name 1,2-dimethyl propyl is treated as single alkyl locant

hence, its d is considered in alphabetical order.
Propyl Isopropyl C
cyclopropane cyclopropane 12. (d) C
6.(D Here the parent ring is wrongly numbered. (0) ()
B

CI (iv CI
(v) (vi)

C
(vi) C (vii)
2-bromo-1, 1-dichlorocyclobutane
Correct number series:1, 1,2
Wrong number series: 1,2, 2 Allthese (i)-(vii) have different IUPAC names.
(iower number coming at first occasion of difference is the correct 13. (c) It has only two different types of H-atom.
number series)

7. (c) Since, the compound is based on general formula CHan-2

CH, CHe,
and it has no double bond or triple bond, it must be a bicyclic
compound or a spiro compound. Gtg éHCH,
CH3

-CH3 H,
Here, four isopropyl groups bonded to *C are all equivalent
hence, only two different types of H-atom.
Bicyclo
14. (d) Given condition indicates that X has all the carbon atoms
either quaternary or a to quaternary carbon so that p1 (r) bonds
cannot be formed with them.
Spiro
CH3 CH,
3. (a) Its al hydrogens are equvalent, hence substitution of any of
the 18 hydrogens would yield the sarne, CH,- H, -CH,
1-bromo-2, 2.3.3-tetramethyl butane CHa CH,
CH, CH, 2, 2, 4, 4-tetramethyl pentane
CH,CH,
In this compound, C =C cannot be fornmed.
CH,Cc-CH, CH,C-CCH, Br
15. (b) Primary alkylgroup means the carbon to be bonded to parent
CH, CH, CH,CH, chain must be essentially CH, Hence,
CH2 CHy
(0) ()
(9) Since, only one alkene gives Xon hydrogenation, there is only
possible place for double bond in X.
CH3
CHm
H2
() (v) CH -CH, ~

CHa

ANSWERS WITH EXPLANATIONS 249

 16. (b, c) In option (a),the longest alkyl chain has not C
parent chain Both (b) and (c) satisfy the given been considered as
condition. CI C
(i (i)
(b) C
C
C

3-ethyl-2,2,4-trimethyl pentane (iu C (Iv)

C CI
CI
6 C
(c)

CI
2.2,3,4-tetramethyl hexane (V) (V) CI
In (d), there is no quaternary carbon
atom. C
17. (a, b, c) Option (d) is wrongly named as it
has a longer butyl chain as 19. (a, b, d) The correct name is
parent Others satisfy the condition
4-bromo-1, 1-dichlorocyclohexane.
18. (b, c) Option (a) is wrong because only
and 2-chloropropane can be assigned.
two different names, 1-chloro Br
Option (b) is correct as
CI

() CI CI
1,2-dichloropropane (i) 2, 2-dichloropropane
C 4-bromo-1,1-dichlorocyclohexane
20. (a, b, c) C,Hg is based on general formula
C C,H¡n-2 With two
CI degree of unsaturation. Unsaturation
arises due to
(i
1,2-d1chloropropane (iv) presence of pi() bonds or ring structure. Therefore, it the
1,3-dichloropropane an can be
Option (c) is correct as alkyne, a diene or a bicyclo alkane.
CI
C
CH-C=CCH3 A CH,=CH-CH=CH,
B
C
(u). (n)

CI
C,Hn-2 is also general formula of spirene
(iv) ) CI C spirene contain atleast 5 carbon but the smallest
spirene. atoms, hence it cannot be a

All the above five (i)- (v) have

different IUPAC names.
Option(d) is wrong as only six different names can be
assigned.
Smallest spirene, CsHg

DPP-3 Alkenes
1. (0) 2-methylbut-2-ene
(1) 5-cyciopropyl-2-rnethylhept-3-ene
(1) 6-ethyl-5,6-d1fluoro-3-methyloct-2-ene
(vi)
(iv) 4-chloro-5-ethyi cyclohexene (vii) (ix)
(v) 3-brorno-2-chlorohept-3-ene CHs
C
(vi) 3-chloro-5-10dohex-2-ene
(vi) 4-bromo-6, 6-dichlorohex-2-ene
(Xi)
(vIi) 6,6-dibrono-1-chlorocyclohexene
(ix) 3-(2,3-d1rnethylcyclopropyl) cyclopropene
() 3-cyclopropyl ethene
(xi) 3-chloro-2-(1-chloroethyl) pent-1-erne 3. (0)
4-butyl-3-ethyl-1,
4-hexadiene4-pentadiene
2. (i) 2-(2-chloroethyl)-4-methyl-1,
(i) (i) 2, 6-dimethyl-1, 3-cyclohexadiene
(iv) 6-bromo-5-chloro-6-methyl-2, 4-heptadiene
(v) 3,
C
6-d1methyl-1,
4-cycloctadiene
(v) 3-(4-cyclopropylcyclohexyl) cyclopropene
(v) (v) (vi) (vi) 2, 5-dicyclohexyl-1,3-cyclohexadiene
(vili) 3-(4-cyclobutyl) cyclobutene

250 DPP - GENERAL ORGANIC

CHEMISTRY AND
HYDROCARBONS
 1and
dichlotoethono lwo otforont positions,
ToWOv0, In tho two chlonne atornS
1, positions ae avalablo fo
4. CI
CHHCH C
()
CH,CCI, |2dichloroothone

I dichlooethene
(

13, (c)H,CCCH, Propadierno

C

()
THore, tho second carbon is sp hybrid1sed
numbering shown
(m)
14. (b) According lo the corect
Bi C

CI CH
(V)

CI
H
2.3,3-trichloro-1-propene

sc) Here double bond has pieleronce over halogen locants 15. (d) When numbering diene
preference is given to double bands
Hence. the corectnumbering is irrespective of positions of other alkyl and hal1de locants Hence
CI Correct numbering is
B
B

C,oHon:
6. b) Snce X has 8H (4H,) less than saturated alkane
B
However, it
Theretore, X has a total of 4 degree of unsaturation. 6 positions, had the compound
Here, halogen locants are at 5, 5,
which accournts for one degree of halogen locants would have came at 5.
has a cvcloalkyl group been numbered clockwise,
unsaturation is due to
unsaturation, remaining three degree of 6.6 which is wrong.
presence ol three double
bonds
than cyclohexyl ring. it is
whose molar 16. (c) Although, cyclobutenyl ring is smaller
double bond
7. (b) The general formula of alkene is ,H, or (Crt,),, X is
the parent ring due to preference to
70, n = 5 and
mass would be 14n. Hence, lor molar mass
CH, Various structures of X could be

Only ().(I) and (V) have 'ene' at 1-position. CI

giving lowest number to 3-(3,4,4-trichlorocyclohexyl) cyclobutene
8. (d) Parent chain must be numbered
double bond as way in which two double
17. (d) In cyclobutyl ring. there is only one
bonds can be present simultaneously, hence need not be
numbered.

