nomanclature type 1

20 Pages·2011·0.34 MB·English

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Subject : CHEMISTRY
Topic : NOMENCLATURE
R
Index
1. Key Concepts
2. Exercise I
3. Exercise II
4. Exercise III
5. Exercise IV
6. Answer Key
7. 34 Yrs. Que. from IIT-JEE
8. 10 Yrs. Que. from AIEEE
Student’s Name :______________________
Class :______________________
Roll No. :______________________
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IUPAC E
R
U
T
A
Nomenclature according to IUPAC system involves use of following terms: L
C
(i) Word root : The word root represents the number of C atoms in parent chain. N
E
M
No. of C atom W.R. No. of C atom W.R.
O
1 Meth 8 Oct N
0
2
2 Eth 9 Non of
3 Prop. 10 Dec e 2
g
4 But 11 Undec Pa
5 Pent 12 Dodec
6 Hex 13 Tridec
7 Hep
L
(ii) Primary suffix : Primary suffix is used to indicate saturation or unsaturation in carbon chain. A
P
While writing name, primary suffix is added to word root. O
H
m Nature of C chain Primary suffix B
.co (1) Saturated C chain ane 1 ,
es (2) Unsaturated C chain 88
ass C=C ene 58
ocl C≡C yne 30
k 9
e 2 C = C diene 98
w.t 2 C≡C diyne 0
ww (iii) Secondary suffix : Secondary suffix is used to indicate functional group in organic comp. It is added 0,
0
primary suffix by dropping its terminal "e". 0
: 0
e Prefix : The part of the name C appears before the word root is called prefix. Different prefixes are0
bsit used for dif categories of group as: 32
we 5)-
m (a) Alkyl groups: 75
0
fro CH3–CH2–CH2 → 1-propyl H: (
e CH –CH–CH → 2-propyl P
g 3 3 )
ka CH3–CH2–CH2–CH2 → 1-Butyl Sir
ac CH3–CH2–CH–CH3 → 2-Butyl K.
dy P C|H3 → 2-Methyl-1-propyl S. R.
u CH −CH−CH (
St 3 2 YA
d RI
a (b) In IUPAC system,for nomenclature some groups are not considered as functional group but A
o K
l
wn treated as substituent. These functional group are always indicated by prefixes instead of R.
o secondary suffixes. G
D A
E –NO2 Nitro UH
E –OR Alkoxy S
FR –Cl Chloro or :
–Br Bromo ct
e
–I Iodo r
Di
–F Fluoro S,
–N=O Nitroso E
S
S
–NO Nitro A
2 L
=N Diazo C
O
K
E
T
(c) In polyfunctional compound, one of the functional group is treated as principal functional groupE
R
& indicated by secondary suffix while other functional groups are treated as substituents & U
T
A
indicated by prefixes.
L
C
N
E
G.F O.Co. Suffix IUPAC Name Prefix M
O
R–OH Alcohols ol alkanol Hydroxy N
0
R–SH Thioalcohols thiol alkanethiol Mercapto 2
of
R–NH Amines amine alkanamine Amino 3
2 e
R–CHO Aldehyde al alkanal formyl ag
P
RCOR Ketone one alkanone Keto or oxo
RCOOH carboxylic acid -oic acid alkanoic acid Carboxy
Amides RCONH amide alkanamide Carbamoyl
2
Acid halide RCOX oyl halide alkanoyl halide haloformyl L
A
Ester RCOOR oate alkylalkanoate Carbalkoxy P
O
Nitriles R–C≡N nitrile alkanenitrile Cyano H
m B
.co Isonitrile R–NC isonitrile alkane isonitrle Carbylamino 1 ,
es Arrangement : 88
ass Prefix(es) + word root + p. suffix + sec. suffix 58
kocl CH3−C|H−CH2−CH2−OH 8930
e Methyl + but + an + ol 9
w.t CH3 0
ww Rules: 0,
For saturated compounds: 0
0
: (i) Selection of longest chain : 0
e 0
bsit (a) Longest continuous chain of carbon atoms is selected. This is called parent chain while all other32
we C atoms C are not included in parent chain is called side chain. 5)-
m ←→6 75
C−C−C−C−C 0
o (
fr | H:
e C P
kag (b) If more than one set of longest chains are possible, the chainCmax. no. of substituant acts as Sir)
ac parent chain. C−C−C−C−C−C K.
