The remaining 5% corresponds to substitution of methyl hydrogens at C1 and C12. The
proportion of 1chlorododecane in the monochloride fraction is 5%.
4.42
(
a
)
Two of the monochlorides derived from chlorination of 2,2,4trimethylpentane are primary
chlorides:
The two remaining isomers are a secondary chloride and a tertiary chloride:
(
b
)
Substitution of any one of the nine hydrogens designated as
x
in the structural diagram yields
1chloro2,2,4trimethylpentane. Substitution of any one of the six hydrogens designated as
y
gives 1chloro2,4,4trimethylpentane.
Assuming equal reactivity of a single
x
hydrogen and a single
y
hydrogen, the ratio of the two
isomers is then expected to be 9:6. Since together the two primary chlorides total 65% of the
monochloride fraction, there will be 39% 1chloro2,2,4trimethylpentane (substitution of
x
)
and 26% 1chloro2,4,4trimethylpentane (substitution of
y
).
4.43
The three monochlorides are shown in the equation
Pentane has six primary hydrogens (two CH
3
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 Spring '01
 Reynolds
 Organic chemistry, 5%, 25%, Pentane, CH3 CH3

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