The remaining 5% corresponds to substitution of methyl hydrogens at C-1 and C-12. Theproportion of 1-chlorododecane in the monochloride fraction is 5%.4.42(a)Two of the monochlorides derived from chlorination of 2,2,4-trimethylpentane are primarychlorides:The two remaining isomers are a secondary chloride and a tertiary chloride:(b)Substitution of any one of the nine hydrogens designated as xin the structural diagram yields1-chloro-2,2,4-trimethylpentane. Substitution of any one of the six hydrogens designated as ygives 1-chloro-2,4,4-trimethylpentane.Assuming equal reactivity of a single x hydrogen and a single yhydrogen, the ratio of the twoisomers is then expected to be 9:6. Since together the two primary chlorides total 65% of themonochloride fraction, there will be 39% 1-chloro-2,2,4-trimethylpentane (substitution of x)and 26% 1-chloro-2,4,4-trimethylpentane (substitution of y).4.43The three monochlorides are shown in the equationPentane has six primary hydrogens (two CH3
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