P | R.
dy C−C S.
u (
t | A
S Y
d C RI
a A
o (ii) Numbering of selected chain : K
l
wn (a) The selected chain is numbered from one end to other. The number are called locants. NumberingR.
o is done in such a way that lowest no. is assigned to side chain or substituent G
D A
E 1 2 3 4 5 UH
E C−C−C−C−C S
FR C|H tor :
3 c
(b) If two different alkyl groups or substituents are at same position from opposite ends, lowest no.e
r
Di
is given in alphabetical order.
S,
7 6 5 4 3 2 1 E
C−C−C−C−C−C−C S
S
| | A
L
CH C H C
3 2 5 O
K
E
T
(c) If two different substituents are at same position from opp. ends, lowest no. is assigned in orderE
R
of their alphabets. U
T
A
1 2 3 4 4 3 2 1 L
C
C−C−C−C C−C−C−C N
E
| | | | M
O
Cl I Cl Br
N
0
2
(d) The numbering is done is such a way that the substituted carbon atoms have the lowest possibleof
numbers. Where series of locants conatining the same no. of terms are compared term by term, thee 4
g
chosen series should contain the number on the occasion of first difference. Pa
7 6 5 4 3 2 1 1 2 3 4 5
C−C−C−C−C—C−C C−C−C−C−C
| | | | | | |
L
CH CH CH Cl I CH Br A
3 3 3 3 P
O
m 1 2 3 4 5 6 7 8 9 10 BH
.co C−C| −C−C−C−C−C| −C| −C−C 1 ,
s 8
e C C C 8
ss 8
cla (iii) Arrangement of prefixes : 0 5
o 3
k (a) Side chain or substituent group are added as prefixCits locant in alphabetical order.. 9
8
e 9
w.t CH −CH−CH−CH 0
ww 3 | | 3 2-bromo-3-chlorobutane 0,
Cl Br 00
: 0
e 0
websit H3C−CC|HH−CC|Hl −CH2−CH3 3 chloro- 2-methyl butane 5)- 32
m 3 75
0
o (b) If more than one similar alkyl group or substituents are present then di, tri, tetra are used. (
fr H:
kage C|H3 Sir) P
ac H C—C—CH K.
P 3 | 3 2,2-dimethyl propane R.
dy CH S.
u 3 (
t A
S (c) In case side chain is also branched, it is also numbered form carbon atom attached to main chainY
d RI
a & is generally written in brackets. A
o K
l
wn 3 4 5 6 7 R.
o CH −CH −CH−CH −CH −CH −CH G
D 3 2 2 2 2 3 A
E | UH
E 2 CH−CH S
FR | 3 or :
1 CH t
3 c
e
r
3-ethyl-2-methyl heptane Di
S,
E
S
S
A
L
C
O
K
E
T
E
1 2 3 4 5 6 7 8 R
U
CH −CH−CH −CH −CH−CH −CH −CH T
3 2 2 2 2 3 A
| | L
C
CH 1 CH−CH N
3 3 E
| M
O
2 CH N
3 0
2
2-methyl-5-(1-methyl ethyl) octane of
5
e
g
a
P
The use of iso & related common prefixes for describing alkyl group as long as these are not further
substituted are also allowed by IUPAC nomenclature. While writing name in alphabetical order prefixes
iso & neo are considered to be part of fundamental name of alkyl group. However sec. & tert are not
considered to be part of fundamental name.
L
A
P
CH −CH−CH CH O
m 3 | 2 3 BH
.co C−C−C| −C−C−C−C−C−C−C 1 ,
s 8
e CH(CH ) 8
ss 3 2 8
a 5
cl 3-Ethyl-2-methyl-4-(1-methylpropyl) decane 0
o 3
k 9
8
e 9
w.t For unsaturated hydrocarbon: 0
ww (i) Select the longest possible carbon chain having maximum no. of unsaturated carbon atoms or max. no.0,
of double or triple bonds, even if prior rule is violated. 00
: 0
e C−C−C−C−C−C 0
bsit || 32
we C 5)-
m (ii) Lowest no. is assigned to first unsaturated carbon even if prior rule is violated. 75
0
o (
fr 1 2 3 4 5 6 7 H:
e P
kag CH3−CH2−HC=CH−CH2−C| −CH3 Sir)
ac CH K.