B
5-bromo-2-chloro-4-methyl-2-hexene

Cyclobutadiene
that gives preference to double
3. (C) The correct nurnbering is one IUPAC
bond 18. (d) The be. hown five compounds will have d1fferent
CI
names

C
B V C
5-bromo- 1-chlorocyclohexene

brought on one sngle

TO. (c) Here, C-3 Is a quaternary Carbon atom 19. (ch) Here, all the double bonds cannot be
Dumber of double
chain Hence, the longost chan with maxmum
CH becomes the pafent chain
bonds

CH,
3,3-dimethyl-1-butene

possible
covalent bonds which is not
(0) Hero, C-3 Is hav1ng five
2 plopenyl loc ant Gpropeny) 1/docaahene
paent ong
20. (b) The ceotral ing willh tw0 dOUble bonds is the
1

equIvalont
unsubstituled ethene, both carbons are
e) In an locants, there is only one
Hence, for 1, 3 and sImilar halogen
Way in which they can be present CI CI
H CI
CI, CI C C I 3Dus(3-cyclupenteny) cycotutad ene
CH,=CIH-CI, CIC=C loltachloroelhene
Trichlor oothene
Chloroothene
ANSWERS WITH EXPLANATIONS
251
 DPP-4 Alkynes
1. (0) 2-tertiarybutyl-3-hexyne
8. (a) Paront chain is wrongly nurnbered. Triple bond is
(1) 4-ethyl-2-hexyne preferenco over alkyl and haltde locants Its Correct narne ic qver
(u) 2-chloro-6-cyclopropyl- 4-octyne Br
6
(iv) 2. 3,
(v)
3-tribromo-8-methyl-6-propyl-4-decyne
4. 6. 6-trichlorocyclooctyne 3 5

(vi) 3-chlorocyclohexyl ethyne Br

(vn) 3-1sopropyl-4-propyl-1,5-hexadiyne 5.5-dibrorno-1-hexyne
(vin) 5-(2-bromo-1-chloroethy)-2-octyne 9. (c) The general formula of alkyne is
(iX) 2. 2-dibromo-3-chloro-4, 7-0ctadiyne
C,Hn2 with molar mass 14n-2.
(x) 1-(1-chlorocyclopropy)-2-(2-chlorocyclopropyl) ethyne
’ 14n -2 = 96 ’n=7;C,Hp
2.
Possible internal alkynes can be found as:
()
() CH,-CH,--CH-CH,-C=CCH,
CH,
(1) CH4CH, H-C=0-CH,
(iv)

CH,
CH3 (ii) CH,-H-CH¡-C=C-CH,
(vi) (i) CHg-CH,-CH,C=C-CH,CH,
CH3 CH,
CH; CHs (v) CH¡(-C=C-CH,
() CHCC=C- -CH, (vii) CH,
CH, CH, CH3
(vi) CH4CH-C=C-CH,CH¡
Br Br
10. (d) Both (a) and (c) satisfy the condition.
() CH3 CH,
2H2
C
CH3 -CH,
CH, CH,
3. (c) Triple bond has preference over alkyl and halide locants. (a)
Hence. they are given lower number. CH, CH,
4. (b)
ÇHa
CHs -CH, CH-¢-CH,
C=0H CH, CH,
C=C-H 6 CHzand2 CH, groups
1-pentyne 3-nethyl-1-butyne
CH, CH,
2H>
5. (d) ln 2-hexyne, C-2 and C-3 are sp-hybridised. Therefore,
CCC bond angles of both 1,2,3 and2,3, 4carbons are 180°,
hence. C-1.C-2, C-3 and C-4 carbons lie on astraight line. CH, CH,
(c)
180 CH,CH,
3
1
CH--ç-CH,CH,-CH,
180°
CH, CH,
6. (c) According to given narne, the structural forrmula is 6 CH,and 2 CH, groups
Both above have 6 CH, and 2CH,
CHs groups.
11. (c) Parent chain is the alkyl chain
that
Cyclohexyl ring with chloro locant on it contain both triple borlu
chain. Since, there is locant on locant. theare locants on the pae
Here, C-2 has five covalent bonds which is not possible. are also numbered as: locants on parent Cria
7. (d) CoH,o is based on general forrnula C,H¡n-2, hence itcan be
an alkyne. Therefore, all(a), (b),(c), are possible name for the C=CH
3
given compound. Compound (d) has a cyclic ring and a triple
bond, giving three (1 for ring, 2 for triple bond) degree of
unsaturation which does not satisty the compound CgHo which
has only two degree of unsaturation.

DDP - GENERAL ORGANTC CHEMISTRY

252 AND HYDR0CARBoNS
12. (a)
18. (b)
CH,-H

5 6 6-tnmethyl-3-heptyne (i)

42 (c) Molecular formula corresponding to 2-butyne is CHe. Hence. CH,H

aresponding cycloalkenes may have a four or a three carbon Carbon 1,2 and 3 are colinear as
nngs as sp

180
4C rings 3Crings Also, it has only three (underlined) non-equvalent rydroger
gives three chloro alkynes in substitution reaction
14. (c) The given formula of Xindicates that it has two triple bonds (four (0) ’ (p,s)
degree of unsaturation). Hence, possible diynes are (i) CH-C=(-CH3
Sp Sp

180° 180
(iv All four carbons are colinear
Also, it has all six hydrogen equivalent, hence only one
(V product after a hydrogen is substituted by chlorine
(i) ’ (q.r)
All of the above five diynes have different IUPAC names. (ii) CH3-CH-C=C H
15. (b) Longest chain has eight carbon and locants as well as triple SD
sp
bonds are equidistant from the terminals. Hence, numbering is
done in alphabetical order giving preference to f1rst different 109° 180
locant cyclobutyl over cyclohexyl. Only three carbons col1near
Also, it has three non-equivalent (underlined) hydrogens
hence gives three different products after substitution of a H
by Cl
Br (ii) ’ (p,s)
CH,
16. (d) The longest chain including triple bond becomes the parent
chain Hence, here we have 8 carbon parent chain as.
(w) CH-¢-C=C-¢-CH,
H, CH,
Here, the two sp -hybridised carbons and twO -carbon
bonded to sp carbons are colinear
Also, all its hydrogen atoms are equvalent. gives
only one
chlorinated product on substitution of a Hby CI
ASO, it has a branched locant whose name would be (iv) ’ (g,)
-chloro-1,2-dirnethylpropyl and it is present at C-4 of the parent 19. (8) CH,-CH, CH-C=C-CH,-CH,-CH,
chain
3-ethyl-4octyne
(G) Molecular forrmula of alkyne is CHo, Various possible terminal
CH,-CH,
alkynes are All the hydrogens of- CH, are secondary, hence 8
secondary H
CH,
20. (4)
9 CH,- -C=CH
0) CHCC-H
CH,
CH,
) CH,-CH,-CH-C=CH CECH
CH;
(u)
) CH,-CH-CH,C=CH
C=C-H
All the above four terminal alkynes ()-(iv) have different IUPAC (V) c=c-H
narmes.
CH3

ANSWERS WITH EXPLANATIONS 253

 DPP-5 Aromatic Hydrocarbons
chlorinatio.
1. (0) 3-chlorotoluene or m-chlorotoluene 6. (b) It has only two non-equivalent positions for
(i) 3,5-disopropyltoluene C!
(i) 2-bromo-4-chloro- 1-(1-methyl propyl) benzene CH CH;CI
(Iv) 4-phenylhept-2-en-5-yne or 4-phenyl-2-hepten-5-yne
+
(v) 1-bromo-3-chloro-5-fluoro benzene
(vi) 3-phenyl toluene HC (b) H,C H,C
(vI) 1,2-dimethyl propyl benzene
Oniy two monochlorination products
(vi) 1-(2-bromopropyl)-3-chlorobenzene
(ix) Diphenyl ethyne CH,
CH-CH2
2
H
CH3

( H H

C CH3 H H
(a) (c) (d
3 non-equIvalent H 5 non-equivalent H 4 non-equivalent H

(IV) The number of monochlorination products in each case wouldhe

(v) equal to the number of non-equivalent H.

7. (b) Al the carbon of ring has halide B

locants hence, same number series
would be obtained in all cases. Therefore,
numbering would be done giving
(vii) preference to bromo locants as it comes
before chloro in alphabetical order. Br C
Ph Lowest possible numbers are given to
bromo lOcant positions. Br

(ix 8. (c) Following six compounds have different IUPAC names

(x)
C C
Ph Ph
CI
(Ph=Phenyl (CsHs)]
(0) (ii
S3. (d) Numbering starts from bromine's carbon as Br
C
CI B
Br
C C

Br B
(iv) (V (vi)
This is the lowest nunber given to locants (1,2, 4, 5) as well as
follow alphabetical order.
4. (d) C,H., hasa phenyl ring plus two carbon atoms which may be 9. (d) The correct numbering will have
present as an ethyl or two methyl locants as :
locants at 1, 2. and *
positions as:
Br
(a) (b) CHs

(C) (d)
2-bromo-4-chlorotoluene
10. (b) The correct numbering
Option (d) is infact 1,3-dimethyl benzene. of benzene ring is
B
5. (d) The correct numbering is

Also, cyclobutyl comes before

Br hence, the correct IUPAC name cyclopropyl in alphabetical ol
is
Here. branch is also numbered separately 2-bromo-4-cyclobutyl -1-cyclopropyl benzene.

