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Chapter 11: Q11 P. (page 329)

Rank the following substances in order of their expected SN1reactivity:

Short Answer

Expert verified

The SN1 reaction is a nucleophilic substitution reaction where carbon-halogen bond is broken which results in positively charged carbon, and then nucleophile attacks the carbocation and forms a new bond. Only one reacting species is involved in the rate determining step of the reaction. The termSN1 stands for substitution nucleophilic unimolecular. The hydrolysis of tert-butyl bromide with aqueous NaOH solution is an example ofSN1 reaction.

Step by step solution

01

Nucleophilic unimolecular substitution reaction SN1

The SN1 reaction is a nucleophilic substitution reaction where carbon-halogen bond is broken which results in positively charged carbon, and then nucleophile attacks the carbocation and forms a new bond. Only one reacting species is involved in the rate determining step of the reaction. The termSN1 stands for substitution nucleophilic unimolecular. The hydrolysis of tert-butyl bromide with aqueous NaOH solution is an example ofSN1 reaction.

02

Order of the expected SN1 reactivity

SN1reactivity is related to carbocation stability. Thus, substrates from the most stable carbocations are the most reactive in reactions.

Least reactive →Most reactive

vinylic primary secondary allylic

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Most popular questions from this chapter

Propose a structure for an alkyl halide that gives only (E)-3-methyl-2-phenyl-2-pentene on E2elimination. Make sure you indicate the stereochemistry.

Question: Propose structures for compounds that fit the following descriptions:

(b) An organohalide that will not undergo nucleophilic substitution

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