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Chapter 11: Q12 P. (page 329)

3-Bromo-1-butene and 1-bromo-2-butene undergoSN1 reaction at nearly the same rate, even though one is a secondary halide and the other is primary. Explain.

Short Answer

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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

3-Bromo-1-butene and 1-bromo-2-butene undergo SN1 reaction

The two bromobutene from the same allylic carbocation in the rate limiting step is shown below.

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Most popular questions from this chapter

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

(d) An alcohol that reacts rapidly with HCl at 0 °C

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

a) CN-

Assign configuration to the following substance, and draw the structure of the product that would result from nucleophilic substitution reaction with (reddish brown =Br):

We saw in Section 8-7 that bromohydrins are converted into epoxides when treated with base. Propose a mechanism, using curved arrows to show the electron flow.

What effect would you expect the following changes to have on the rate of thereaction of 1-iodo-2-methylbutane with cyanide ion?

(b) Both theand the 1-iodo-2-methylbutane concentrations are tripled.

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