DDP - GENERAL ORGANIC CHEMISTRY AND

254 HYDROCA RBON
 Resultant dipole moment of lis greater than that ofII. Since, l, +J= -2l + la
11. )
C not

3
C
12. 1
120°
Here,
Lnet =(u, t H3) = es
CI 120 C Thus,

18. (5)
=0 -CH2-CH3
b) AIl the lOcants are equidistant, numbering is done in
CI
13.
alphabetical order.
-CH-CHZCI -H-CH3
CH3

Ethenyl C
C
possible for dimethyl
14. (a) There are only three positional isomers Five monochlorination products
benzene.
CH3 CH3
CH3 1,2. 4 as
CH3 19. (7) The correct numbering gives the number series
CI B
2

CH3
C
CH3 6
2-bromo-1,4-dichloro benzene
1,4-dimethyl benzene
12-dirnethyi benzene 1.3-d1methyl benzene
dichloronaphthalene are
for dimethyl benzene. 20. (7) The total positional isomers of
Hence, the IUPAC names pOssible the labelled Polar dichloronaphthalenes
C
15. (b) In iso-propyl benzene, CsHs-CHCH C

CH,
carbon is only tertiary carbon.
aiven trichlorobenzene is due to
character of CI CI
TO. (b) The non-polar
individual dipole mornents by one another. (i)
cancelling of
symmetrical
trihalobenzene is not always (0
however, all C C
C
non-polar
C CI

(V) (V)
(iv

C
CI
CI
Here.
Hnet = 0
vectorsis (VII
resultant of dipole
17. (b) In 1,2, 4,1 5-tetrachlorobenzene,

In 1, 2, 3
of one another. Nor polar dichloronaphthalenes
cancellation
do not cancel
0 due to all individual vectors
*letrachlorobenzene.
CI
C
dipoles completely.
Cl

Hg + M4 (Ix) (x)
(vi)
CI
CI

A N S W E R S W I T H E X P L A N A T I O N S
255
 DPP-6 Mixed Hydrocarbons
1. (0) 6, 7-dimethyl-1-octen-4-yne 4. ) Parent chain is wrongly nurmberod The correct nunbering: and
() 4, 4-d1chlorocyclohexene name IS
(ii) 3-methyl-1-penten-4-yne
(v) 1-hexen-4-yne
(v) 4-ethyl-5-methyl-4-hexen-1-yne 4 hoxen 1-yne
(v) 2-ethylcyclopropyl ethyne
(i) One of the carbon (C-3) s having five bonds, inpossible The
Br corroct structure and name is
2. (0) () 4
CH, 2-hexen-4-yne
CH,- H, CH-Cc
B
(ii) Benzene ring carbons are wrongly numbered The corocs
numbering and name is
Br
(n) (v)

(V) (vi)
CI
CI
CI
4-bromo-1,2-dichlorobenzene
CH,
3 CH- CH-CH, (iv) Here, benzene is parent with alkyl locant
Butane 2-methyl propane

()
1-butene 2-butene CI
2-methyl
propene 1-(1-chloroethyl)propyltbenzene
5. (c) Triple bond is closer to terminal than double
() bond, nurmbering
Pentane starts from right terminal as:
CH, 2-methyl
butane
CH-c-CH,
CH,
2 2-dimethylpropane B

6-bromo-7-chloro-5-octen-2-yne
6. (d) Correct numbering of parent
1-pentene 2-pentene
2-methyl-1-butene chain and its IUPAC name
6

3-rnethyl-1-butene 2-methyl-2-butene
3-ethyl-4,4-dimethyl heptane
7. (b) Longest chain with
triple bond becomes theboth double and
Hexane 2-methyl pentane
In the given compound, parent chain
all
double bond and triple the locants,
equidistant from terminals. bond are
3-nethyl pentane 2,2-dimethyl butane circumstance, numbering is Indoneinsuch 4-propyl-2-hepten-5yne
alphabetical order, here lower number
locant and higher number to is being given to el
'yne' locant
8. (d) The correct
numbering of parent chain is
2,3-dirnethyibutane
(vi)
CH,-ÐH ßH, CH,-ÞH
Double and triple bond are
is done in equidistant fromn terminals, numberiig
1-hexyne 2-hexyne 3-hexyne alphabetical order,giving lower
Hence, C,-C,aresp'-sp' number to ene
9. (c) The correct
hybricised
lowest possible numbering in the
number to double present case is one that gve
3-methyl-1-pentyne 4-methyl-1-pentyne 4-methyl-2-pentyne bond hence,
CH,
H,H=cH,
3,3-dimethyl-1-butyne CH,
3, 3-dimethyl-1butene

DPP - GENERAL ORGANIC CHEMISTRY

256 AND
HYDROCARBONS
 bDouble bond has preference over
halide locants gven lowest poss1ble
()CT CH,
number Here, numbenng is started
from double bond gving lowest
0( o r pola)
p0ssible numbers to other locants
also Also. if there is onl\y one double 16. (a bc )
bond inside a ng, its positio) need 3-brono tchlorocvclohexene
not be nentioned in the name C C atoos aro at 180 anglo.
CH, CDpolo rnornent of one halfi
11. c) Nunmbering is started trom double bond, Qivma owest CADCOledby othehalf
DOSsible number to other locants (c) CL n(
hence. ()

() CI

4-ethvl-3-methylcvclohexene CI
49 c) A the three locants on bernzene are equidistant, Iwo CI-atoms aro at 180 angle, u
numbering IS
donein alohabeticalorder as 17. (a, b) Firstly, parent chan is wrongly nurnbere urnbeing
should start from ight terminal as tnple bond is at G1 while
double bond is at C-2 on othersido Also halide l0cants should b
written in alphabetical order irrespective ol ther positions

Br
1-bromo-3-cyclobutyl-5-cyclopropyl benzene CI
13.o) The correct numbering and name is 4-bromo-3-chloO3-ponten 1-yne
Rr However, correct number of carbon atoms are taken in parent
chain andcorrect punctuations.
CHa 18. (6) Since, the compound has a phenyl ring. formula can be
splitted as CgH,CzH The locant (C,H,)has two degree of
HgC unsaturation, it may contain a triple bond or two double bonds as
2-bromo-1,4-dimethyl benzene C=C-CHa
14. b c) In alkyne. C=C is formed by two mutually
perpendicular
p-orbitals at each carbon as
CH-C=CH

C
CH=C= CH,

Y
Triple bonding in alkyne
Aiso in a cumulated diene, the adjacent pi (T) bonds are at right Other pOssibilities are
angle ECH ECH

CHa
CHa
ECH
(p) -bonds in propadiene
15. (a. C.d) H,C
(a) Since, benzene ring is planar with all its carbon sp² hybridised, 19. (5) All the starred carbon ies on a straght ne
atorns directily bonded to phenyl ring, here a carbon of CH,
andCl also lies in the ing plane.
) IS wrong because carbon of CH, and CI are sp' i=iH3
hybridised Iphenyl propyne
(C) Its dichlorination results in following three isomers.
CHa CH,CI CH3 CH3 20. (4)

