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Portmess Homework Q&S 90

Portmess Homework Q&S 90 - 84 ALCOHOLS AND ALKYL...

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The remaining 5% corresponds to substitution of methyl hydrogens at C-1 and C-12. The proportion 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 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 1-chloro-2,2,4-trimethylpentane. Substitution of any one of the six hydrogens designated as y gives 1-chloro-2,4,4-trimethylpentane. 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% 1-chloro-2,2,4-trimethylpentane (substitution of x ) and 26% 1-chloro-2,4,4-trimethylpentane (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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