Identify the monochlorination product of isomeric alkane C5H12

Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields

i) A single monochloride

ii) Three isomeric monochlorides

iii) Four isomeric monochlorides.

 
Prerequisite Reading: Structural Isomerism, Types of Hydrogen, Free radical halogenation
 
The compound C5H12 is a saturated alkane following the general formula of CnH2n+2, where n is the number of Carbon atoms. The different chain isomers that are possible for the given molecular formula are-
 
a) n-pentane
n-pentane structure
 
b) Isopentane
isopentane_structure
 
c) Neo-pentane
neopentane structure
 
Depending on the number of types of Hydrogen present, the chain isomers on photochemical chlorination will yield single or multiple monochlorinated positional isomers - 
 
 a) n-pentane has three types of hydrogen that on monochlorination gives 1-chloropentane, 2-chloropentane, and 3-chloropentane.
 
halogenation products of n pentane
b) Isopentane has four types of hydrogen that on monochlorination gives 1-chloro-3-methylbutane, 2-chloro-3-methylbutane, 2-chloro-2-methylbutane, 1-chloro-2-methylbutane.
 
halogenation products of isopentane
 
c) Neopentane has one type of hydrogen that on monochlorination gives 1-chloro-2,2-dimethylbutane.
 
neopentane halogenation products

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