ANSWERS WITH EXPLANATIONS 257

 DPP-7 One Type of Principal Functional Group
narme butt its molecu
1. () pentane-2. 3-diol 6. (c) AIthough, it is a correct IUPAC ular formula
(i) 6-bromo-5-chloro-2-hexanol is CeH,,0. All others (a), (b) and (d) are
names
on based C-Hn0
(ii) 2-propyl hexanoic acid fornula as well as they are correct IUPAC
(iv) ethyl hexanoate 7. (b) Here, the two dipole vectors are at 180° angle and ino
(v) 2-ethoxy heptane directions

(v) 3-ethyl-2-methyl pentane nitrile

(vi) cyclohex-2-enone
(vin) 5-chloro-4-ethyl-2-methyl hexanal =0

Inall other cases, dipole vectors are not at 180 angle,henca

COOH do not exactly cancel each other.
2. ()
OOH 8. (c) The compound is an acid chloride and the usual suftxis
() H chloride. However, this suffix is used only when-COCI is a nar
of parent chain and carbon atom of the functional aroun.
counted in parent chain. Here-C0Cl is in benzene ring wrers
(n) (0V
carbon of the functional group cannot be counted in parent chan
hence (a) is wrong IUPAC name. The suffX name of -
including carbon is carbonyl chloride, hence the compoung
COOH benzene carbonyl chloride.
OH
9. (d) The compound has one carbon containing principal functiora
(V) (Vi) group, numbering starts from the carbon of principal functiora
group. Also, position of such functional group need not to ce
CoOH mentioned in the name as
Rr
NH2 H, CH, H=ÔH oOH
2-pentenoic ac1d

(vii) (vii) 10. (b) The given compOund is an ester which have two parts in the
B
C name, an alkyl part which comes from alcohol and an alkancate
Br part which comes from an acid. The two parts are wrten
CH3 CI
separately in name, alkyl first followed by alkanoate part
(IX) () NH
C CI
Br B

3. ) 3-chlorocyclohexanecarbaldehyde
(0) 3-chloro-5-chloromethyl cyclohexane carboxylic acid
Br
(1) cyclopentane carboxamide Alkanoate
(M) 5-bromo-2-chloro benzonitrile Alkyl
(V) 4-chloro-1, 3-cyclohexanedione 3,3-dibromo-2-chlorobutyl-2-methyl propanoate
(vi) 5-brorno-2-chloro benzene sulphonic acid (In alkyl part, numbering starts from the carbon directly
bondedte
(vi) 4-(2-chloropentoxy) -3, 5- dinethyloctane Oxygen).
4. (c) Compound has two carbon containing principal
functional 11. (c) Numbering starts from carbon
group, that becone terminals of parent chain irrespective of chain group, hence
bearing principal tune
length. Also, the two alkyl locants are equidistant from terminals.
nurnbering is done inalphabetical order as:
CH3
HO
CH3
COOH COOH
5 3,3-dimethyl-1-cyclohexanol
5. (d) All others (a), (b) and (c) are correct 12. (d) Preference is
IUPAC names and given to hydroxy groups (principal functional
molar mass of 86. Although, (d) has molar mass 86, the have group) first followed by the lowest
number series as
incorrect as per lUPAC convention name is
Br Br
HO
HO

2-methyl butanone CI C
3-methyl butanone
(Wrong IUPAC name) (correct IUPAC name)
OH
Halicdes are at 4,4,6 OH
Halides áre at 4,6,6

nDD - GENERAL
258 ORGANIC CHEMISTRY AND HYDROCARBONS
 Used for
4 2 SutIN s replaced
CHO when ts carbon CHO 19. (a,b,c.d) Halogen Is ie one hydrogen IS C,H,0CI
monovalent
hydrocarbon of
spart ot parent chain
atom by one halogen atorn Hence, the base
CHO is o
IsC ,H¡ Which indicates presence of one dlegree ==0
Here the group duye to C orG =0
the part of parent Unsaturation. The unsaturation can be
vooherane a offerent
3 44-trichiorocyclohexane carbaldehyde
bonding Hence
carbaloehyde
s2d which include carbon of-CHO
Is dehydration product of
40anhyaride C H
carboxylic acid, they
cannot have emoirical formula CarbOxylic acId and
sane
esters 3-chlorobutanal
Butanoyl chloride
r nasec on same empincal tormula C,Ho.0, Aldehyde and
tnes are baseo on same empirical formula CH,.O Alcohols
athers are based on same empirical formula CH. 0 CI 4 C

. monocaroOrylC aCIa, numbering always starts from carbon OH

1-chloro-2-butanone 1-chloro-3-buten-2-ol
-00OHgroup
. Ds1on of chlonne S incorrectly mentioned. It is correctly as: 20. (a,d)
(a) When carbon containing princIpal functional group is directly
on a ring, normal suffix (here -oate) cannot be used In present
case, carboxylate suffix should have been used and correct
IUPAC name would be "methyl cyclohexane carborylate
(d) When there are two carbon containing principal functional
groups (now COOH), their carbon atons become terrninals
of the parent chain irrespective of chain length. The correct
name of this compound would be 2-butyl-4-ethy!
2-chloro-1,4-cyciohexanedione pentane-dioic acid.
(b) and (c) have correct IUPAC names mentioned as
17. The compound is an amine, the CL
oncpa functional group does not
ontan oaroon, preference is given
nnumoeng to the carbon bearing (b) 4 NH2
Sun oroup Also. if a locant is also
Dresent on the nitrogen, its position N Br

s oenoted by N and this "N IS 5-chloro-N-ethyl-2-hexanamine 4-bromo-3-chloro hexanamide

Teated as numeral

18. 2cd Botn carboxylic acid and ester have same empirical (c)
iomuaC-0, Hence. CH,can be an acid or an ester.
2-ethoxy pentane

COOH
21. (b,c) The correct numbering of parent chain is

Buranoc acd (Czt,Oz) Ethyl ethanoate (CH;O)

'CH, 2 3

CHNc CH,-H,
CH, CH3
.OCH3 H
H
It has only three methyl locants, two on nitrogen and one at C-2
Hence, its IUPAC name is N, N, 2-trimethyl-2-butanamine
Butandial (CHO,)
Metny propanoate (CHsO2)

DPP-8 Compounds with One Type of

Principal Functional Groups
1.
COOH LCOOH

(vi) OCH3 (vii) -CH3

COOH
OH OH
COOH (Ix) CçHs-C--CH, (x
(iv) HOOC-CH, -H-COOH
~COOH
HOOC H
OH
COOH NHCOCH3
(Xi) (xi)
OH LOH
CHO
Ho
(9) CHa-CH COOH Vi)
(xIn) HOOC CH,- -CH, COOH
COOH

ANSWERS WITH EXPLANATIONS 259

 2. (0) 1, 1. 4-pentanetricarboxylic acId 8. (b) It is a diester with ethyl as alkyl group in both ester group. Also
numbering woulcd start from carbon of one of the ester group
(1) cyclopentyl cyclopentane carboxylate other locants
() 4 4-dichloro cyclohexane -1.3-d1carbonitule qiving lowest possible nurnbers to
CH,
(Iv) 4-cvclohexene.1. 3-dicarbaldehvde
(v) cyclopentane carboxvlic anhydride C,H,0
(v) 3-ethyl-2, 2-d1methyl oxIane
(Vn) 4-cycloheptene-1. 3-d1sulphonic acd Br
(v) 3-cyclopentyl-2 butanol Diethyl-4-brorno-3-chloro-3-rnethyl heranedioate

(IX) 3-bromophenyl ethanoic acid

(x) 3-brono-5-chloro benzonitrile 9. (d) As the narne suggests, cyclohexyl locant is present on rhck
locant which in turn present at C-3 of butarnarnide
3. 0 Preterence is to be given to hydroxy (principal functional)
group The correct name would be 4-ethyl-3-hexanol. 'CHs
(0 Same as in () Correct IUPAC name would be 4-hexen-3-ol.
(u) The longest chain is not taken as parent chain. NH2

