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Among the isomeric alkanes of molecular formula \(\mathrm{C}_5 \mathrm{H}_{12}\), identify the one that on photochemical chlorination yields
(i) A single monochloride.
(ii) Three isomeric monochlorides.
(iii) Four isomeric monochlorides.
(i) A single monochloride.
(ii) Three isomeric monochlorides.
(iii) Four isomeric monochlorides.
Solution:
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Verified Answer
(i) Neopentane, 
As all the H-atoms are equivalent, the replacement of any one of them gives the same product.
(ii) \(\stackrel{a}{\mathrm{CH}_3} \stackrel{b}{\mathrm{CH}_2} \stackrel{c}{\mathrm{CH}_2} \stackrel{d}{\mathrm{CH}_2} \stackrel{e}{\mathrm{CH}_3} n\)-pentane. \(a, b, c\) are the three sets of equivalent hydrogens. Therefore, three isomeric monochlorides are possible.
(iii)
iso-pentane. There are four sets of equivalent hydrogens Designated as a, b, c, d. Thus, four isomeric monochlorides are possible.
As all the H-atoms are equivalent, the replacement of any one of them gives the same product.
(ii) \(\stackrel{a}{\mathrm{CH}_3} \stackrel{b}{\mathrm{CH}_2} \stackrel{c}{\mathrm{CH}_2} \stackrel{d}{\mathrm{CH}_2} \stackrel{e}{\mathrm{CH}_3} n\)-pentane. \(a, b, c\) are the three sets of equivalent hydrogens. Therefore, three isomeric monochlorides are possible.
(iii)
iso-pentane. There are four sets of equivalent hydrogens Designated as a, b, c, d. Thus, four isomeric monochlorides are possible.
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