P 3 R.
dy (iii) If double & triple bonds are at same position from either ends, lowest no is assigned to double bond S.
u (
t 1 2 3 4 A
S Y
d C=C−C−C≡C RI
a A
o (iv) If both alkene & alkyne group are present, the org. compound is named as derivative of alkyne ratherK
l
wn than alkene. R.
o CH –CH=CH–C≡CH G
D 3 A
E Pent-3-en-1-yne UH
E In some cases all the double & triple bonds present in molecule can't be included in longest chain. In suchS
FR cases following prefixes. or :
t
CH = CH –CH= c
2 3 e
r
Methylene Ethylidene Di
S,
E
CH≡C– CH =CH– S
2 S
Ethynyl Ethenyl A
L
C
O
K
E
T
For functional groups : E
R
(i) Select the longest possible carbon chain having senior functional group. U
T
A
L
←→ CH −COOH C
C−C−C−C−C−OH | 2 EN
| | CH −CH−CH −CH M
3 2 3 O
OH C | N
| CH −OH 20
C 2 of
6
e
g
(ii) The carbon atom of functional group is to be included in deciding the longest carbon chain. a
P
C–C–CN 3 carbon chain
C–C–C–CHO 4 carbon chain
(iii) The lowest no is assigned to functional group even if prior rules are violated. L
A
P
O
O H
m B
6 5 ||
s.co CH3−CH−CH2−C−CH2 −CH3 81 ,
e | 4 3 2 1 8
class CH3 0 58
o 3
k 9
8
e CH 9
w.t 5 4| 3 3 2 0
ww CH3−C−CH2−CH−CH3 0,
| | 0
0
: CH CH OH 0
e 3 2 0
bsit 1 32
we (iv) The order of numbering a carbon chain, thus follows the order: 5)-
m (a) Functional group 75
0
fro (b) Unsaturation H: (
e (c) Substituents & side chains P
g )
ka 7 6 5 4 3 2 1 Sir
ac C=C−C−C−C−C−C K.
P | R.
dy OH S.
u (
t A
S Y
d 1 2 3 4 5 6 7 RI
a C=C−C−C−C−C−C A
o K
wnl O|H R.
o G
D A
E (v) If more than 1 functional group; then choice of principal functional group is made on the basis followingUH
E order of preference: S
FR O O O O O or :
t
|| || || || || c
e
COOH > SO3H > −C−O−C− > −C−OR > −C−OCl > −C−NH2 > –CN > –NCDir
> aldehyde > Ketone > alcohol > thiols > amines > ene > yne S,
E
S
S
A
L
C
O
K
E
T
EXERCISE - I E
R
U
Q.1 How many 1°carbon atom will be present in a simplest hydrocarbon having two 3° and one 2° carbonT
A
L
atom? C
N
(A) 3 (B) 4 (C) 5 (D) 6 E
M
O
Q.2 C H Br can shows: N
(A3) T6wo2 gem dibromide (B) Two vic dibromide 20
of
(C) Two tert. dibromo alkane (D) Two sec. dibromo alkane 7
e
g
a
Q.3 The IUPAC name of the compound CH CH = CHCH=CHC≡CCH is: P
3 3
(A) 4,6-octadiene-2-yne (B) 2,4-octadiene-6-yne
(C) 2-octyn-4,6-diene (D) 6-octyn-2,4-diene
Q.4 The correct IUPAC name of the following compound is: L
A
P
O=CH−CH −CH−CHO O
2 H
m | B
.co H−C=O 1 ,
s 8
e (A) 1,1-diformyl propanal (B) 3-formyl butanedial 8
ss 8
a (C) 2-formyl butanedial (D) 1,1,3-ethane tricarbaldehyde 5
cl 0
o 3
k Q.5 The correct IUPAC name of compound: 9
8
e 9
w.t CH −CH −C−CH−CHO is: 0
ww 3 2 || | 0,
O CN 00
: 0
e (A) 2-cyano-3-oxopentanal (B) 2-formyl-3-oxopentanenitrile 0
bsit (C) 2-cyano-1,3-pentanedione (D) 1,3-dioxo-2-cyanopentane 32
we 5)-
m Q.6 All the following IUPAC names are correct except: 75
o (A) 1-chloro-1-ethoxy propane (B) 1-amino-1-ethoxypropane (0
fr (C) 1-ethoxy-2-propanol (D) 1-ethoxy-1-propanamine H:
e P
g )
ka Q.7 IUPAC name of: Sir
ac K.