Cyclohexylrmethyl

10. (a) The structure oeinnamaldehyde 1

4-propoxy heptane
H-H-CHO
(N) Numbenng of parent cyclohexane ring is
incorrectly done. It is 5,5-dibromo-2-chlorocyclohexanol.
(v) Here -CN is directly present on ring, it cannot be named 3-phenyl propenal
nitrile because this suffix name exclude carbon of CN
group Including carbon, suffix name is carbonitrile and the Allcarbon is sp hybridised.
correct name would be 3-chlorocyclopentane carbonitrile. It is polar due to CHO group.
4. (c) When more than twO carbon containing principal functional It is phenyl substituted aliphatic aldehyde.
groups lies directly on a single chain, longest chain containing 11. (a,b,d) lt may have the following structures.
maximum number of such groups becomes parent chain.
Priority is given in numbering.
NC CN
CHg-CH¡-CH,- -CH,
Butanoic propanoic anhydride

CH,- H- -0- -C, H,

CN 2-methyl propanoic propanoic anhydride
Here, suffix for the whole CN, 1.e. carbonitrile would be used. It is also a mixed anhydride as it is made up of two different acas
Hence, 2-methyl hexane-1, 4, 5-tricarbonitrile. It cannot be an isomer ofa dioic acid because dioic acids have
four oxygen atoms in a molecule.
o,booH
5. (b) Gluteric acid is H, 12. (b, c, d) C-1 is sp, C-4 and C-5 are sp and allother carbons ae
CH,COOH sp° hybridised. It is a terminal alkyne, Hat the sp-carbon is aso
Pentane-1, 5-dioIC acid
neutralised by NaNH,:
6. (b) Cyclopropyl ring with -OH functional group is parent and
cyclohexenyl ring is locant. ,COOH

2-ethyl-4-hexynoic acid
HO
13. (a, b, c) All the compounds (a), (b) and (c) are correctly nameo
2-(2-cyclohexenyl) cyclopropanol and have the same molecular formula C H0,
Here, position of OHisnot nentioned in the name because it is
understood that numbering starts frorn that carbon where-OH HO
is present. OH ~OH
Sp sp Butanoic acid (C_laO) 2-butene-1,4-diol (C.HsO2)
7. (c)
Sp
N=CC=
180° 180°
OCH3 H.
Ethanedinitrile
H

Hence, all the atoms lies on the same straight line and dipole Methyl propanoate (CaHeO) Butanedial (C4H60)
vector by one CN is exactly cancelled by the other CN group.

DDP - GENERAL ORGANTG CHEMISTRY AND

HYDROCARBONS
260
14 (a, b) Since,COOHis on ing, simple sutlix-OIC acid would not 18, (9) When this i compound is nurnboredcorrectly as surm
of position
ork Suffix carboxylic acid would be used.
if
nnal tunctional group on ring, its position is there is only one
not mentioned in
of two chlorine atoms is
4 + 5- 9
the ring

Dnsition of two chloine atoms are correctly mentioned and the

compound is polar CI

.r iA COOH is directly on cyclopentane ring, its correct IUPAC

aame would be 3-chlorocyclopentane carboxylic acid.
C
iDouble bond has no preference over triple bond. In the given
dnc acid, both double and triple bonds are equidistant from 19. (8) All three carbon of three - COOH are sp
terminals, numbering has been done in alphabetical order where Three oxygen, one in each-C0OH are sp
'ene comes before y of 'yne'
COOH
47 (7) Compound CH;0 is based on general formula C,Hon. .0
Hence, it can be an alcohol or ether.

COOH
HOOC

Ethers 7-ethyl-3-nonene-2,5,8-tricarbOxylic acid

OH
Both C-3 and C-4 carbons are so
OH 20. (6) (0), (), (v), (v), (vi) and (x) can be non-polar. (), (vii) and (vin)
Alcohols are always polar.

DPP-9 Compounds Containingmore than One Type of

Principal Functional Group-l
1. 0) 4-chloro methoxy benzene () -OH has higher lUPAC priority than -NH
OH
(0) 5-bromo-2-chloro benzoic acid
(ui) 2-chloro-5-ethyl benzonitrile NH2
(N) 3-ethyl-5-hydroxy benzonitrile 1

() 3-bromo-5-cyano benzene sulphonic acid 5-am1no-2-pentanol

(v) 5-hydroxy-4-methyl-2-(1-methylpropyl) pentanoic acid (üi) Carbon of -CHO is a part of parent chain.
(vn) 6-0X0-4-(1-0xQethy) heptanoic acid H
(vin) 7-oxOOctanal
OCH3
CHO
2 NH,
LOH
()
(u) Methyl-4-methyl-5-oxopentanoate
OH (iv) Carbon of -CHOlinked to C-atom of cyclohexane ring is not
CI a part of parent ring.
OH
OH OH
HOOC
(v) H

OH OH CHO
3-0X0cyclohexane carbaldehyde

(v) Including carbon CHO gives the longest chain with

HO maximum groupS on it
Vi)
CHO

NH,
(vin)
(x) HO. 5-methyl-6-0xohexanam1de

() Both Cl and Br are al equal d1stance from COOH,

HO COOH |CN numbering is done is alphabetical order
3 by acyl group. COOH
) Alkylgroup of ester is written first followed

OCH3

B
Methyl-4-oXopentanoate 3-bromo-5-chlorobenzoic ac1d

ANSWERS WITH EXPLANATIONS

261
 4. (b) Aldehyde has higher priority than hydroxy group, hence suffix
of aldehyde and prefix of hydroxy is being used. Also, once (b) C H,-O-C-CH4

priority is given to-CHO, remaining groups are treated similarly. Phenylethanoate

i.e. no secondary priority is given.
CHO (c) C H , - C H , - 0 - C - H

Phenyl methyl methanoate

HO
ester with the
AlI above mentioned Compounds are
molecular formula CpH,0,. However, ethyl benzoate has forrmue
compound
CoH,,0,, it cannot be the narne of given
11. (d) Armide has higher priority than cyanide Also, a group at
2-bromo-6-hydroxy benzaldel1yde
position 'N
Here, bothHand- Br are at equal distance from CHO, nitrogen atorm of amide is indicated by
numbering is done in alphabetical order. NH

5. (b) Cyanide has higher priority than hydroxy group. Secondary

priority is notgiven, hence lowered number series 1,2,5 is correct 6

one not the 1.3. 6.

OH CN
5-cyano-N,3-diethyl hexananide

12. (c) Cyanide has higher priority than hydroxy group. Also Cianre
aroup contain carbon, numbering could start trorn this carer
CN Starting from carbon of cyanide, longest carbon chain woud -.
the parent chain as
B
2-bromo-5-hydroxy benzonitrile

6. (c) Acid functional group (COOH) has the highest priority.

Remaining groups are named giving preference to smallest
number series as OH 'CN 1-hydroxy propy!
NH2 4-hydroxy-2-(1-hydroxy propyl)hexanenitrile

13. (b) The same longest chain is obtained on either side of crarc
but going on otherside gives lower number to the douDle con
as:

COOH
1,3 4 is the correct number series not the 1, 4, 5. Therefore the coOH
correct IUPAC name is 4-amino-3-propoxy benzoic acid.

