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Chapter 9: Q114P (page 391)

Explain why the rate of the reaction of 1-bromo-2-butene with ethanol is increased if silver nitrate is added to the reaction mixture.

Short Answer

Expert verified

AgBr being an ionic compound, forms Ag+ in the solution which facilitates the formation of carbocation by forming AgBr after reaction. Thus, in presence of AgBr, the SN1 reaction facilitates.

Step by step solution

01

Statement

1-bromo-2-butene with ethanol undergoes SN1 reaction where the C-Br bond breaks first and forming the stable carbocation, The nucleophile attacks to form a racemic mixture of dl configuration.

02

Definition of SN1 reaction

SN1 reaction is a nucleophilic substitution reaction which form carbocation in 1st step before the breaking of C-halogen bond. It shows a carbocation like transition state.

A reaction mechanism with an experimental compound is given below.

03

Explanation

As AgNO3 assist the reaction forming the AgBr compound, the SN1 reaction facilitated in presence of AgNO3.

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Most popular questions from this chapter

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

b. -OCN or -SCN

c. Cl- or Br-

d. CH3S- or CH3O-

If 2-fluoropentane were to undergo an E1 reaction, would you expect the major product to be the more stable alkene or the less stable alkene? Explain your answer.

What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3- methyl pentane:

a. with HO-?

b. with H2O?

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

c. How would the products differ if the starting material were the trans isomer? Are these products optically active?

d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly?

e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?

What products are formed when the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion?
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