Question

Propose structures for compounds that fit the following description a. An alkyl halide that gives a mixture of three different alkenes in an E2 reaction b. An organic halide that will not undergo nucleophilic substitution

Answer 1

An alkyl halide that gives a mixture of three different alkenes in an E2 reaction could be 2-bromo-2-methylpentane, while a tertiary alkyl halide like tertiary butyl chloride (2-chloro-2-methylpropane) would not easily undergo nucleophilic substitution due to steric hindrance.

Step-by-step explanation:

To propose structures for compounds fitting specific descriptions in organic chemistry, we need to consider the molecular geometry and reactivity of functional groups. For an alkyl halide that gives a mixture of three different alkenes in an E2 reaction, we must consider an alkyl halide with halogen on a carbon that is connected to at least two other carbons having at least one hydrogen each to be eliminated along with the halogen.

A suitable example would be 2-bromo-2-methylpentane. Upon undergoing an E2 reaction, this compound could yield three alkenes: 2-methyl-2-pentene, 3-methyl-2-pentene, and 2-methyl-1-pentene due to the possible formation of a double bond at different positions after the elimination of bromine and hydrogen.

For an organic halide that will not undergo nucleophilic substitution, a compound like tertiary butyl chloride (2-chloro-2-methylpropane) is ideal. Its highly hindered tertiary carbon atom makes it difficult for a nucleophile to access the electrophilic carbon, therefore, greatly reducing the likelihood of a substitution reaction.