7. (d) 3-(2-propenyl)-4-hexenoic acid

8. (a) The given compound is an ester of ethanoic acid and a Here, double bond of parent chain at C-4 whereas in the gve
substituted phenol. name,double bond is mentioned at C-5.
B
14. (b) Amide has higher priority than hydroxy group. Hence
Br CONH2

CHg
HO
CH3 3-bromo-4-hycroXy benzamide
5-bromo-2-rnethylpheny Ethanoate
in
(alconol part of ester) (acid part of ester) Amide of benzoic acid js given a fixed name "benzamce

IUPAC.
9. (b) The cormpound and correct numbering of parent chain is
COOH 15. (d) CN has higher priority than hence the phen
OH group, both
ing.
ring containing CN is the parent ring In the locant hence
-OH and - Br are equidistant from the branch point. t number

numbering is done in alphabetical order giving lowerr

bromo substituent as:
CN
Br.
6-cyano-2,5-dirmethyl heplanoic acid

10. (d)
5

(a) Cg H C - 0 C H ,
OH CN
Methyl benzoate 3-(3-bromo-5-hydroxypheny) benzonitrile

DPP - GENERAL.
ORGANIC CHEMISTRY AND
262 HYDRoCARBONS
 carbon

’(p): (n)’(r.s). (i1)’ (r s). (iv) ’ (q,s) chain has

sX

6. (a)()- (ii) Name ending with nilrile and parent

) Name end1ng with anoic acid and parent chain has seven
atoms
carbon atoms
COOH

OH COOH CN
4-formyl benzonitrile
6-hydroxy-2-methyl heptanoic ac1d
the parent phenyl r1ng has
Name ending with nitrile and parent chain has six carbon (M) Name ending with suffix nitrile and
six carbon atoms.
atoms
CN

6 OHC
4-formylbenzon1trile
2,4-diethyl-5-oxohexanen1trile

DPP-10 Compounds Containing more than One Type of

PrincipalFunctional Group-ll
when carbon atom of COCI is
butanal I. (c) -oyl chloride suffix is used
1. 0 2-bromo-3, 3-d1methyl COCI is on ring, it is named as carbonyl
part of parent chain. If
o) 2-methoxy cyclopentane carbaldehyde chloride.
(n) 6-pheny-3-propyl-2-heptanone
chloride
diacid chloride and the acid
IV) 3-chloro-2-cyclohexenone 8. (a) The given compound is carbonyl chloride suffix
present on ring, hence
( 4-ethoxy-5-hydroxy-2-hexenal
groups are directly
wOuld be used.
5-dione
(v) 6-chloro-3-isobutyl heptane-2,
iva) 4-methyl-5-Oxohexanal

(V) 2-ethoxy-4-phenyl hexanal

OH
CHO chloride
2-hydroxy-1, 4-benzene dicarbonyl
2.
priority than ether group. Also,
C
9. (a) Acid chloride group has highergroup, the ether group is also
there is a chloro locant in ether
numbered besides the parent chain.
C

)HO0C (iv
Br Br
5-(2-chlorobutoxy) pentanoyl chloride
and C-2 of parent
twomethoxy groups at C-1
C)Tisa diether with of ether branch is done starting
from carbon irectly
Numbering
ethane
bonded to oxygen.
higher prior1ty than amide group. higher priority than keto group
9. (C) Carboxyl1c acid aroup has 10. (c) Here, amide group has
coOH is the principal functional group and later is a
therefore former
H,N chain starting from carbon of the
locant. The longest carbon parent
parent chain. Hence, in fact
amide group would be the
4-amino-4-Oxobutanoic acid as:
chain has eight carbon
than ester
COOH has higher priority
J. (b) Acid functional group
hence.

CH,CH,-coOH
N-ethyl-5-(1-oxoethyl)
Correct IUPACname would be
octanamide
3-(benzoyloxy) propanoIc acid
group and
11. (a,c) The COOH group is principal functional
part of parent chain as
carbon ofCHOis als0 a
CI
C =benzoyl
|CH5 coOH
H
6 on locant Hence,
*)nere, we have locant Br
2-bromo-2-chloro-3-formyl propanoic acid

o-CH,j CHO is not locant on

parent as its carbon is part of
parent

Methoxy 2-methOxy ethoxy chain.

A N S W E R S W I T H E X P L A N A T I O N S
263
 12. (b.c) Cyanide has higher priority than hydroxy group, hence suffix compound is
18. (4)The structure of given
of the name would be nitrile. Other two locants on the parent ,CH3
phenyl ring are equidislant from CN, numbering is done in
alphabetical order as
OH
OH

carbon ,
Only hydrogen atorns attached to sp hybridised
CN can be coplanar. Labelled hydrogens are coplanar
3-(3-chloropheny) 5-hydroxy benzonitile
19. (6) The six isormers of given cornpound are
Chlorophenyl conmes betore hydroxy in alphabetical order, given CN CN CN
lower number on parent ring.
-CN CN OH
13. (ab.d)
OH
OH CN
COOH COOH
3-hydroxy butanoc acid OH
3-methoxy propanoic acid
CN CN CN

COOH
Ethoxy ethanoc acid 4-0xobutanoic acid (CaHO)COOH
CN HO CN OH
Only 4-Oxobutanoic acid has different formula, remaining three
have the same given molecular formula and valid IUPAC names OH CN
as indicated.
All the above mentioned hydroxy benzene dicarbonitrile nae
14. (a,c.d) Given compound is athree membered cyclic ether which different IUPAC names.
is known as oxirane in IUPAC system. Numbering starts from
Oxygen atom. 20. (8) Possible four carbon acids are CH,CH, CH,COOH aro
(CH),CH-COOH. Possible four carbon alcohols are

3-ethyl -2, 2-dimethyl OH OF

Oxirane (an epoxide)
OH
15. (b.d) Here, COOH has higher priority than ester group, hence
the compound is an alkanoyloxy acid, not a carboxy ester. Also,
Therefore, each acid on pairing with four different alcohols gives a
total of eight esters as:

4-butanoyloxy-2-methyl pentanoic acid

As locant R-C-is named as alkanoyl. (1

16. (5) Since, the compound has a phenyl ring, formula can be
splitted either as CH(0CH,) or C,(OH) CH). The
Corresponding compounds are (1)
CH3
CH,OH OH (iv)
0CH,

Methoxy benzene Benzyl alcohol 2-methyl phenol

CH, CH,
(vi)

OH
3-methyl phenol (vi)
OH
4-methyl phenol
17. (5) The given compound is
(vii)
CHg OH

+OOH All above mentioned esters (i-vii) have different IUPACnames.

Starred carbon atoms are sp hybridised.

DDP - GENERAL ORGANIC CHEMISTRY AND

264 HYDROCABBONS
 Revisal Problems (JEE Main)
1. (d) CzH,
has two degree of
unsaturation which may be found in the
form of two pi()- bonds or in the form of cycloalkenc. Possible 5. (d)
Compounds are
H
H
heptane
H-CC=0-H 3 ethyl 4 isopropyl2 5dirnethyl
frorn terrounals of parent chair
O. (b) Locants are cquid1stant alphabetical order
Propyne hence, numbering is done in
Propadiene

3-ethyl-4-rnethyl hexane

alkyl locants Herce

yclopropene (. (c) Double bond has preference over
lowest number is given to double bond
Davne has one so and twO sp hybridised carbons. Propadiene has
t and C-3 sp while C-2 is [Link] both propyne and
oron2diene the three carbon atoms lies on the same straight line.
HOWever. none of the above has allthe hydrogens present in the same
1,3-d1methyl cyclohexene
piane.
2 b) Since the functional grOup (ester) containGarbo and it is directly 8. (c) Double bond has
presenton cyclohexane ring, carboxylatfather than'siple oate suffix preference over alkyl group.
WOuld be used as Hence, lowest possible

number is given to double

-heotene
CH,000-4 -COOCH3 bond and the longest chain
4-cyclopropyl-4-ethyl-1

Containing double bond is

Methyl cyclohexane 1,4- dicarboxylate
chosen as parent chain.
carbon in the straight chain than
bonds becomes the parent 9. (b) An open chain has more
3. c Longest chain with maximum double the number of carbons in ring, ring becomes locant and
series are obtained from both the terminals
chain. Here, same number open chain becomes parent as
2 4,56) hence, ethyl is being givenalphabetical preference.
CH, CH

