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Question

a) Rank the SN2 reaction rates for the following compounds: Rank the S_N 2 reaction rates for the following compounds:

fastest rate slowest rate 1-chloro-3-methylpentane, 2-chloro-3-methylpentane, 3-chloro-3-methylpentane, Chloromethane

b) Rank the S_N2 reaction rates for the following compounds:

fastest rate slowest rate 2-bromo-3-methylbutane, 1-bromo-3-methylbutane, bromomethane, 2-bromo-2-methybutane

Nucleophilic Substitution Bimolecular:

Nucleophilic substitution bimolecular reactions involve the simultaneous leaving of the group and attaching of the incoming nucleophile, resulting in the transition state in which carbon is pentavalent, with four groups bonded to the carbon atom.

Answer “Rank the S_N2 reaction rates for the following compounds:”

Explanation

Alkyl halides undergo nucleophilic substitution bimolecular reaction. This involves the simultaneous attachment of the nucleophile and the leaving group. The S_N2 reactions will be most successful for the alkylhalides with the lowest steric hindrance.

Primary alkyl halides react the fastest to S_N2 reactions, while tertiary and secondary alkyl halides react the least.

This primary alkylhalide is called a primary alkyl. The carbon to which the chlorine is attached is directly bound with one carbon atom.

This secondary alkylhalide is because the carbon to which the chlorine is attached is directly bound to two carbon atoms.

This is a tertiary halide of alkyl halides, as the carbon atom to chlorine is directly bonded with three other carbon atoms.

This alkyl halide is the least affected, since the carbon to the which the chlorine atom is attached has not been bonded with any other carbon.

Answer

This is why the order in which alkyl halidides react less to nucleophilic substitution bimolecular reaction is reversed.

a) chloromethane > 1−chloro−3−methylpentane > 2−chloro−3−methylpentane > 3−chloro−3−methylpentane

b) Bromomethane > 1-bromo-3-methylbutane > 2-bromo-3-methylbutane > 2-bromo-2-methybutane

Last words

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