ORGANIC CHEMISTRY- NOMENCLATURE AND ISOMERISM

Nomenclature of organic compounds :

(i)

(ii)

(iiii)

(iv)

(v)

(vi)

(vii)

(viii)

(ix)

(x)

(xi)
(xii)

(xiii) OCOCH(CH3)CH3

(xiv)
CH2CH2CHO
(xv) CH3
C 2 H5 .NH2

Answers
i) 2-Ethyl-2-methylpentan-1-ol (Functional group is included even though chain length becomes shorter)
ii) 2-Ethylbutanoic acid
iii) 2-Ethyl-4,4 – dimethylpentanal
iv) 2,2-Dimethylpropan-1-ol (Priority is given to the functional group)
v) Ethyl-4-chloro-3-methylpentanoate
vi) 4-Oxo-butanoic acid
vii) Hexanedial ( Numbers are not indicated as – CHO group is always terminal)
viii) Pent-4-en-2-ol (Priority is given to the functional group over a multiple bond)
ix) But-3-enoic acid
x) 5-Oxohexanal
xi) 4-Chloropenta-1,3-diene
xii) 2,4 – Dimethylhexa-1,3,5- triene
xiii) Phenyl-2 methyl propanoate.
xiv) 2-Phenyl propanal
xv) 4-Ethyl-3-methylbenzamine or 4-Ethyl-3-methylaniline

ISOMERISM

Questions :
1. Write all the chain isomers of C5H12.
2. Show the position isomers of (i) C4H8 (ii) C3H7OH.
3. Write the functional group isomers of -
(i) C3H8O (2-alcoholic and 1- etheric)
 (ii) C3H6O ( 1- aldehydic and 1- Ketonic)
(iii) C3H6O2 (1- carboxylic and 2- esteric)
4. Show the metameric structures of the following compounds :
(i) CH3 - CH2 - O – CH2 – CH3 (Ethoxyethane)

(ii) (Pentan-2-one)
(iii) CH3 – NH – CH2 – CH2 – CH3 (N-Methylpropanamine)
5. Show the keto form of the following enols :

(i) (ii)
6. Draw all the possible isomers of C4H10O and write the number of total functional group isomers.

Answers

1. CH3 – CH2 – CH2 – CH2 – CH3

n – Pentane iso-Pentane
IUPAC : Pentane IUPAC : 2-methylbutane

Neo- Pentane
IUPAC : 2, 2 – Dimethylpropane

2,(i)
But-2-ene But-1-ene

(ii)
Propan-1-ol Propan-2-ol

3.
Propan-1-ol Propan-2-ol Methoxy-ethane

(ii) CH3 – CH2 – CHO

Propanal Propanone
(iii) CH3 – CH2 – COOH CH3COOCH3 HCOOC2H5
Propanoic acid Methyl ethanoate Ethyl methanoate

4.(i) CH3 – O – CH2 – CH2 – CH3( Methoxy propane)

(ii) (Pentan-3-one)
(iii) N-Ethyl ethanamine

5. (i) , (ii)
6.(i) CH3 – CH2 – CH2 – CH2 – OH (Butan-1-ol)

(ii) (Butan-2-ol)

(iii) (2-Mthylpropan-1-ol)

(iv) (2-Methylpropan-2-ol)
(v) CH3 – CH2 – O – CH2 – CH3(Ethoxyethane)
(vi) CH3 – O – CH2 – CH2 – CH3 (1-Methoxy propane)
(vii)

(2-Methoxypropane)
(i) and (ii); (iii) and (iv) ; (vi) and (vii) are position isomers.
(i) and (iii); (ii) and (iv) are the chain isomers.