4. c CHC-CH,’ CHg-CCH, Ci 2-cyclopropyl-3-methyl butane

CH3 equidistant from terminals

CH, Also, the two locants are
Monochlorination numbering follow alphabetical order.
22-dimethyl propane
(unsaturated alcohol) al have
CH,CI 10. (d) Aldehyde, ketone, alkenol
CH3 satisfy C H, (general formula for all
one pi(r) bond, hence
>CH5-CCHCI, + CHÇ-CH,CI of them is C,Hn-50. General formula of a cycloketone is
CHgn-20, does not satisty CgH,o.
H dialdehyde and a
CH, 11. (d) Unsaturated, acyclic carboxylic acid,
Only two dichlorination products diketone, all have two pi() bonds each, hence based on
any
general formula C,H¡n-0, Therefore, CsH,0, can be However an

O-OC above mentioned compounds.

of the
would be
unsaturated acyclic diolwith only one double bond
satisiy
Cyciooctane Monochlorination based on general formula C,H,O, does not
CI
CpH,
+
12. (d) 4 CH3,
CI
Five dichlorination products 10

CH, ÇH 5, 6-chethyl-3-methyl decane

CH,-CC CH,--Cl’ COOH or other Such group, which contain a

CHg-C CH, 13. (d) When
simple suffix like
CH, CH, carbon, IS present cdirectly on a ing. their
CH, CH, Monochlorination
oic acid cannot be used. The suffix narme of -COOH
2, 2, 3, 3-tetramethyl butane carboxylic acid. Hence, correct name of
including carbon is
the given compound is
CH, CH, CI CH, CHs
CH, CH3
CH,
CH,-c¢-CHC; +CHy CH, CI +CH -COOH
CH, CH,
CH, CHg CH, CH, 2-cyclohexene carboxylic acid

Three dichlorination products

ANSWERS WITH EXPLANATIONS

265
 14. (b) Here, cyano is the
principal
priority than hydroxy group. Alsofunctional
Cl and
group as it has higher 22. (b) Hore, cyarno group S principal functional lgroup.
prctereCS I,
trom the principal functional aroup, OHare equid1stant (iven to therm in nunboring
alphabetical order as numbering would be done in

NC

C 1CN
[Link] benzonilnle
CN
15. (c) Here, sulphonic acId is the pincipal 4 ottylcyclopontane 1,3 dicarbonitrile
functional qoup heote and
the wo substituents (B1 andCI) ate cquidistant
from the ptincipal 23. (b) SO,H is principal functional group bJT Gquidistant fro
functional group, numbering would be done in alphabetical order
slarting from principal functional group tominals, Henc0, nurnberingis done in away which qves lu
R number to double bond als0

HO,S
SO,H
CI SOH
6 30ctene-2, 7-disulphonic acid
3-bromo-5-chlorobenzene sulphonic acid
16. (b) It has more than twO SiMilar
Contain carbon
principal functional group which
24. (b) Br-- CH,-C-NHBr
The longest chain (excluding principal N, 2- dibromo ethanamide
all -COOH are present would be functional group) on which
the parent chain as
ÇOOH If a group is present at nitrogen atom, its position is indicated u
N,
HOOC
25. (d) The given compound is a ketoester. Since, ester has hicrer
IUPAC priority than keto group, suffix of ester and prefx of ketr
group would be used as:
OOH
5-ethyl-1,3, 6- hexanetricarboxylic acid
17. (b) Here. the principal functional group here
Hc 0CH,
5
is ester which is
derived from a substituted benzoic acid and
parent name wouid be ethyl benzoate.
ethanol. Hence, the
Methyl-4-oxohexanoate
26. (c) Acetonitrile is a common name of ethanenitrile
which has so
and sphybridised carbon atoms only.

COOCzHs
Ethyl-3-chloro-5-ethyl benzoate sp sp
18. (a) Cyciopropanoic acid is an incorrect Allothers haveC=0 group in which carbon is sp
lUPAC name because hybrid1sed
carbon of -COOH is not included in the name. The correct CH, CH,
name of this compound would be cyclopropane
carboxylic acid. 27. (a) CH,-H H-CH¡
19. (c) The hydrocarbon C; Hp is based on general 2, 3- dimethyl butane
formula C,H2n+2 Carbon atoms are either primary or tertiary but
hence, it does not has any unsaturation. On the other hand,
no secondary.
cycioalkne is based on general formula C, Hn With one degree ofa
unsaturation. Therefore, C H cannot be a cycloalkane. CH,
Also, it is completely saturated, therefore all its
carbon are sp
28. (c) CH,-H-0-CH,--CH,:
nybridised. The smallest chain would be found in 1-ethoxy-1- methyl ethane
propane with only three carbon in parent chain. In this2,2-dimethyl The indicated name is wNrong according
is quaterrnary, i.e. not bonded to any isomer, C-2 to IUPAC because a
hydrogen atom. longer propane chain is present. Correctly, this
20. (d) Parent chain taken here is not the longest be named as 2- ethoxy compound would
possible propane.
carbonch¡in present in the compound would be the chain. Asix 29. (d) Three carbon containing
as:
parent chain principal functional groups On à
chain. Hence, longest chain
which ali three excluding carbons of CN, on
CN are present would become the parent chain.

cOOH NC CN
4-chloromethyl hexanoic acid CN
21. (d) The open chain has more carbon 1,2, 3-propane trinitrile
than ring and both contain one 30. (d) The longest chain has four
carbon
ketone functional group. Therefore, name cannot ends in propane, rather itatoms. therefore its IUrr
chain would become parent and ring always ends in butane.
OH
locant as:
3-(2-0xocyclopropyl) butanone CHa-CH-CHCH,
2- butanol

DDP - GENERAL ORGANIC

266 CHEMISTRY AND HYDROCABBONS
 Revisal Problems (JEE Advanced)
The correct numbering of given compound is 7. (a, d) C
1. (c)
-CHa

2-cyclohexenone
H,C Position ofC=0needs not be nentioned.
Numbering starts frornC=0 as it
is the principal furctional group.
douole
4-ethyl-6-methyl-2-cyclohexenone clockwise direction in order to aive lower nurnber to
goes in
0is principal functional group, numbering starts here. bond.

Gong counter clockwise, tind locants at C-2,C-3 both, whereas (b OH

fwe ao clockwise, locants would be found at C-2 and C-4.
order.
Locants name are written in alphabetical
CH3
Pos1tion o f C O needs no specification.
hence it is phenol derivatve
2. (b) The highest priority group
here is COOH -OH is the principal functional group,
COOH. S1nce, no secondary priority not toluene derivative.
Br phenol. meta-methyl can also
be
treated
$ given, other groups are Correct IUPAC name is 3-methyl
6

similarly. used. CN
~CONH2 -OH group hence,
is the prefix name of (c)-CN has higher priority than
A

Carbamoyl benzonitrile not

CONH, group. the compound is hydroxy
1,3,6.
Here. number series 1,2, 5 has been preferred over cyanophenol.
benzonitrile.
-COOH is directly on ring, carboxylic acid rather than -oic Correct IUPAC name is 3-hydroxy
meta-hydroxy can also be used.
acid is being used. sulphonic acid.
methyl ester of benzene
COOH (d) Given compOund is a
hence the given name is correct.

8. (c, d) than -CN.

