If one hydrogen in a hydrocarbon is replaced by a halogen atom, the number of isomers

Chapter 22, Problem 22.67

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If one hydrogen in a hydrocarbon is replaced by a halogen atom, the number of isomers that exist for the substituted compound depends on the number of types of hydrogen in the original hydrocarbon. Thus there is only one form of chloroethane (all hydrogens in ethane are equivalent), but there are two isomers of propane that arise from the substitution of a methyl hydrogen or a methylene hydrogen. How many isomers can be obtained when one hydrogen in each of the compounds named below is replaced by a chlorine atom? a. n-pentane c. 2,4-dimethylpentane b. 2-methylbutane d. methylcyclobutane

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