P CH3−|C| −C|H−C||−OCH3 R.
dy O C=OO S.
u (
t | A
S Y
d CH3 RI
a A
lo (A) Methyl-2,2 acetyl ethanoate (B) 2,2 acetyl-1-methoxy ethanone K
wn (C) Methyl-2-acetyl-3-oxobutanoate (D) None R.
o G
D A
E Q.8 The IUPAC name of β-ethoxy-α-hydroxy propionic acid (trivial name) is: UH
E (A) 1,2-dihydroxy-1-oxo-3-ethoxy propane (B) 1-carboxy-2-ethoxy ethanol S
FR (C) 3-Ethoxy-2-hydroxy propanoic acid (D) All above or :
t
c
O e
r
|| Di
Q.9 The IUPAC name of compound CH3−C−CH−CH−CH−CH3is: S,
E
| | |
S
CH CHOCH S
3 3 A
L
C
(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal O
(C) 2-Isopropyl-3-methyl-4-oxo pentanal (D) None of the above K
E
T
E
HO−C=O CH R
3 U
| | AT
Q.10 The IUPAC name of compound CH −C=C—C−His: L
3 C
| | N
E
NH Cl M
2 O
N
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid 0
2
(B) 3-amino-4-chloro-2-methyl-2-pentenoic acid of
8
(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid ge
a
P
(D) All of the above
Q.11 The IUPAC name of the structure is:
H N−CH−CH−CHO L
2 A
| | P
O
HOOC COOH H
m B
.co (A) 3-amino-2-formyl butane-1, 4-dioic acid (B) 3-amino-2, 3-dicarboxy propanal 1 ,
es (C) 2-amino-3-formyl butane-1, 4-dioic acid (D) 1-amino-2-formyl succinic acid 88
ss 8
a 5
kocl Q.12 C4H6O2 does not represent: 930
(A) A diketone (B) A compound with two aldehyde 8
e 9
w.t (C) An alkenoic acid (D) An alkanoic acid 0
ww Q.13 Esters are fiunctional isomers of: 0,
0
: (A) Hydroxy aldehyde (B) Ketone (C) Diketone (D) Diols 0 0
e 0
bsit Q.14 How many carbons are in simplest alkyne having two side chains? 32
we (A) 5 (B) 6 (C) 7 (D) 8 5)-
m 75
0
o (
fr Q.15 Which of the following is not correctly matched: H:
e P
kag (A) Lactice acid CH3−CH−COOH Sir)
ac O|H K.
P R.
dy (B) Tartaric acid HO−CH−COOH S.
u (
t | A
S Y
d HO−CH−COOH RI
a A
o (C) Pyvaldehyde CH C(CH ) CHO K
wnl 3 3 2 R.
o CH G
D 3 A
E CH −C| —CH−CH UH
E (D) Iso-octane 3 3 S
FR C| H C| H or :
3 3 ct
Q.16 Which of the following pairs have absence of carbocyclic ring in both compounds? e
r
(A) Pyridine, Benzene (B) Benzene, Cyclohexane Di
(C) Cyclohexane, Furane (D) Furane, Pyridine S,
E
S
S
A
Q.17 The commerical name of trichloroethene is: L
C
(A) Westron (B) Perclene (C) Westrosol (D) Orlone O
K
E
T
Q.18 The compound which has one isopropyl group is: E
R
(A) 2,2,3,3-tetramethyl pentane (B) 2,2-dimethyl pentane U
T
A
(C) 2,2,3-trimethyl pentane (D) 2-methyl pentane
L
C
N
E
Q.19 How many secondary carbon atoms does methyl cyclopropane have? M
O
(A) None (B) One (C) Two (D) Three N
0
2
of
Q.20 The IUPAC name of the compound CH −CH−CH is: 9
2 2 e
| | | g
a
P
OH OH OH
(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
L
Q.21 As per IUPAC rules, which one of the following groups, will be regarded as the principal functionalA
P
group? O
H
m B
.co (A) –C≡C– (B) –OH (C) −C||− (D) −C||−H 1 ,
s 8
e O O 8
ss 8
a 5
ocl Q.22 Which of the following is the first member of ester homologous series? 30
k 9
e (A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate(D) Ethyl methanoate 98
w.t 0
ww Q.23 The correct IUPAC name of 2-ethyl-3-pentyne is: 0,
0
(A) 3-methyl hexyne-4 (B) 4-ethyl pentyne-2 (C) 4-methyl hexyne-2 (D) None of these 0
: 0
e 0
bsit 32
we Q.24 IUPAC name for the compound is 5)-
m 75
0
fro (A) E-3-iodo-4-chloro-3-pentene (B) E-2-chloro-3-iodo-2-pentene H: (
e (C) Z-2-chloro-3-iodo-2-pentene (D) Z-3-iodo-4-chloro-3-pentene P
g )
ka Sir
ac Ph K.