-S0,H has higher priority
(a) has correct name as ethanoic acid
cONH, an ester of phenol and
(b) has correct name as it is correspond to
2-bromo-5-carbamoyl cyclohexane carboxylic acid mentioned as benzyl
(c) has Wrong name be phenyl
Br ÇOOH CsHs-CH, The correct IUPAC name would
given
3. (b) The correct numbering of CI benzoate.
Compound is as follows:
wrong name mentioned as - OH has higher priority than
-COOH is here the functional group (d) has would be
-NH, group. Its correct IUPAC
name

of highest priority. 3-amino-5-bromophenol.

ester
Ethoxy carbonyl is prefix for the has following structure
9. (a, b) The mentioned compound
locant. parent chain as it
Carbon of ester aroup is
not considered in 4 7

Would give a parent chain of

six carbons only.
H 3 -CH,
cyanide. Hence,
functional aroup here is
4. (d) The principal cyano groups as:
here to two locant at
lowest numbers are given at terminals and one as
OH
It has three methylgroups, twO
C-5.
CN C-2,C-5 and C-6 are sp hybridised.
has 5sp hybridised carbons
It has no ethylgroup. Also, it
compound has following
structure
10. (a. b, c). The mentioned
CN
4-hydroxy benzene-1, 3-dicarbonitrile

compound is as:
numbering of the given
O. (c) The correct IUPAC
and only two C=0) sp² hybridised
It has only one methyl group
H,c CH carbon atoms.
same
have same number of carbon,
terminal than double bond. Since, both ring and chain parent and
Iriple bond is closer to available position for the keto group, ring would be
Hybridisation at C-4 is sp while
that at C-5 is sp. to alphabetical order
chain would be locant due
is compound would
numbering of the given compound has higher priority than hydroxy,
b. (a) The correct 11. (a, c). Cyanidecorrectly as:
HO C be numbered

coOH
3-chloro-5-cyclohexyl-6-hydroxy-5-methyl-3-hexenoic acid three carbon
Parent chain has only
priority. name would be
functional group of highest Correct IUPAC
COOH is the principal 2-(1-hydroxycyclohexyl) propane nitrile.
carbon atoms.
Longest chain has 6
267
A N S W E R S W I T H E X P L A N A T I O N S
 20. (d) Propenal has two degree of unsaturation, one due to C
12. (a)
aldehyde
(a) Numbering would start from carbon where two methyl groups bond and other due to (C=0) bond of
are present and the name would be 3-ethyl-1, 1-dimethyl 21. (b) 2-methyl Oxirane
1

cyclohexane
(b) It has correct name
(c) It has correct name, carbons of two -CN groUps are CH3
2-methyl oxirane
terminals of parent chain
(a) It has correct name asOH is the principal functional group 22. (d) Numbering starts from oxygen in case of oxirane. Hosee
the number series with smaller number at first Occassion of
with equidistant ethyl and methyl locants. Numbering is done
in alphabetical order starting from carbon bearing OH difference willbe the correct one as:
group

13. (c. d)
H,C
(a) Mentioned name is incorect, carbon of CHO is a part of
The Correct IUPAC narme of this Compound
parent chain as it gves longest chain with more number of
locants on it The correct IUPAC name would be 3-ethyl-2, 2-dirnethyl oxirane.
4-methyl-5-0NOpentanoic acid. COOH group has higher Br
OH 23. (a)
(b) The mentioned name is wrong as it has than -CN, hence
smaller parent chain, The correct name priority
numbering is started from the ring NC? cOOH
WOuld be 2
HO carbon where -COOH is present. 4-brorno-3-cyano benzorc ar
(c) and (d) are correctly named. 2-ethyl-1,4-hexanediol sp sp
14. (6. d) 24. (a)
(b) in butadiene, there are more than one combination of position 180° 180°
of double bonds are available. Hence, position of double Allatoms lies on the same straight line.
bonds must be specified in the name.
(d) The position of two hydroxy groups must be mentioned in the 25. (d) Bromine is not bonded to sp² hybridised carbon, rather t s
name due to same reasons as in case of (b). bonded to sp hybridised carbon atom.
15. (a b.d) The structure of given compound is Starred carbons are all sp hybridised
CH3 CHg
CH3 Chs -OOH
CHs CHa CHs Br
CH, H3 (2-bromo-3, 5-cyclohexadiene carboxylic acid)
As shown in the structure, it has two isopropyl groups, 9 methyl 26. (a)
groups. However, there is no ethyl group present
CH-CHO
16. (a.b.c.d) Cyanobenzoic acid is COOH
The six ring carbon and a carboxyl carbons are sp Ether Alkanal
hybridised
CH, =CH CHO
Carbon C=Ngroup is sp hybridised. CN
-CN can take three different positions v0z-ortho, Ether Alkenal
meta and para.
No carbon is sp° hybridised.
(i) CHz=CH-0CH, CH3-CH,-CHO, CH3C-C3
17. (d) The six different isomers of the given compOund are Ether Alkanal Alkanone
CN CN CN

C C (iv) Ether

’ (p.q), (i) ’ (p,s). (ii) ’ (p.g,r). (iv) ’p

CI
CI
27. (b) (0) ’ (p, , s)

CN CN CN H Hy
-C=N
C H
H

All atoms are coplanar Cand N are coplanar All atoms are coplanar
CI
V VI
(i) ’ (p, s)

18. (c) The structure IV is most polar as the resultant of two C-C|
dipole vectors would be aligned with CN dipole, would be
P:
added giving maximum dipole moment. -0 (non-polar) =0 (non-polar)
(ii) ’ (p, 4, r, s) : All of these have atleast one oxygen or ole
19. (d) The structure VI is least polar because the resultant of two nitrogen atom which contain lone pair of electrons.
C-Cldipole vectors would be at 180°angle to -CN dipole and
in opposite direction.
(iv) ’ (p, q, s) : ln propyl nitrile, there is only one lone par
nitrogen. In all other case, two lone pair of electrons are presenta
each oxygen atom.

DDP - GENERAL ORGANIC CHEMISTRY AND

268 HYDROCARBONS
 ifforont
() ’
(9);GnHerO isS general formula of saturated will havo
alCohol as 31. (9) lotal nino DOsiloal inornOrs oxist
wuch
28. (a)
well a s e t h e r s

() ’ p) C,H0is general forrnula of aldethydes, ketones,

unsaturated.
and ethers, cyclic ethers and alcohols, otc
alcohols CI
(W
( . s).C,H2n -202has two degree of unsaturation plus two () CI
Oxygen atoms Hence it can be a dialdehyde, diketone or an
unsaturated acid

(t): C H , has one degree of unsaturation plus two (iv)

oxygen atoms Hence, it can be a carboxylic acId, an ester, ctc (i)

(p, q, s) C
29. (c) () ’
(V) CI
(ú) CI

C
(vill) CI

.nas 3 N-atom Parent chain has SIX Carbon It has C-4 andC-2 (vi) CI
tertiary c a r b o n

() (q. r) CI

(ix) CI
CN CN
tho ono indicated in the given
nas no tertary Natom G-2 and C-4 are tertiary carbon. Parent 32. (8) Ithas a further longor chain than
chan has 5 carbon
narme,

(i)- (p, r)

is nitrogen is tertiary. Parent chain has five carbon Given: 3-(1-butenyl)-1,5-hexadiene

(iv) ’ (a) It has two tertiary carbon. Parent chain has only two IUPAC :4-ethenyl-1,5-0ctadiene

carbon
,cOOH 33. (9) C

NH,
CI
30. 4CH;-CH,-CH,-CH,-ÕH,
1,3, 5-trichlorobenzene
-0-CH, CH0 CH,
1-ethory-3-(2-methosy ethosy) propare Surm of the position nurmber is 1+ 3+ 5 = 9
The above shown compound has fourCCbonds.

JEE Archive

5. (d) CH,H-CH,
1. o Neocentane H,ç-cH,
CH, 3-rnethyl butan-2-one or 3-rnethyl-2 -butanone
IUPAC narne is 22-dimethyl propane
2. 13 Keto (- ) functional group is given priority
3
6. (0) incorrect 4

nurnbering
CH,-CH-CHCH,
1
3-ery-4 4-drnetry neptane Correct numbering
CH, OH functional group
should be given
3. c Correct narne 3-methyl butan-2-ol
priority
or 3-rnethyl-2 butanol

7. (c) CeH, C CI: Benzene carbonylchloride

OH
8. (b)
saturaton oouble bona, s aven prorty Gver nalogen So
the
orrePAC rannes 3-ororno-1-cniorocyclohenene

4. CN
Br

Sgen C. thus it S CN nas the highest prionty

2-bromo-5-hydroxy bernzonitrle
3ery--oycioneao

ANSWERS WITH EXPLANATIONS 269