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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:What products would you expect from the reaction of 1-bromopropane with each of the following?

(b) KOC(CH3)

Organic solvents like benzene, ether, and chloroform are neither protic nor strongly polar. What effect would you expect these solvents to have on the reactivity of a nucleophile in SN2 reactions?

Question: Order each of the following sets of compounds with respect to reactivity:

c. CH3CH2 CH2OCH3 CH3CH2 CH2OTs CH3CH2 CH2Br

The following Walden cycle has been carried out. Explain the results, and indicate where Walden inversion occurs.

Which reactant in each of the following pairs is more nucleophilic? Explain.

(e) I- or Cl-
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