udy P Q.25 The IUPAC name of the compound is CH3−C|H−C| H−NH2 (S. R.
d St CH3 RIYA
a (A) 1-amino-1-phenyl-2-methyl propane (B) 2-methyl-1-phenyl propane-1-amine A
o K
l
wn (C) 2-methyl-1-amino-1-phenyl propane (D) 1-isopropyl-1-phenyl methyl amine R.
o G
D Q.26 Which of the following compound is wrongly named? A
E (A) CH CH CH CHCOOH ; 2-Chloro pentanoic acid UH
E 3 2 2 S
FR C| l or :
t
c
e
r
(B) CH C≡CCHCOOH ; 2-Methyl hex-3-enoic acid Di
3 | S,
E
CH S
3 S
A
(C) CH CH CH=CHCOCH ; Hex-3-en-2-one L
3 2 3 C
O
(D) CH −CHCH CH CHO ; 4-Methyl pentanal
3 2 2 K
| E
T
CH
3
Q.27 The IUPAC name of the given compound is: E
R
U
T
A
L
C
N
(A) 1,1-dimethyl-3-hydroxy cyclohexane (B) 3,3-dimethyl-1-hydroxy cyclohexane E
M
(C) 3,3-dimethyl-1-cyclohexanol (D) 1,1-dimethyl-3-cyclohexanol O
N
0
2
of
Q.28 The IUPAC name of (C H ) NCH CH.COOH is: 10
2 5 2 2 e
| g
a
Cl P
(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
L
A
P
Q.29 The IUPAC name of the compound Br(Cl) CH. CF is: O
3 H
m (A) haloethane (B) 1,1,1-trifluoro-2-bromo-2-chloroethane B
.co (C) 2-bromo-2-chloro-1,1,1-trifluoroethane (D) 1-bromo-1-chloro-2,2,2-trifloro ethane 1 ,
s 8
e 8
ass Q.30 The group of hetrocylic compounds is: 58
ocl (A) Phenol, Furane (B) Furane, Thiophene (C) Thiophene, Phenol (D) Furane, Aniline 30
k 9
8
e 9
w.t 0
ww Q.31 The correct IUPAC name of CH3−CH2−C|| −COOH is: 0,
0
CH 0
: 2 0
e 0
bsit (A) 2-methyl butanoic acid (B) 2-ethyl-2-propenoic acid 32
we (C) 2-carboxy-1-butene (D) None of the above 5)-
m 75
Q.32 The IUPAC name of the following structure (CH )C.C.C.(CH )CH(CH ) is: 0
fro (A) 3-methyl-4-hexynene-2 (B3) 3-methyl-23-hexenyn3e-4 H: (
e P
g (C) 4-methyl-4-hexenyne-4 (D) all are correct )
ka Sir
ac Q.33 The IUPAC name of the following structure is [CH CH(CH )] C(CH CH )C(CH ) C(CH CH ) K.
dy P (A) 3,5-diethyl-4,6-dimethyl-5-[1-methylethyl]-3-he3ptene 3 2 2 3 3 2 3 2 S. R.
u (B) 3,5-diethyl-5-isopropyl-4,6-dimethyl-2-heptene (
t A
S (C) 3,5-diethyl-5-propyl-4,6-dimethyl-3-heptene Y
d RI
a (D) None of these A
o K
l
wn R.
o Q.34 and G
D A
E UH
E Number of secondary carbon atoms present in the above compounds are respectively: S
FR (A) 6,4,5 (B) 4,5,6 (C) 5,4,6 (D) 6,2,1 or :
t
c
e
Q.35 The IUPAC name of acetyl acetone is: r
Di
(A) 2,5-Pentane dione (B) 2,4-Pentane dione (C) 2,4-Hexane dione (D) 2,4-butane dione S,
E
S
S
Q.36 When vinyl & allyl are joined each other, we get A
L
(A) Conjugated alkadiene (B) comulative alkadiene C
(C) Isolated alkadiene (D) Allenes O
K
E
T